Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline JetBlue Airways

The cheapest airline(s) flying from Chicago to Boston is JetBlue Airways.

  • JetBlue Airways JetBlue Airways
  • United Airlines United Airlines
  • American Airlines American Airlines
  • Spirit Airlines Spirit Airlines
  • Frontier Airlines Frontier Airlines
  • Southwest Airlines Southwest Airlines
  • Sun Country Airlines Sun Country Airlines
  • Air New Zealand Air New Zealand
  • Alaska Airlines Alaska Airlines
Cheapest Month March

Travel Period: January 2025 - December 2025

The cheapest month(s) to fly from Chicago to Boston is March.

  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
Cheapest Day of the Week Tuesday

The cheapest day(s) of the week to fly from Chicago to Boston is Tuesday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Mon, 2 Dec, 2024

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    • Airline Filter by Airline
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      • Availability
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 18:05 ORD
        21:30 BOS
        2Hrs, 25m Direct
      • ORDChicago O'Hare International Airport 18:05 - BOS 21:30 2h 25m Direct
      • ORDChicago O'Hare International Airport 18:05
      • BOSBoston Logan International Airport 21:30
      • 2h 25m
      • Direct
      • United Airlines (UA 1742)Boeing 737 Max 8 Passenger
      • United Airlines (UA 1742)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 18:05 ORD
        21:30 BOS
        2Hrs, 25m Direct
      • ORDChicago O'Hare International Airport 18:05 - BOS 21:30 2h 25m Direct
      • ORDChicago O'Hare International Airport 18:05
      • BOSBoston Logan International Airport 21:30
      • 2h 25m
      • Direct
      • United Airlines (UA 1742)Airbus A321 Neo
      • United Airlines (UA 1742)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Airbus A321 Neo
      • 18:25 ORD
        21:54 BOS
        2Hrs, 29m Direct
      • ORDChicago O'Hare International Airport 18:25 - BOS 21:54 2h 29m Direct
      • ORDChicago O'Hare International Airport 18:25
      • BOSBoston Logan International Airport 21:54
      • 2h 29m
      • Direct
      • United Airlines (UA 715)Boeing 737 800
      • United Airlines (UA 715)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 18:25 MDW
        21:35 BOS
        2Hrs, 10m Direct
      • MDWChicago Midway Airport 18:25 - BOS 21:35 2h 10m Direct
      • MDWChicago Midway Airport 18:25
      • BOSBoston Logan International Airport 21:35
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 1933)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1933)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 20:20 ORD
        23:44 BOS
        2Hrs, 24m Direct
      • ORDChicago O'Hare International Airport 20:20 - BOS 23:44 2h 24m Direct
      • ORDChicago O'Hare International Airport 20:20
      • BOSBoston Logan International Airport 23:44
      • 2h 24m
      • Direct
      • American Airlines (AA 4400)Embraer Emb 175
      • American Airlines (AA 4400)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Embraer Emb 175
      • 20:25 MDW
        23:35 BOS
        2Hrs, 10m Direct
      • MDWChicago Midway Airport 20:25 - BOS 23:35 2h 10m Direct
      • MDWChicago Midway Airport 20:25
      • BOSBoston Logan International Airport 23:35
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 1350)Boeing 737 700
      • Southwest Airlines (WN 1350)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 700
      • 20:25 MDW
        23:35 BOS
        2Hrs, 10m Direct
      • MDWChicago Midway Airport 20:25 - BOS 23:35 2h 10m Direct
      • MDWChicago Midway Airport 20:25
      • BOSBoston Logan International Airport 23:35
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 2229)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2229)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 20:30 ORD
        00:15 BOS
        2Hrs, 45m Direct
      • ORDChicago O'Hare International Airport 20:30 - BOS 00:15 2h 45m Direct
      • ORDChicago O'Hare International Airport 20:30
      • BOSBoston Logan International Airport 00:15
      • 2h 45m
      • Direct
      • American Airlines (AA 4400)Embraer Emb 175
      • American Airlines (AA 4400)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Embraer Emb 175
      • 20:30 MDW
        23:40 BOS
        2Hrs, 10m Direct
      • MDWChicago Midway Airport 20:30 - BOS 23:40 2h 10m Direct
      • MDWChicago Midway Airport 20:30
      • BOSBoston Logan International Airport 23:40
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 2229)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2229)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 21:30 ORD
        00:54 BOS
        2Hrs, 24m Direct
      • ORDChicago O'Hare International Airport 21:30 - BOS 00:54 2h 24m Direct
      • ORDChicago O'Hare International Airport 21:30
      • BOSBoston Logan International Airport 00:54
      • 2h 24m
      • Direct
      • United Airlines (UA 2627)Boeing 737 800
      • United Airlines (UA 2627)
        • -
        • -
        • -
        • T
        • -
        • -
        • S
      • Boeing 737 800
      • 21:30 ORD
        00:54 BOS
        2Hrs, 24m Direct
      • ORDChicago O'Hare International Airport 21:30 - BOS 00:54 2h 24m Direct
      • ORDChicago O'Hare International Airport 21:30
      • BOSBoston Logan International Airport 00:54
      • 2h 24m
      • Direct
      • United Airlines (UA 2627)Boeing 737 700
      • United Airlines (UA 2627)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Boeing 737 700
      • 21:30 ORD
        00:54 BOS
        2Hrs, 24m Direct
      • ORDChicago O'Hare International Airport 21:30 - BOS 00:54 2h 24m Direct
      • ORDChicago O'Hare International Airport 21:30
      • BOSBoston Logan International Airport 00:54
      • 2h 24m
      • Direct
      • United Airlines (UA 2627)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2627)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 06:20 MDW
        09:35 BOS
        2Hrs, 15m Direct
      • MDWChicago Midway Airport 06:20 - BOS 09:35 2h 15m Direct
      • MDWChicago Midway Airport 06:20
      • BOSBoston Logan International Airport 09:35
      • 2h 15m
      • Direct
      • Southwest Airlines (WN 240)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 240)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 06:25 MDW
        09:40 BOS
        2Hrs, 15m Direct
      • MDWChicago Midway Airport 06:25 - BOS 09:40 2h 15m Direct
      • MDWChicago Midway Airport 06:25
      • BOSBoston Logan International Airport 09:40
      • 2h 15m
      • Direct
      • Southwest Airlines (WN 2229)Boeing 737 700
      • Southwest Airlines (WN 2229)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 700
      • 07:00 ORD
        10:28 BOS
        2Hrs, 28m Direct
      • ORDChicago O'Hare International Airport 07:00 - BOS 10:28 2h 28m Direct
      • ORDChicago O'Hare International Airport 07:00
      • BOSBoston Logan International Airport 10:28
      • 2h 28m
      • Direct
      • American Airlines (AA 3703)Embraer Emb 175
      • American Airlines (AA 3703)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Embraer Emb 175
      • 07:19 ORD
        10:50 BOS
        2Hrs, 31m Direct
      • ORDChicago O'Hare International Airport 07:19 - BOS 10:50 2h 31m Direct
      • ORDChicago O'Hare International Airport 07:19
      • BOSBoston Logan International Airport 10:50
      • 2h 31m
      • Direct
      • American Airlines (AA 3703)Embraer Emb 175
      • American Airlines (AA 3703)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • Embraer Emb 175
      • 07:20 ORD
        10:54 BOS
        2Hrs, 34m Direct
      • ORDChicago O'Hare International Airport 07:20 - BOS 10:54 2h 34m Direct
      • ORDChicago O'Hare International Airport 07:20
      • BOSBoston Logan International Airport 10:54
      • 2h 34m
      • Direct
      • American Airlines (AA 3703)Embraer Emb 175
      • American Airlines (AA 3703)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Embraer Emb 175
      • 07:30 ORD
        10:49 BOS
        2Hrs, 19m Direct
      • ORDChicago O'Hare International Airport 07:30 - BOS 10:49 2h 19m Direct
      • ORDChicago O'Hare International Airport 07:30
      • BOSBoston Logan International Airport 10:49
      • 2h 19m
      • Direct
      • United Airlines (UA 592)Airbus A321 Neo
      • United Airlines (UA 592)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • Airbus A321 Neo
      • 07:46 ORD
        11:12 BOS
        2Hrs, 26m Direct
      • ORDChicago O'Hare International Airport 07:46 - BOS 11:12 2h 26m Direct
      • ORDChicago O'Hare International Airport 07:46
      • BOSBoston Logan International Airport 11:12
      • 2h 26m
      • Direct
      • United Airlines (UA 1450)Boeing 737 700
      • United Airlines (UA 1450)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Boeing 737 700
      • 08:00 MDW
        11:15 BOS
        2Hrs, 15m Direct
      • MDWChicago Midway Airport 08:00 - BOS 11:15 2h 15m Direct
      • MDWChicago Midway Airport 08:00
      • BOSBoston Logan International Airport 11:15
      • 2h 15m
      • Direct
      • Southwest Airlines (WN 2666)Boeing 737 800
      • Southwest Airlines (WN 2666)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 800
      • 08:05 ORD
        11:26 BOS
        2Hrs, 21m Direct
      • ORDChicago O'Hare International Airport 08:05 - BOS 11:26 2h 21m Direct
      • ORDChicago O'Hare International Airport 08:05
      • BOSBoston Logan International Airport 11:26
      • 2h 21m
      • Direct
      • American Airlines (AA 314)Boeing 737 800
      • American Airlines (AA 314)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 800
      • 08:12 ORD
        11:27 BOS
        2Hrs, 15m Direct
      • ORDChicago O'Hare International Airport 08:12 - BOS 11:27 2h 15m Direct
      • ORDChicago O'Hare International Airport 08:12
      • BOSBoston Logan International Airport 11:27
      • 2h 15m
      • Direct
      • American Airlines (AA 314)Boeing 737 800
      • American Airlines (AA 314)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 08:20 ORD
        11:43 BOS
        2Hrs, 23m Direct
      • ORDChicago O'Hare International Airport 08:20 - BOS 11:43 2h 23m Direct
      • ORDChicago O'Hare International Airport 08:20
      • BOSBoston Logan International Airport 11:43
      • 2h 23m
      • Direct
      • American Airlines (AA 314)Boeing 737 800
      • American Airlines (AA 314)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • Boeing 737 800
      • 08:30 MDW
        11:45 BOS
        2Hrs, 15m Direct
      • MDWChicago Midway Airport 08:30 - BOS 11:45 2h 15m Direct
      • MDWChicago Midway Airport 08:30
      • BOSBoston Logan International Airport 11:45
      • 2h 15m
      • Direct
      • Southwest Airlines (WN 2666)Boeing 737 700
      • Southwest Airlines (WN 2666)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 08:42 ORD
        12:11 BOS
        2Hrs, 29m Direct
      • ORDChicago O'Hare International Airport 08:42 - BOS 12:11 2h 29m Direct
      • ORDChicago O'Hare International Airport 08:42
      • BOSBoston Logan International Airport 12:11
      • 2h 29m
      • Direct
      • JetBlue Airways (B6 312)Embraer Emb E90
      • JetBlue Airways (B6 312)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Embraer Emb E90
      • 08:51 ORD
        12:13 BOS
        2Hrs, 22m Direct
      • ORDChicago O'Hare International Airport 08:51 - BOS 12:13 2h 22m Direct
      • ORDChicago O'Hare International Airport 08:51
      • BOSBoston Logan International Airport 12:13
      • 2h 22m
      • Direct
      • JetBlue Airways (B6 312)Airbus A220 300
      • JetBlue Airways (B6 312)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Airbus A220 300
      • 09:20 ORD
        12:46 BOS
        2Hrs, 26m Direct
      • ORDChicago O'Hare International Airport 09:20 - BOS 12:46 2h 26m Direct
      • ORDChicago O'Hare International Airport 09:20
      • BOSBoston Logan International Airport 12:46
      • 2h 26m
      • Direct
      • United Airlines (UA 2099)Airbus
      • United Airlines (UA 2099)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Airbus
      • 09:20 ORD
        12:45 BOS
        2Hrs, 25m Direct
      • ORDChicago O'Hare International Airport 09:20 - BOS 12:45 2h 25m Direct
      • ORDChicago O'Hare International Airport 09:20
      • BOSBoston Logan International Airport 12:45
      • 2h 25m
      • Direct
      • United Airlines (UA 217)Boeing 737 900
      • United Airlines (UA 217)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 900
      • 09:20 ORD
        12:46 BOS
        2Hrs, 26m Direct
      • ORDChicago O'Hare International Airport 09:20 - BOS 12:46 2h 26m Direct
      • ORDChicago O'Hare International Airport 09:20
      • BOSBoston Logan International Airport 12:46
      • 2h 26m
      • Direct
      • United Airlines (UA 2099)Boeing 737 800
      • United Airlines (UA 2099)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 800
      • 09:30 MDW
        12:40 BOS
        2Hrs, 10m Direct
      • MDWChicago Midway Airport 09:30 - BOS 12:40 2h 10m Direct
      • MDWChicago Midway Airport 09:30
      • BOSBoston Logan International Airport 12:40
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 2666)Boeing 737 800
      • Southwest Airlines (WN 2666)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 09:45 MDW
        12:55 BOS
        2Hrs, 10m Direct
      • MDWChicago Midway Airport 09:45 - BOS 12:55 2h 10m Direct
      • MDWChicago Midway Airport 09:45
      • BOSBoston Logan International Airport 12:55
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 5421)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 5421)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 Max 8 Passenger
      • 10:37 ORD
        14:02 BOS
        2Hrs, 25m Direct
      • ORDChicago O'Hare International Airport 10:37 - BOS 14:02 2h 25m Direct
      • ORDChicago O'Hare International Airport 10:37
      • BOSBoston Logan International Airport 14:02
      • 2h 25m
      • Direct
      • United Airlines (UA 399)Boeing 737 Max 8 Passenger
      • United Airlines (UA 399)
        • M
        • T
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 10:37 ORD
        14:02 BOS
        2Hrs, 25m Direct
      • ORDChicago O'Hare International Airport 10:37 - BOS 14:02 2h 25m Direct
      • ORDChicago O'Hare International Airport 10:37
      • BOSBoston Logan International Airport 14:02
      • 2h 25m
      • Direct
      • United Airlines (UA 399)Boeing 737 700
      • United Airlines (UA 399)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 700
      • 10:55 ORD
        14:22 BOS
        2Hrs, 27m Direct
      • ORDChicago O'Hare International Airport 10:55 - BOS 14:22 2h 27m Direct
      • ORDChicago O'Hare International Airport 10:55
      • BOSBoston Logan International Airport 14:22
      • 2h 27m
      • Direct
      • United Airlines (UA 399)Airbus
      • United Airlines (UA 399)
        • -
        • -
        • -
        • -
        • F
        • S
        • S
      • Airbus
      • 10:55 ORD
        14:22 BOS
        2Hrs, 27m Direct
      • ORDChicago O'Hare International Airport 10:55 - BOS 14:22 2h 27m Direct
      • ORDChicago O'Hare International Airport 10:55
      • BOSBoston Logan International Airport 14:22
      • 2h 27m
      • Direct
      • United Airlines (UA 399)Boeing 737 900
      • United Airlines (UA 399)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 900
      • 12:00 ORD
        15:18 BOS
        2Hrs, 18m Direct
      • ORDChicago O'Hare International Airport 12:00 - BOS 15:18 2h 18m Direct
      • ORDChicago O'Hare International Airport 12:00
      • BOSBoston Logan International Airport 15:18
      • 2h 18m
      • Direct
      • American Airlines (AA 2460)Boeing 737 800
      • American Airlines (AA 2460)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 800
      • 12:00 ORD
        15:15 BOS
        2Hrs, 15m Direct
      • ORDChicago O'Hare International Airport 12:00 - BOS 15:15 2h 15m Direct
      • ORDChicago O'Hare International Airport 12:00
      • BOSBoston Logan International Airport 15:15
      • 2h 15m
      • Direct
      • American Airlines (AA 2501)Boeing 737 800
      • American Airlines (AA 2501)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 12:00 ORD
        15:18 BOS
        2Hrs, 18m Direct
      • ORDChicago O'Hare International Airport 12:00 - BOS 15:18 2h 18m Direct
      • ORDChicago O'Hare International Airport 12:00
      • BOSBoston Logan International Airport 15:18
      • 2h 18m
      • Direct
      • American Airlines (AA 1570)Boeing 737 800
      • American Airlines (AA 1570)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 800
      • 13:35 ORD
        16:52 BOS
        2Hrs, 17m Direct
      • ORDChicago O'Hare International Airport 13:35 - BOS 16:52 2h 17m Direct
      • ORDChicago O'Hare International Airport 13:35
      • BOSBoston Logan International Airport 16:52
      • 2h 17m
      • Direct
      • American Airlines (AA 2877)Boeing 737 800
      • American Airlines (AA 2877)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 13:43 ORD
        16:56 BOS
        2Hrs, 13m Direct
      • ORDChicago O'Hare International Airport 13:43 - BOS 16:56 2h 13m Direct
      • ORDChicago O'Hare International Airport 13:43
      • BOSBoston Logan International Airport 16:56
      • 2h 13m
      • Direct
      • American Airlines (AA 2877)Boeing 737 800
      • American Airlines (AA 2877)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 13:55 ORD
        17:16 BOS
        2Hrs, 21m Direct
      • ORDChicago O'Hare International Airport 13:55 - BOS 17:16 2h 21m Direct
      • ORDChicago O'Hare International Airport 13:55
      • BOSBoston Logan International Airport 17:16
      • 2h 21m
      • Direct
      • United Airlines (UA 580)Airbus A321 Neo
      • United Airlines (UA 580)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Airbus A321 Neo
      • 13:55 ORD
        17:13 BOS
        2Hrs, 18m Direct
      • ORDChicago O'Hare International Airport 13:55 - BOS 17:13 2h 18m Direct
      • ORDChicago O'Hare International Airport 13:55
      • BOSBoston Logan International Airport 17:13
      • 2h 18m
      • Direct
      • United Airlines (UA 580)Airbus A321 Neo
      • United Airlines (UA 580)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • Airbus A321 Neo
      • 13:55 ORD
        17:18 BOS
        2Hrs, 23m Direct
      • ORDChicago O'Hare International Airport 13:55 - BOS 17:18 2h 23m Direct
      • ORDChicago O'Hare International Airport 13:55
      • BOSBoston Logan International Airport 17:18
      • 2h 23m
      • Direct
      • United Airlines (UA 580)Boeing 737 800
      • United Airlines (UA 580)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 800
      • 14:14 ORD
        17:33 BOS
        2Hrs, 19m Direct
      • ORDChicago O'Hare International Airport 14:14 - BOS 17:33 2h 19m Direct
      • ORDChicago O'Hare International Airport 14:14
      • BOSBoston Logan International Airport 17:33
      • 2h 19m
      • Direct
      • American Airlines (AA 2877)Boeing 737 800
      • American Airlines (AA 2877)
        • M
        • T
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 14:20 MDW
        17:30 BOS
        2Hrs, 10m Direct
      • MDWChicago Midway Airport 14:20 - BOS 17:30 2h 10m Direct
      • MDWChicago Midway Airport 14:20
      • BOSBoston Logan International Airport 17:30
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 4815)Boeing 737 800
      • Southwest Airlines (WN 4815)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 800
      • 14:55 MDW
        18:05 BOS
        2Hrs, 10m Direct
      • MDWChicago Midway Airport 14:55 - BOS 18:05 2h 10m Direct
      • MDWChicago Midway Airport 14:55
      • BOSBoston Logan International Airport 18:05
      • 2h 10m
      • Direct
      • Southwest Airlines (WN 3701)Boeing 737 800
      • Southwest Airlines (WN 3701)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • Boeing 737 800
      • 15:50 ORD
        19:11 BOS
        2Hrs, 21m Direct
      • ORDChicago O'Hare International Airport 15:50 - BOS 19:11 2h 21m Direct
      • ORDChicago O'Hare International Airport 15:50
      • BOSBoston Logan International Airport 19:11
      • 2h 21m
      • Direct
      • United Airlines (UA 470)Boeing 737 800
      • United Airlines (UA 470)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 15:55 MDW
        19:10 BOS
        2Hrs, 15m Direct
      • MDWChicago Midway Airport 15:55 - BOS 19:10 2h 15m Direct
      • MDWChicago Midway Airport 15:55
      • BOSBoston Logan International Airport 19:10
      • 2h 15m
      • Direct
      • Southwest Airlines (WN 1933)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1933)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 16:40 ORD
        20:02 BOS
        2Hrs, 22m Direct
      • ORDChicago O'Hare International Airport 16:40 - BOS 20:02 2h 22m Direct
      • ORDChicago O'Hare International Airport 16:40
      • BOSBoston Logan International Airport 20:02
      • 2h 22m
      • Direct
      • JetBlue Airways (B6 612)Embraer Emb E90
      • JetBlue Airways (B6 612)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • Embraer Emb E90
      • 17:44 ORD
        21:00 BOS
        2Hrs, 16m Direct
      • ORDChicago O'Hare International Airport 17:44 - BOS 21:00 2h 16m Direct
      • ORDChicago O'Hare International Airport 17:44
      • BOSBoston Logan International Airport 21:00
      • 2h 16m
      • Direct
      • American Airlines (AA 407)Airbus
      • American Airlines (AA 407)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • Airbus
      • 18:01 ORD
        23:40 BOS
        4Hrs, 39m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 18:01 - BOS 23:40 4h 39m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 18:01
        DCAWashington Ronald Reagan National Airport 22:00
      • DCAWashington Ronald Reagan National Airport 21:00
        BOSBoston Logan International Airport 23:40
      • 4h 39m (1h)
      • 1 Stop DCA · Washington 1h
      • American Airlines (AA 1577)Airbus
        American Airlines (AA 4447)Embraer Emb 175
      • American Airlines (AA 1577)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 18:08 ORD
        23:59 BOS
        4Hrs, 51m 1 Stop (IAD)
      • ORDChicago O'Hare International Airport 18:08 - BOS 23:59 4h 51m 1 Stop (IAD) Washington
      • ORDChicago O'Hare International Airport 18:08
        IADWashington Dulles International Airport 22:24
      • IADWashington Dulles International Airport 21:00
        BOSBoston Logan International Airport 23:59
      • 4h 51m (1h 24m)
      • 1 Stop IAD · Washington 1h 24m
      • United Airlines (UA 444)Boeing 737 800
        United Airlines (UA 755)Airbus
      • United Airlines (UA 444)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 18:08 ORD
        23:59 BOS
        4Hrs, 51m 1 Stop (IAD)
      • ORDChicago O'Hare International Airport 18:08 - BOS 23:59 4h 51m 1 Stop (IAD) Washington
      • ORDChicago O'Hare International Airport 18:08
        IADWashington Dulles International Airport 22:24
      • IADWashington Dulles International Airport 21:00
        BOSBoston Logan International Airport 23:59
      • 4h 51m (1h 24m)
      • 1 Stop IAD · Washington 1h 24m
      • United Airlines (UA 444)Airbus
        United Airlines (UA 755)Boeing 737 Max 8 Passenger
      • United Airlines (UA 444)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 18:08 ORD
        23:59 BOS
        4Hrs, 51m 1 Stop (IAD)
      • ORDChicago O'Hare International Airport 18:08 - BOS 23:59 4h 51m 1 Stop (IAD) Washington
      • ORDChicago O'Hare International Airport 18:08
        IADWashington Dulles International Airport 22:24
      • IADWashington Dulles International Airport 21:00
        BOSBoston Logan International Airport 23:59
      • 4h 51m (1h 24m)
      • 1 Stop IAD · Washington 1h 24m
      • United Airlines (UA 444)Boeing 737 800
        United Airlines (UA 755)Boeing 737 Max 8 Passenger
      • United Airlines (UA 444)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 18:08 ORD
        23:59 BOS
        4Hrs, 51m 1 Stop (IAD)
      • ORDChicago O'Hare International Airport 18:08 - BOS 23:59 4h 51m 1 Stop (IAD) Washington
      • ORDChicago O'Hare International Airport 18:08
        IADWashington Dulles International Airport 22:24
      • IADWashington Dulles International Airport 21:00
        BOSBoston Logan International Airport 23:59
      • 4h 51m (1h 24m)
      • 1 Stop IAD · Washington 1h 24m
      • United Airlines (UA 444)Airbus
        United Airlines (UA 755)Boeing 737 800
      • United Airlines (UA 444)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 18:16 ORD
        23:59 BOS
        4Hrs, 43m 1 Stop (IAD)
      • ORDChicago O'Hare International Airport 18:16 - BOS 23:59 4h 43m 1 Stop (IAD) Washington
      • ORDChicago O'Hare International Airport 18:16
        IADWashington Dulles International Airport 22:22
      • IADWashington Dulles International Airport 21:16
        BOSBoston Logan International Airport 23:59
      • 4h 43m (1h 06m)
      • 1 Stop IAD · Washington 1h 06m
      • United Airlines (UA 2458)Boeing 737 900
        United Airlines (UA 755)Boeing 757 200 Series
      • United Airlines (UA 2458)
        • M
        • T
        • -
        • -
        • -
        • -
        • -
      • 18:16 ORD
        23:59 BOS
        4Hrs, 43m 1 Stop (IAD)
      • ORDChicago O'Hare International Airport 18:16 - BOS 23:59 4h 43m 1 Stop (IAD) Washington
      • ORDChicago O'Hare International Airport 18:16
        IADWashington Dulles International Airport 22:22
      • IADWashington Dulles International Airport 21:16
        BOSBoston Logan International Airport 23:59
      • 4h 43m (1h 06m)
      • 1 Stop IAD · Washington 1h 06m
      • United Airlines (UA 2458)Boeing 737 900
        United Airlines (UA 755)Boeing 737 Max 9 Passenger
      • United Airlines (UA 2458)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 18:30 ORD
        00:38 BOS
        5Hrs, 08m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 18:30 - BOS 00:38 5h 08m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 18:30
        CLTCharlotte Airport 22:29
      • CLTCharlotte Airport 21:55
        BOSBoston Logan International Airport 00:38
      • 5h 08m (34m)
      • 1 Stop CLT · Charlotte 34m
      • American Airlines (AA 689)Boeing 737 800
        American Airlines (AA 1937)Airbus
      • American Airlines (AA 689)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 18:39 ORD
        00:38 BOS
        4Hrs, 59m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 18:39 - BOS 00:38 4h 59m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 18:39
        CLTCharlotte Airport 22:29
      • CLTCharlotte Airport 21:55
        BOSBoston Logan International Airport 00:38
      • 4h 59m (34m)
      • 1 Stop CLT · Charlotte 34m
      • American Airlines (AA 689)Airbus
        American Airlines (AA 1937)Airbus
      • American Airlines (AA 689)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 18:50 MDW
        00:25 BOS
        4Hrs, 35m 1 Stop (BNA)
      • MDWChicago Midway Airport 18:50 - BOS 00:25 4h 35m 1 Stop (BNA)
      • MDWChicago Midway Airport 18:50
        BNANashville Airport 21:00
      • BNANashville Airport 20:15
        BOSBoston Logan International Airport 00:25
      • 4h 35m (45m)
      • 1 Stop BNA · 45m
      • Southwest Airlines (WN 1462)Boeing 737 700
        Southwest Airlines (WN 2456)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1462)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 19:00 MDW
        00:20 BOS
        4Hrs, 20m 1 Stop (STL)
      • MDWChicago Midway Airport 19:00 - BOS 00:20 4h 20m 1 Stop (STL) Saint Louis
      • MDWChicago Midway Airport 19:00
        STLSt Louis Lambert Intl Airport 20:50
      • STLSt Louis Lambert Intl Airport 20:15
        BOSBoston Logan International Airport 00:20
      • 4h 20m (35m)
      • 1 Stop STL · Saint Louis 35m
      • Southwest Airlines (WN 1488)Boeing 737 700
        Southwest Airlines (WN 4422)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1488)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 05:02 ORD
        11:03 BOS
        5Hrs, 01m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:02 - BOS 11:03 5h 01m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:02
        CLTCharlotte Airport 08:55
      • CLTCharlotte Airport 08:08
        BOSBoston Logan International Airport 11:03
      • 5h 01m (47m)
      • 1 Stop CLT · Charlotte 47m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 3040)Boeing 737 800
      • American Airlines (AA 2842)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:10 ORD
        11:05 BOS
        4Hrs, 55m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:10 - BOS 11:05 4h 55m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:10
        CLTCharlotte Airport 08:55
      • CLTCharlotte Airport 08:10
        BOSBoston Logan International Airport 11:05
      • 4h 55m (45m)
      • 1 Stop CLT · Charlotte 45m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 3271)Airbus
      • American Airlines (AA 2842)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:25 MDW
        11:35 BOS
        5Hrs, 10m 1 Stop (BWI)
      • MDWChicago Midway Airport 05:25 - BOS 11:35 5h 10m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 05:25
        BWIBaltimore Washington International Airport 10:05
      • BWIBaltimore Washington International Airport 08:15
        BOSBoston Logan International Airport 11:35
      • 5h 10m (1h 50m)
      • 1 Stop BWI · Baltimore 1h 50m
      • Southwest Airlines (WN 281)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1304)Boeing 737 800
      • Southwest Airlines (WN 281)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 05:45 ORD
        11:25 BOS
        4Hrs, 40m 1 Stop (BWI)
      • ORDChicago O'Hare International Airport 05:45 - BOS 11:25 4h 40m 1 Stop (BWI) Baltimore
      • ORDChicago O'Hare International Airport 05:45
        BWIBaltimore Washington International Airport 09:55
      • BWIBaltimore Washington International Airport 08:40
        BOSBoston Logan International Airport 11:25
      • 4h 40m (1h 15m)
      • 1 Stop BWI · Baltimore 1h 15m
      • Southwest Airlines (WN 1467)Boeing 737 800
        Southwest Airlines (WN 1914)Boeing 737 800
      • Southwest Airlines (WN 1467)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:00 ORD
        12:21 BOS
        5Hrs, 21m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 06:00 - BOS 12:21 5h 21m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 06:00
        DCAWashington Ronald Reagan National Airport 10:40
      • DCAWashington Ronald Reagan National Airport 08:55
        BOSBoston Logan International Airport 12:21
      • 5h 21m (1h 45m)
      • 1 Stop DCA · Washington 1h 45m
      • American Airlines (AA 523)Boeing 737 800
        American Airlines (AA 4635)Embraer Emb 175
      • American Airlines (AA 523)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:00 ORD
        12:11 BOS
        5Hrs, 11m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 06:00 - BOS 12:11 5h 11m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 06:00
        EWRNewark Liberty International Airport 11:00
      • EWRNewark Liberty International Airport 09:11
        BOSBoston Logan International Airport 12:11
      • 5h 11m (1h 49m)
      • 1 Stop EWR · New York City 1h 49m
      • United Airlines (UA 2074)Boeing 757 200 Series
        United Airlines (UA 1864)Boeing 757 200 Series
      • United Airlines (UA 2074)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • 06:00 ORD
        12:41 BOS
        5Hrs, 41m 1 Stop (LGA)
      • ORDChicago O'Hare International Airport 06:00 - BOS 12:41 5h 41m 1 Stop (LGA) New York City
      • ORDChicago O'Hare International Airport 06:00
        LGANew York La Guardia Airport 11:30
      • LGANew York La Guardia Airport 09:04
        BOSBoston Logan International Airport 12:41
      • 5h 41m (2h 26m)
      • 1 Stop LGA · New York City 2h 26m
      • American Airlines (AA 2140)Boeing 737 800
        American Airlines (AA 4450)Embraer Emb 175
      • American Airlines (AA 2140)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 06:00 ORD
        12:11 BOS
        5Hrs, 11m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 06:00 - BOS 12:11 5h 11m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 06:00
        EWRNewark Liberty International Airport 11:00
      • EWRNewark Liberty International Airport 09:11
        BOSBoston Logan International Airport 12:11
      • 5h 11m (1h 49m)
      • 1 Stop EWR · New York City 1h 49m
      • United Airlines (UA 2074)Boeing 737 Max 8 Passenger
        United Airlines (UA 1864)Boeing 757 200 Series
      • United Airlines (UA 2074)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:00 ORD
        12:45 BOS
        5Hrs, 45m 1 Stop (LGA)
      • ORDChicago O'Hare International Airport 06:00 - BOS 12:45 5h 45m 1 Stop (LGA) New York City
      • ORDChicago O'Hare International Airport 06:00
        LGANew York La Guardia Airport 11:34
      • LGANew York La Guardia Airport 09:04
        BOSBoston Logan International Airport 12:45
      • 5h 45m (2h 30m)
      • 1 Stop LGA · New York City 2h 30m
      • American Airlines (AA 2140)Boeing 737 800
        American Airlines (AA 4450)Embraer Emb 175
      • American Airlines (AA 2140)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:00 ORD
        12:27 BOS
        5Hrs, 27m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 06:00 - BOS 12:27 5h 27m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 06:00
        DCAWashington Ronald Reagan National Airport 10:45
      • DCAWashington Ronald Reagan National Airport 08:49
        BOSBoston Logan International Airport 12:27
      • 5h 27m (1h 56m)
      • 1 Stop DCA · Washington 1h 56m
      • American Airlines (AA 523)Boeing 737 800
        American Airlines (AA 2134)Airbus
      • American Airlines (AA 523)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:00 ORD
        12:11 BOS
        5Hrs, 11m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 06:00 - BOS 12:11 5h 11m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 06:00
        EWRNewark Liberty International Airport 11:00
      • EWRNewark Liberty International Airport 09:11
        BOSBoston Logan International Airport 12:11
      • 5h 11m (1h 49m)
      • 1 Stop EWR · New York City 1h 49m
      • United Airlines (UA 2074)Boeing 737 Max 9 Passenger
        United Airlines (UA 1864)Boeing 757 200 Series
      • United Airlines (UA 2074)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 06:00 ORD
        12:06 BOS
        5Hrs, 06m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 06:00 - BOS 12:06 5h 06m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 06:00
        EWRNewark Liberty International Airport 10:55
      • EWRNewark Liberty International Airport 09:10
        BOSBoston Logan International Airport 12:06
      • 5h 06m (1h 45m)
      • 1 Stop EWR · New York City 1h 45m
      • United Airlines (UA 1658)Boeing 757 200 Series
        United Airlines (UA 1864)Boeing 757 200 Series
      • United Airlines (UA 1658)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:05 ORD
        12:07 BOS
        5Hrs, 02m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 06:05 - BOS 12:07 5h 02m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 06:05
        DCAWashington Ronald Reagan National Airport 10:15
      • DCAWashington Ronald Reagan National Airport 09:00
        BOSBoston Logan International Airport 12:07
      • 5h 02m (1h 15m)
      • 1 Stop DCA · Washington 1h 15m
      • American Airlines (AA 523)Boeing 737 800
        American Airlines (AA 4635)Embraer Emb 175
      • American Airlines (AA 523)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:05 ORD
        13:03 BOS
        5Hrs, 58m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 06:05 - BOS 13:03 5h 58m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 06:05
        DCAWashington Ronald Reagan National Airport 11:30
      • DCAWashington Ronald Reagan National Airport 09:00
        BOSBoston Logan International Airport 13:03
      • 5h 58m (2h 30m)
      • 1 Stop DCA · Washington 2h 30m
      • American Airlines (AA 523)Boeing 737 800
        American Airlines (AA 979)Airbus
      • American Airlines (AA 523)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:15 ORD
        12:25 BOS
        5Hrs, 10m 1 Stop (LGA)
      • ORDChicago O'Hare International Airport 06:15 - BOS 12:25 5h 10m 1 Stop (LGA) New York City
      • ORDChicago O'Hare International Airport 06:15
        LGANew York La Guardia Airport 11:12
      • LGANew York La Guardia Airport 09:17
        BOSBoston Logan International Airport 12:25
      • 5h 10m (1h 55m)
      • 1 Stop LGA · New York City 1h 55m
      • American Airlines (AA 3152)Boeing 737 800
        American Airlines (AA 4450)Embraer Emb 175
      • American Airlines (AA 3152)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:25 MDW
        13:10 BOS
        5Hrs, 45m 1 Stop (BNA)
      • MDWChicago Midway Airport 06:25 - BOS 13:10 5h 45m 1 Stop (BNA)
      • MDWChicago Midway Airport 06:25
        BNANashville Airport 09:45
      • BNANashville Airport 08:00
        BOSBoston Logan International Airport 13:10
      • 5h 45m (1h 45m)
      • 1 Stop BNA · 1h 45m
      • Southwest Airlines (WN 6341)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2456)Boeing 737 800
      • Southwest Airlines (WN 6341)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 06:31 ORD
        12:16 BOS
        4Hrs, 45m 1 Stop (PHL)
      • ORDChicago O'Hare International Airport 06:31 - BOS 12:16 4h 45m 1 Stop (PHL) Philadelphia
      • ORDChicago O'Hare International Airport 06:31
        PHLPhiladelphia International Airport 10:50
      • PHLPhiladelphia International Airport 09:32
        BOSBoston Logan International Airport 12:16
      • 4h 45m (1h 18m)
      • 1 Stop PHL · Philadelphia 1h 18m
      • American Airlines (AA 1854)Boeing 737 800
        American Airlines (AA 1416)Boeing 737 800
      • American Airlines (AA 1854)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:31 ORD
        12:20 BOS
        4Hrs, 49m 1 Stop (PHL)
      • ORDChicago O'Hare International Airport 06:31 - BOS 12:20 4h 49m 1 Stop (PHL) Philadelphia
      • ORDChicago O'Hare International Airport 06:31
        PHLPhiladelphia International Airport 10:59
      • PHLPhiladelphia International Airport 09:33
        BOSBoston Logan International Airport 12:20
      • 4h 49m (1h 26m)
      • 1 Stop PHL · Philadelphia 1h 26m
      • American Airlines (AA 1854)Boeing 737 800
        American Airlines (AA 1416)Airbus
      • American Airlines (AA 1854)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 07:00 ORD
        13:57 BOS
        5Hrs, 57m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 07:00 - BOS 13:57 5h 57m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 07:00
        CLTCharlotte Airport 11:30
      • CLTCharlotte Airport 10:01
        BOSBoston Logan International Airport 13:57
      • 5h 57m (1h 29m)
      • 1 Stop CLT · Charlotte 1h 29m
      • American Airlines (AA 1784)Airbus
        American Airlines (AA 3215)Airbus
      • American Airlines (AA 1784)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • 07:00 ORD
        13:33 BOS
        5Hrs, 33m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 07:00 - BOS 13:33 5h 33m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 07:00
        CLTCharlotte Airport 11:19
      • CLTCharlotte Airport 09:58
        BOSBoston Logan International Airport 13:33
      • 5h 33m (1h 21m)
      • 1 Stop CLT · Charlotte 1h 21m
      • American Airlines (AA 1784)Airbus
        American Airlines (AA 3026)Boeing 737 800
      • American Airlines (AA 1784)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:10 ORD
        14:15 BOS
        6Hrs, 05m 1 Stop (EWR)
      • ORDChicago O'Hare International Airport 07:10 - BOS 14:15 6h 05m 1 Stop (EWR) New York City
      • ORDChicago O'Hare International Airport 07:10
        EWRNewark Liberty International Airport 13:00
      • EWRNewark Liberty International Airport 10:27
        BOSBoston Logan International Airport 14:15
      • 6h 05m (2h 33m)
      • 1 Stop EWR · New York City 2h 33m
      • United Airlines (UA 563)Boeing 757 200 Series
        United Airlines (UA 3492)Embraer 175
      • United Airlines (UA 563)
        • -
        • -
        • -
        • T
        • F
        • S
        • S
      • 07:15 MDW
        13:00 BOS
        4Hrs, 45m 1 Stop (STL)
      • MDWChicago Midway Airport 07:15 - BOS 13:00 4h 45m 1 Stop (STL) Saint Louis
      • MDWChicago Midway Airport 07:15
        STLSt Louis Lambert Intl Airport 09:30
      • STLSt Louis Lambert Intl Airport 08:35
        BOSBoston Logan International Airport 13:00
      • 4h 45m (55m)
      • 1 Stop STL · Saint Louis 55m
      • Southwest Airlines (WN 794)Boeing 737 700
        Southwest Airlines (WN 2357)Boeing 737 800
      • Southwest Airlines (WN 794)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:19 ORD
        12:25 BOS
        4Hrs, 06m 1 Stop (LGA)
      • ORDChicago O'Hare International Airport 07:19 - BOS 12:25 4h 06m 1 Stop (LGA) New York City
      • ORDChicago O'Hare International Airport 07:19
        LGANew York La Guardia Airport 11:12
      • LGANew York La Guardia Airport 10:23
        BOSBoston Logan International Airport 12:25
      • 4h 06m (49m)
      • 1 Stop LGA · New York City 49m
      • American Airlines (AA 1642)Boeing 737 800
        American Airlines (AA 4450)Embraer Emb 175
      • American Airlines (AA 1642)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:24 ORD
        12:41 BOS
        4Hrs, 17m 1 Stop (LGA)
      • ORDChicago O'Hare International Airport 07:24 - BOS 12:41 4h 17m 1 Stop (LGA) New York City
      • ORDChicago O'Hare International Airport 07:24
        LGANew York La Guardia Airport 11:30
      • LGANew York La Guardia Airport 10:33
        BOSBoston Logan International Airport 12:41
      • 4h 17m (57m)
      • 1 Stop LGA · New York City 57m
      • American Airlines (AA 3270)Boeing 737 800
        American Airlines (AA 4450)Embraer Emb 175
      • American Airlines (AA 3270)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 07:24 ORD
        12:45 BOS
        4Hrs, 21m 1 Stop (LGA)
      • ORDChicago O'Hare International Airport 07:24 - BOS 12:45 4h 21m 1 Stop (LGA) New York City
      • ORDChicago O'Hare International Airport 07:24
        LGANew York La Guardia Airport 11:34
      • LGANew York La Guardia Airport 10:33
        BOSBoston Logan International Airport 12:45
      • 4h 21m (1h 01m)
      • 1 Stop LGA · New York City 1h 01m
      • American Airlines (AA 3270)Boeing 737 800
        American Airlines (AA 4450)Embraer Emb 175
      • American Airlines (AA 3270)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 07:25 MDW
        13:50 BOS
        5Hrs, 25m 1 Stop (BWI)
      • MDWChicago Midway Airport 07:25 - BOS 13:50 5h 25m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 07:25
        BWIBaltimore Washington International Airport 12:25
      • BWIBaltimore Washington International Airport 10:15
        BOSBoston Logan International Airport 13:50
      • 5h 25m (2h 10m)
      • 1 Stop BWI · Baltimore 2h 10m
      • Southwest Airlines (WN 3286)Boeing 737 700
        Southwest Airlines (WN 5222)Boeing 737 800
      • Southwest Airlines (WN 3286)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:35 MDW
        13:10 BOS
        4Hrs, 35m 1 Stop (BNA)
      • MDWChicago Midway Airport 07:35 - BOS 13:10 4h 35m 1 Stop (BNA)
      • MDWChicago Midway Airport 07:35
        BNANashville Airport 09:45
      • BNANashville Airport 09:05
        BOSBoston Logan International Airport 13:10
      • 4h 35m (40m)
      • 1 Stop BNA · 40m
      • Southwest Airlines (WN 4390)Boeing 737 700
        Southwest Airlines (WN 1828)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4390)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 08:00 ORD
        13:57 BOS
        4Hrs, 57m 1 Stop (SYR)
      • ORDChicago O'Hare International Airport 08:00 - BOS 13:57 4h 57m 1 Stop (SYR) Syracuse
      • ORDChicago O'Hare International Airport 08:00
        SYRSyracuse Airport 12:24
      • SYRSyracuse Airport 10:57
        BOSBoston Logan International Airport 13:57
      • 4h 57m (1h 27m)
      • 1 Stop SYR · Syracuse 1h 27m
      • American Airlines (AA 4134)Embraer 170
        American Airlines (AA 5873)Er4 Embraer Rj145 Amazon
      • American Airlines (AA 4134)
        • M
        • T
        • W
        • -
        • -
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        • -
      • 08:05 ORD
        13:03 BOS
        3Hrs, 58m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 08:05 - BOS 13:03 3h 58m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 08:05
        DCAWashington Ronald Reagan National Airport 11:30
      • DCAWashington Ronald Reagan National Airport 10:59
        BOSBoston Logan International Airport 13:03
      • 3h 58m (31m)
      • 1 Stop DCA · Washington 31m
      • American Airlines (AA 2345)Boeing 737 800
        American Airlines (AA 979)Airbus
      • American Airlines (AA 2345)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 08:05 ORD
        15:07 BOS
        6Hrs, 02m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 08:05 - BOS 15:07 6h 02m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 08:05
        DCAWashington Ronald Reagan National Airport 13:33
      • DCAWashington Ronald Reagan National Airport 10:55
        BOSBoston Logan International Airport 15:07
      • 6h 02m (2h 38m)
      • 1 Stop DCA · Washington 2h 38m
      • American Airlines (AA 2345)Boeing 737 800
        American Airlines (AA 4460)Embraer Emb 175
      • American Airlines (AA 2345)
        • M
        • T
        • W
        • -
        • -
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        • -
      • 08:05 ORD
        15:02 BOS
        5Hrs, 57m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 08:05 - BOS 15:02 5h 57m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 08:05
        DCAWashington Ronald Reagan National Airport 13:25
      • DCAWashington Ronald Reagan National Airport 10:59
        BOSBoston Logan International Airport 15:02
      • 5h 57m (2h 26m)
      • 1 Stop DCA · Washington 2h 26m
      • American Airlines (AA 2345)Boeing 737 800
        American Airlines (AA 4404)Embraer Emb 175
      • American Airlines (AA 2345)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 08:15 MDW
        15:25 BOS
        6Hrs, 10m 1 Stop (BWI)
      • MDWChicago Midway Airport 08:15 - BOS 15:25 6h 10m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 08:15
        BWIBaltimore Washington International Airport 14:00
      • BWIBaltimore Washington International Airport 11:05
        BOSBoston Logan International Airport 15:25
      • 6h 10m (2h 55m)
      • 1 Stop BWI · Baltimore 2h 55m
      • Southwest Airlines (WN 4325)Boeing 737 700
        Southwest Airlines (WN 2986)Boeing 737 800
      • Southwest Airlines (WN 4325)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 08:15 MDW
        14:40 BOS
        5Hrs, 25m 1 Stop (BWI)
      • MDWChicago Midway Airport 08:15 - BOS 14:40 5h 25m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 08:15
        BWIBaltimore Washington International Airport 13:15
      • BWIBaltimore Washington International Airport 11:05
        BOSBoston Logan International Airport 14:40
      • 5h 25m (2h 10m)
      • 1 Stop BWI · Baltimore 2h 10m
      • Southwest Airlines (WN 4633)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 954)Boeing 737 700
      • Southwest Airlines (WN 4633)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 08:20 ORD
        13:53 BOS
        4Hrs, 33m 1 Stop (SYR)
      • ORDChicago O'Hare International Airport 08:20 - BOS 13:53 4h 33m 1 Stop (SYR) Syracuse
      • ORDChicago O'Hare International Airport 08:20
        SYRSyracuse Airport 12:29
      • SYRSyracuse Airport 11:24
        BOSBoston Logan International Airport 13:53
      • 4h 33m (1h 05m)
      • 1 Stop SYR · Syracuse 1h 05m
      • American Airlines (AA 4134)Embraer 170
        American Airlines (AA 5873)Er4 Embraer Rj145 Amazon
      • American Airlines (AA 4134)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 08:30 ORD
        15:36 BOS
        6Hrs, 06m 1 Stop (CVG)
      • ORDChicago O'Hare International Airport 08:30 - BOS 15:36 6h 06m 1 Stop (CVG) Cincinnati
      • ORDChicago O'Hare International Airport 08:30
        CVGCincinnati Northern Kentucky Intl Airport 13:31
      • CVGCincinnati Northern Kentucky Intl Airport 10:52
        BOSBoston Logan International Airport 15:36
      • 6h 06m (2h 39m)
      • 1 Stop CVG · Cincinnati 2h 39m
      • American Airlines (AA 6043)Crj Canadair Regional
        American Airlines (AA 3593)Embraer Emb 175
      • American Airlines (AA 6043)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 08:45 ORD
        14:26 BOS
        4Hrs, 41m 1 Stop (IAD)
      • ORDChicago O'Hare International Airport 08:45 - BOS 14:26 4h 41m 1 Stop (IAD) Washington
      • ORDChicago O'Hare International Airport 08:45
        IADWashington Dulles International Airport 12:50
      • IADWashington Dulles International Airport 11:43
        BOSBoston Logan International Airport 14:26
      • 4h 41m (1h 07m)
      • 1 Stop IAD · Washington 1h 07m
      • United Airlines (UA 545)Airbus
        United Airlines (UA 2060)Airbus
      • United Airlines (UA 545)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 08:48 ORD
        14:32 BOS
        4Hrs, 44m 1 Stop (IAD)
      • ORDChicago O'Hare International Airport 08:48 - BOS 14:32 4h 44m 1 Stop (IAD) Washington
      • ORDChicago O'Hare International Airport 08:48
        IADWashington Dulles International Airport 12:55
      • IADWashington Dulles International Airport 11:44
        BOSBoston Logan International Airport 14:32
      • 4h 44m (1h 11m)
      • 1 Stop IAD · Washington 1h 11m
      • United Airlines (UA 2415)Boeing 737 800
        United Airlines (UA 2060)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2415)
        • M
        • T
        • W
        • -
        • -
        • -
        • -
      • 08:48 ORD
        13:53 BOS
        4Hrs, 05m 1 Stop (SYR)
      • ORDChicago O'Hare International Airport 08:48 - BOS 13:53 4h 05m 1 Stop (SYR) Syracuse
      • ORDChicago O'Hare International Airport 08:48
        SYRSyracuse Airport 12:29
      • SYRSyracuse Airport 11:54
        BOSBoston Logan International Airport 13:53
      • 4h 05m (35m)
      • 1 Stop SYR · Syracuse 35m
      • American Airlines (AA 4134)Embraer 170
        American Airlines (AA 5873)Er4 Embraer Rj145 Amazon
      • American Airlines (AA 4134)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 08:50 ORD
        14:26 BOS
        4Hrs, 36m 1 Stop (IAD)
      • ORDChicago O'Hare International Airport 08:50 - BOS 14:26 4h 36m 1 Stop (IAD) Washington
      • ORDChicago O'Hare International Airport 08:50
        IADWashington Dulles International Airport 12:50
      • IADWashington Dulles International Airport 11:48
        BOSBoston Logan International Airport 14:26
      • 4h 36m (1h 02m)
      • 1 Stop IAD · Washington 1h 02m
      • United Airlines (UA 545)Airbus
        United Airlines (UA 2060)Airbus
      • United Airlines (UA 545)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
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      What’s the fastest flight time from Chicago to Boston?

      The fastest flight time for direct flights from Chicago to Boston is 2 hours 10 minutes. Check latest flight schedules & prices on Wego.

      What’s the most popular airline flying from Chicago to Boston?

      The most popular airline flying from Chicago to Boston is Frontier Airlines. Find the latest flight deals on Wego.

      How far is Boston from Chicago?

      The flight distance between Chicago and Boston is 1366km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 05:02. The last flight of the day departs at 18:01. See the full list of flight times on Wego.

      How many airlines offer direct flights from Chicago to Boston?

      There are 4 airlines that offer direct flights from Chicago to Boston. Find out the list of airlines on Wego.

      All Airports in Boston

      Boston Logan International Airport BOS

      Popular Airlines Flying From Chicago to Boston

      Frontier Airlines ‏()
      United Airlines ‏()

      Popular Destinations From Boston

      Popular Destinations From Chicago

      Popular Hotels in Boston

      Hotels In Popular Destinations