Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Frontier Airlines

The cheapest airline(s) flying from San Antonio to Chicago is Frontier Airlines.

  • Frontier Airlines Frontier Airlines
  • Spirit Airlines Spirit Airlines
  • United Airlines United Airlines
  • American Airlines American Airlines
  • Southwest Airlines Southwest Airlines
  • Alaska Airlines Alaska Airlines
Cheapest Month April

Travel Period: December 2024 - November 2025

The cheapest month(s) to fly from San Antonio to Chicago is April.

  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
Cheapest Day of the Week Wednesday

The cheapest day(s) of the week to fly from San Antonio to Chicago is Wednesday.

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

Flight Schedules

Last Updated: Sat, 2 Nov, 2024

  • Time Earliest
    • Earliest
    • Latest
  • Depart Earliest
    • Earliest
    • Latest
  • Arrive
    • Earliest
    • Latest
  • Duration
    • Shortest
    • Longest
  • Stopover
    All
    • Airline Filter by Airline
      View All Airline
      • Availability
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 05:45 SAT
        08:15 MDW
        2Hrs, 30m Direct
      • SATSan Antonio International Airport 05:45 - MDW 08:15 2h 30m Direct
      • SATSan Antonio International Airport 05:45
      • MDWChicago Midway Airport 08:15
      • 2h 30m
      • Direct
      • Southwest Airlines (WN 2243)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2243)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 06:10 SAT
        08:58 ORD
        2Hrs, 48m Direct
      • SATSan Antonio International Airport 06:10 - ORD 08:58 2h 48m Direct
      • SATSan Antonio International Airport 06:10
      • ORDChicago O'Hare International Airport 08:58
      • 2h 48m
      • Direct
      • American Airlines (AA 671)Boeing 737 800
      • American Airlines (AA 671)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 06:50 SAT
        09:25 MDW
        2Hrs, 35m Direct
      • SATSan Antonio International Airport 06:50 - MDW 09:25 2h 35m Direct
      • SATSan Antonio International Airport 06:50
      • MDWChicago Midway Airport 09:25
      • 2h 35m
      • Direct
      • Southwest Airlines (WN 2176)Boeing 737 700
      • Southwest Airlines (WN 2176)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 700
      • 07:00 SAT
        09:48 ORD
        2Hrs, 48m Direct
      • SATSan Antonio International Airport 07:00 - ORD 09:48 2h 48m Direct
      • SATSan Antonio International Airport 07:00
      • ORDChicago O'Hare International Airport 09:48
      • 2h 48m
      • Direct
      • United Airlines (UA 2067)Boeing 737 700
      • United Airlines (UA 2067)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 700
      • 08:10 SAT
        10:40 MDW
        2Hrs, 30m Direct
      • SATSan Antonio International Airport 08:10 - MDW 10:40 2h 30m Direct
      • SATSan Antonio International Airport 08:10
      • MDWChicago Midway Airport 10:40
      • 2h 30m
      • Direct
      • Southwest Airlines (WN 2243)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2243)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 08:49 SAT
        14:46 ORD
        5Hrs, 57m Direct
      • SATSan Antonio International Airport 08:49 - ORD 14:46 5h 57m Direct
      • SATSan Antonio International Airport 08:49
      • ORDChicago O'Hare International Airport 14:46
      • 5h 57m
      • Direct
      • United Airlines (UA 2312)Boeing 737 800
      • United Airlines (UA 2312)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 13:54 SAT
        16:45 ORD
        2Hrs, 51m Direct
      • SATSan Antonio International Airport 13:54 - ORD 16:45 2h 51m Direct
      • SATSan Antonio International Airport 13:54
      • ORDChicago O'Hare International Airport 16:45
      • 2h 51m
      • Direct
      • American Airlines (AA 1112)Boeing 737 800
      • American Airlines (AA 1112)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 14:13 SAT
        17:01 ORD
        2Hrs, 48m Direct
      • SATSan Antonio International Airport 14:13 - ORD 17:01 2h 48m Direct
      • SATSan Antonio International Airport 14:13
      • ORDChicago O'Hare International Airport 17:01
      • 2h 48m
      • Direct
      • United Airlines (UA 2243)Boeing 737 900
      • United Airlines (UA 2243)
        • M
        • -
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 900
      • 14:13 SAT
        17:01 ORD
        2Hrs, 48m Direct
      • SATSan Antonio International Airport 14:13 - ORD 17:01 2h 48m Direct
      • SATSan Antonio International Airport 14:13
      • ORDChicago O'Hare International Airport 17:01
      • 2h 48m
      • Direct
      • United Airlines (UA 2243)Boeing 737 800
      • United Airlines (UA 2243)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 14:55 SAT
        17:25 MDW
        2Hrs, 30m Direct
      • SATSan Antonio International Airport 14:55 - MDW 17:25 2h 30m Direct
      • SATSan Antonio International Airport 14:55
      • MDWChicago Midway Airport 17:25
      • 2h 30m
      • Direct
      • Southwest Airlines (WN 2039)Boeing 737 800
      • Southwest Airlines (WN 2039)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 15:54 SAT
        18:45 ORD
        2Hrs, 51m Direct
      • SATSan Antonio International Airport 15:54 - ORD 18:45 2h 51m Direct
      • SATSan Antonio International Airport 15:54
      • ORDChicago O'Hare International Airport 18:45
      • 2h 51m
      • Direct
      • American Airlines (AA 1112)Boeing 737 800
      • American Airlines (AA 1112)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 800
      • 16:55 SAT
        19:30 MDW
        2Hrs, 35m Direct
      • SATSan Antonio International Airport 16:55 - MDW 19:30 2h 35m Direct
      • SATSan Antonio International Airport 16:55
      • MDWChicago Midway Airport 19:30
      • 2h 35m
      • Direct
      • Southwest Airlines (WN 2039)Boeing 737 800
      • Southwest Airlines (WN 2039)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • Boeing 737 800
      • 18:20 SAT
        22:30 MDW
        4Hrs, 10m 1 Stop (HOU)
      • SATSan Antonio International Airport 18:20 - MDW 22:30 4h 10m 1 Stop (HOU) Houston
      • SATSan Antonio International Airport 18:20
        HOUHouston Hobby Airport 20:10
      • HOUHouston Hobby Airport 19:20
        MDWChicago Midway Airport 22:30
      • 4h 10m (50m)
      • 1 Stop HOU · Houston 50m
      • Southwest Airlines (WN 1816)Boeing 737 700
        Southwest Airlines (WN 1732)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1816)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 18:25 SAT
        23:10 MDW
        4Hrs, 45m 1 Stop (ATL)
      • SATSan Antonio International Airport 18:25 - MDW 23:10 4h 45m 1 Stop (ATL) Atlanta
      • SATSan Antonio International Airport 18:25
        ATLAtlanta Hartsfield-Jackson Intl Airport 22:15
      • ATLAtlanta Hartsfield-Jackson Intl Airport 21:35
        MDWChicago Midway Airport 23:10
      • 4h 45m (40m)
      • 1 Stop ATL · Atlanta 40m
      • Southwest Airlines (WN 3304)Boeing 737 700
        Southwest Airlines (WN 4703)Boeing 737 800
      • Southwest Airlines (WN 3304)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 18:40 SAT
        23:49 ORD
        5Hrs, 09m 1 Stop (DFW)
      • SATSan Antonio International Airport 18:40 - ORD 23:49 5h 09m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 18:40
        DFWDallas/Fort Worth Intl Airport 21:25
      • DFWDallas/Fort Worth Intl Airport 20:00
        ORDChicago O'Hare International Airport 23:49
      • 5h 09m (1h 25m)
      • 1 Stop DFW · Dallas 1h 25m
      • American Airlines (AA 1101)Airbus
        American Airlines (AA 2881)Boeing 737 800
      • American Airlines (AA 1101)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 18:45 SAT
        23:49 ORD
        5Hrs, 04m 1 Stop (DFW)
      • SATSan Antonio International Airport 18:45 - ORD 23:49 5h 04m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 18:45
        DFWDallas/Fort Worth Intl Airport 21:25
      • DFWDallas/Fort Worth Intl Airport 20:05
        ORDChicago O'Hare International Airport 23:49
      • 5h 04m (1h 20m)
      • 1 Stop DFW · Dallas 1h 20m
      • American Airlines (AA 1101)Airbus
        American Airlines (AA 2881)Boeing 737 800
      • American Airlines (AA 1101)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 18:45 SAT
        23:51 ORD
        5Hrs, 06m 1 Stop (DFW)
      • SATSan Antonio International Airport 18:45 - ORD 23:51 5h 06m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 18:45
        DFWDallas/Fort Worth Intl Airport 21:25
      • DFWDallas/Fort Worth Intl Airport 20:05
        ORDChicago O'Hare International Airport 23:51
      • 5h 06m (1h 20m)
      • 1 Stop DFW · Dallas 1h 20m
      • American Airlines (AA 1101)Airbus
        American Airlines (AA 2881)Boeing 737 800
      • American Airlines (AA 1101)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 18:50 SAT
        22:50 MDW
        4Hrs, 00m 1 Stop (DAL)
      • SATSan Antonio International Airport 18:50 - MDW 22:50 4h 1 Stop (DAL)
      • SATSan Antonio International Airport 18:50
        DALDallas/Fort Worth Love Field Airport 20:40
      • DALDallas/Fort Worth Love Field Airport 19:55
        MDWChicago Midway Airport 22:50
      • 4h (45m)
      • 1 Stop DAL · 45m
      • Southwest Airlines (WN 3226)Boeing 737 800
        Southwest Airlines (WN 4821)Boeing 737 800
      • Southwest Airlines (WN 3226)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 18:50 SAT
        00:50 MDW
        6Hrs, 00m 1 Stop (DAL)
      • SATSan Antonio International Airport 18:50 - MDW 00:50 6h 1 Stop (DAL)
      • SATSan Antonio International Airport 18:50
        DALDallas/Fort Worth Love Field Airport 22:45
      • DALDallas/Fort Worth Love Field Airport 19:55
        MDWChicago Midway Airport 00:50
      • 6h (2h 50m)
      • 1 Stop DAL · 2h 50m
      • Southwest Airlines (WN 3226)Boeing 737 800
        Southwest Airlines (WN 5269)Boeing 737 700
      • Southwest Airlines (WN 3226)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 18:52 SAT
        01:33 MDW
        6Hrs, 41m 1 Stop (DEN)
      • SATSan Antonio International Airport 18:52 - MDW 01:33 6h 41m 1 Stop (DEN) Denver
      • SATSan Antonio International Airport 18:52
        DENDenver Intl Airport 22:11
      • DENDenver Intl Airport 20:15
        MDWChicago Midway Airport 01:33
      • 6h 41m (1h 56m)
      • 1 Stop DEN · Denver 1h 56m
      • Frontier Airlines (F9 2355)Airbus A320 Neo
        Frontier Airlines (F9 2946)Airbus A320 Neo
      • Frontier Airlines (F9 2355)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 18:56 SAT
        23:59 ORD
        5Hrs, 03m 1 Stop (IAH)
      • SATSan Antonio International Airport 18:56 - ORD 23:59 5h 03m 1 Stop (IAH) Houston
      • SATSan Antonio International Airport 18:56
        IAHHouston George Bush Intercontinental Airport 21:30
      • IAHHouston George Bush Intercontinental Airport 20:05
        ORDChicago O'Hare International Airport 23:59
      • 5h 03m (1h 25m)
      • 1 Stop IAH · Houston 1h 25m
      • United Airlines (UA 5895)Embraer 175
        United Airlines (UA 556)Boeing 737 900
      • United Airlines (UA 5895)
        • M
        • T
        • W
        • T
        • F
        • -
        • -
      • 18:56 SAT
        23:59 ORD
        5Hrs, 03m 1 Stop (IAH)
      • SATSan Antonio International Airport 18:56 - ORD 23:59 5h 03m 1 Stop (IAH) Houston
      • SATSan Antonio International Airport 18:56
        IAHHouston George Bush Intercontinental Airport 21:30
      • IAHHouston George Bush Intercontinental Airport 20:05
        ORDChicago O'Hare International Airport 23:59
      • 5h 03m (1h 25m)
      • 1 Stop IAH · Houston 1h 25m
      • United Airlines (UA 6158)Embraer 175
        United Airlines (UA 556)Boeing 737 900
      • United Airlines (UA 6158)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 20:55 SAT
        00:50 MDW
        3Hrs, 55m 1 Stop (DAL)
      • SATSan Antonio International Airport 20:55 - MDW 00:50 3h 55m 1 Stop (DAL)
      • SATSan Antonio International Airport 20:55
        DALDallas/Fort Worth Love Field Airport 22:45
      • DALDallas/Fort Worth Love Field Airport 22:00
        MDWChicago Midway Airport 00:50
      • 3h 55m (45m)
      • 1 Stop DAL · 45m
      • Southwest Airlines (WN 4807)Boeing 737 700
        Southwest Airlines (WN 5269)Boeing 737 700
      • Southwest Airlines (WN 4807)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:00 SAT
        09:25 ORD
        4Hrs, 25m 1 Stop (DFW)
      • SATSan Antonio International Airport 05:00 - ORD 09:25 4h 25m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 07:00
      • DFWDallas/Fort Worth Intl Airport 06:15
        ORDChicago O'Hare International Airport 09:25
      • 4h 25m (45m)
      • 1 Stop DFW · Dallas 45m
      • American Airlines (AA 2616)Airbus
        American Airlines (AA 1106)Boeing 737 800
      • American Airlines (AA 2616)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:00 SAT
        09:27 ORD
        4Hrs, 27m 1 Stop (DFW)
      • SATSan Antonio International Airport 05:00 - ORD 09:27 4h 27m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 07:00
      • DFWDallas/Fort Worth Intl Airport 06:15
        ORDChicago O'Hare International Airport 09:27
      • 4h 27m (45m)
      • 1 Stop DFW · Dallas 45m
      • American Airlines (AA 2616)Airbus
        American Airlines (AA 1106)Boeing 737 800
      • American Airlines (AA 2616)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 05:00 SAT
        09:27 ORD
        4Hrs, 27m 1 Stop (DFW)
      • SATSan Antonio International Airport 05:00 - ORD 09:27 4h 27m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 07:00
      • DFWDallas/Fort Worth Intl Airport 06:14
        ORDChicago O'Hare International Airport 09:27
      • 4h 27m (46m)
      • 1 Stop DFW · Dallas 46m
      • American Airlines (AA 2616)Airbus
        American Airlines (AA 1106)Boeing 737 800
      • American Airlines (AA 2616)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:00 SAT
        10:02 ORD
        5Hrs, 02m 1 Stop (IAH)
      • SATSan Antonio International Airport 05:00 - ORD 10:02 5h 02m 1 Stop (IAH) Houston
      • SATSan Antonio International Airport 05:00
        IAHHouston George Bush Intercontinental Airport 07:20
      • IAHHouston George Bush Intercontinental Airport 06:09
        ORDChicago O'Hare International Airport 10:02
      • 5h 02m (1h 11m)
      • 1 Stop IAH · Houston 1h 11m
      • United Airlines (UA 5463)Embraer 175
        United Airlines (UA 469)Boeing 737 Max 8 Passenger
      • United Airlines (UA 5463)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 05:00 SAT
        10:02 ORD
        5Hrs, 02m 1 Stop (IAH)
      • SATSan Antonio International Airport 05:00 - ORD 10:02 5h 02m 1 Stop (IAH) Houston
      • SATSan Antonio International Airport 05:00
        IAHHouston George Bush Intercontinental Airport 07:20
      • IAHHouston George Bush Intercontinental Airport 06:06
        ORDChicago O'Hare International Airport 10:02
      • 5h 02m (1h 14m)
      • 1 Stop IAH · Houston 1h 14m
      • United Airlines (UA 744)Boeing 737 800
        United Airlines (UA 469)Airbus A321 Neo
      • United Airlines (UA 744)
        • -
        • -
        • -
        • T
        • -
        • -
        • S
      • 05:00 SAT
        10:02 ORD
        5Hrs, 02m 1 Stop (IAH)
      • SATSan Antonio International Airport 05:00 - ORD 10:02 5h 02m 1 Stop (IAH) Houston
      • SATSan Antonio International Airport 05:00
        IAHHouston George Bush Intercontinental Airport 07:20
      • IAHHouston George Bush Intercontinental Airport 06:06
        ORDChicago O'Hare International Airport 10:02
      • 5h 02m (1h 14m)
      • 1 Stop IAH · Houston 1h 14m
      • United Airlines (UA 744)Airbus
        United Airlines (UA 469)Airbus A321 Neo
      • United Airlines (UA 744)
        • M
        • T
        • -
        • -
        • -
        • S
        • -
      • 05:00 SAT
        10:02 ORD
        5Hrs, 02m 1 Stop (IAH)
      • SATSan Antonio International Airport 05:00 - ORD 10:02 5h 02m 1 Stop (IAH) Houston
      • SATSan Antonio International Airport 05:00
        IAHHouston George Bush Intercontinental Airport 07:20
      • IAHHouston George Bush Intercontinental Airport 06:06
        ORDChicago O'Hare International Airport 10:02
      • 5h 02m (1h 14m)
      • 1 Stop IAH · Houston 1h 14m
      • United Airlines (UA 744)Airbus
        United Airlines (UA 469)Boeing 737 Max 8 Passenger
      • United Airlines (UA 744)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 05:00 SAT
        10:56 ORD
        5Hrs, 56m 1 Stop (DFW)
      • SATSan Antonio International Airport 05:00 - ORD 10:56 5h 56m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 08:35
      • DFWDallas/Fort Worth Intl Airport 06:15
        ORDChicago O'Hare International Airport 10:56
      • 5h 56m (2h 20m)
      • 1 Stop DFW · Dallas 2h 20m
      • American Airlines (AA 2616)Airbus
        American Airlines (AA 328)Airbus
      • American Airlines (AA 2616)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:00 SAT
        10:58 ORD
        5Hrs, 58m 1 Stop (DFW)
      • SATSan Antonio International Airport 05:00 - ORD 10:58 5h 58m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 08:35
      • DFWDallas/Fort Worth Intl Airport 06:14
        ORDChicago O'Hare International Airport 10:58
      • 5h 58m (2h 21m)
      • 1 Stop DFW · Dallas 2h 21m
      • American Airlines (AA 2616)Airbus
        American Airlines (AA 328)Airbus
      • American Airlines (AA 2616)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:00 SAT
        10:58 ORD
        5Hrs, 58m 1 Stop (DFW)
      • SATSan Antonio International Airport 05:00 - ORD 10:58 5h 58m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 08:35
      • DFWDallas/Fort Worth Intl Airport 06:15
        ORDChicago O'Hare International Airport 10:58
      • 5h 58m (2h 20m)
      • 1 Stop DFW · Dallas 2h 20m
      • American Airlines (AA 2616)Airbus
        American Airlines (AA 328)Airbus
      • American Airlines (AA 2616)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 05:00 SAT
        11:12 ORD
        6Hrs, 12m 1 Stop (IAH)
      • SATSan Antonio International Airport 05:00 - ORD 11:12 6h 12m 1 Stop (IAH) Houston
      • SATSan Antonio International Airport 05:00
        IAHHouston George Bush Intercontinental Airport 08:30
      • IAHHouston George Bush Intercontinental Airport 06:06
        ORDChicago O'Hare International Airport 11:12
      • 6h 12m (2h 24m)
      • 1 Stop IAH · Houston 2h 24m
      • United Airlines (UA 744)Airbus
        United Airlines (UA 1544)Boeing 737 900
      • United Airlines (UA 744)
        • M
        • T
        • -
        • -
        • F
        • S
        • -
      • 05:00 SAT
        11:12 ORD
        6Hrs, 12m 1 Stop (IAH)
      • SATSan Antonio International Airport 05:00 - ORD 11:12 6h 12m 1 Stop (IAH) Houston
      • SATSan Antonio International Airport 05:00
        IAHHouston George Bush Intercontinental Airport 08:30
      • IAHHouston George Bush Intercontinental Airport 06:09
        ORDChicago O'Hare International Airport 11:12
      • 6h 12m (2h 21m)
      • 1 Stop IAH · Houston 2h 21m
      • United Airlines (UA 5463)Embraer 175
        United Airlines (UA 1544)Boeing 737 900
      • United Airlines (UA 5463)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 05:00 SAT
        11:12 ORD
        6Hrs, 12m 1 Stop (IAH)
      • SATSan Antonio International Airport 05:00 - ORD 11:12 6h 12m 1 Stop (IAH) Houston
      • SATSan Antonio International Airport 05:00
        IAHHouston George Bush Intercontinental Airport 08:30
      • IAHHouston George Bush Intercontinental Airport 06:06
        ORDChicago O'Hare International Airport 11:12
      • 6h 12m (2h 24m)
      • 1 Stop IAH · Houston 2h 24m
      • United Airlines (UA 744)Boeing 737 800
        United Airlines (UA 1544)Boeing 737 900
      • United Airlines (UA 744)
        • -
        • -
        • -
        • T
        • -
        • -
        • S
      • 05:20 SAT
        09:30 MDW
        4Hrs, 10m 1 Stop (DAL)
      • SATSan Antonio International Airport 05:20 - MDW 09:30 4h 10m 1 Stop (DAL)
      • SATSan Antonio International Airport 05:20
        DALDallas/Fort Worth Love Field Airport 07:20
      • DALDallas/Fort Worth Love Field Airport 06:30
        MDWChicago Midway Airport 09:30
      • 4h 10m (50m)
      • 1 Stop DAL · 50m
      • Southwest Airlines (WN 294)Boeing 737 800
        Southwest Airlines (WN 938)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 294)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:30 SAT
        11:20 ORD
        5Hrs, 50m 1 Stop (DEN)
      • SATSan Antonio International Airport 05:30 - ORD 11:20 5h 50m 1 Stop (DEN) Denver
      • SATSan Antonio International Airport 05:30
        DENDenver Intl Airport 07:49
      • DENDenver Intl Airport 06:53
        ORDChicago O'Hare International Airport 11:20
      • 5h 50m (56m)
      • 1 Stop DEN · Denver 56m
      • United Airlines (UA 1481)Airbus
        United Airlines (UA 288)Boeing 777
      • United Airlines (UA 1481)
        • M
        • T
        • W
        • T
        • F
        • S
        • -
      • 05:30 SAT
        11:20 ORD
        5Hrs, 50m 1 Stop (DEN)
      • SATSan Antonio International Airport 05:30 - ORD 11:20 5h 50m 1 Stop (DEN) Denver
      • SATSan Antonio International Airport 05:30
        DENDenver Intl Airport 07:49
      • DENDenver Intl Airport 06:53
        ORDChicago O'Hare International Airport 11:20
      • 5h 50m (56m)
      • 1 Stop DEN · Denver 56m
      • United Airlines (UA 1481)Boeing 737 800
        United Airlines (UA 288)Boeing 777
      • United Airlines (UA 1481)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 06:00 SAT
        10:40 MDW
        4Hrs, 40m 1 Stop (DAL)
      • SATSan Antonio International Airport 06:00 - MDW 10:40 4h 40m 1 Stop (DAL)
      • SATSan Antonio International Airport 06:00
        DALDallas/Fort Worth Love Field Airport 08:30
      • DALDallas/Fort Worth Love Field Airport 07:10
        MDWChicago Midway Airport 10:40
      • 4h 40m (1h 20m)
      • 1 Stop DAL · 1h 20m
      • Southwest Airlines (WN 294)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 4696)Boeing 737 800
      • Southwest Airlines (WN 294)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:00 SAT
        11:30 ORD
        5Hrs, 30m 1 Stop (DAL)
      • SATSan Antonio International Airport 06:00 - ORD 11:30 5h 30m 1 Stop (DAL)
      • SATSan Antonio International Airport 06:00
        DALDallas/Fort Worth Love Field Airport 09:05
      • DALDallas/Fort Worth Love Field Airport 07:10
        ORDChicago O'Hare International Airport 11:30
      • 5h 30m (1h 55m)
      • 1 Stop DAL · 1h 55m
      • Southwest Airlines (WN 294)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 4429)Boeing 737 800
      • Southwest Airlines (WN 294)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:01 SAT
        10:56 ORD
        4Hrs, 55m 1 Stop (DFW)
      • SATSan Antonio International Airport 06:01 - ORD 10:56 4h 55m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 06:01
        DFWDallas/Fort Worth Intl Airport 08:35
      • DFWDallas/Fort Worth Intl Airport 07:17
        ORDChicago O'Hare International Airport 10:56
      • 4h 55m (1h 18m)
      • 1 Stop DFW · Dallas 1h 18m
      • American Airlines (AA 2342)Boeing 737 800
        American Airlines (AA 328)Airbus
      • American Airlines (AA 2342)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:01 SAT
        10:58 ORD
        4Hrs, 57m 1 Stop (DFW)
      • SATSan Antonio International Airport 06:01 - ORD 10:58 4h 57m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 06:01
        DFWDallas/Fort Worth Intl Airport 08:35
      • DFWDallas/Fort Worth Intl Airport 07:17
        ORDChicago O'Hare International Airport 10:58
      • 4h 57m (1h 18m)
      • 1 Stop DFW · Dallas 1h 18m
      • American Airlines (AA 2342)Boeing 737 800
        American Airlines (AA 328)Airbus
      • American Airlines (AA 2342)
        • -
        • T
        • W
        • -
        • -
        • S
        • -
      • 06:10 SAT
        12:20 MDW
        6Hrs, 10m 1 Stop (ATL)
      • SATSan Antonio International Airport 06:10 - MDW 12:20 6h 10m 1 Stop (ATL) Atlanta
      • SATSan Antonio International Airport 06:10
        ATLAtlanta Hartsfield-Jackson Intl Airport 11:25
      • ATLAtlanta Hartsfield-Jackson Intl Airport 09:25
        MDWChicago Midway Airport 12:20
      • 6h 10m (2h)
      • 1 Stop ATL · Atlanta 2h
      • Southwest Airlines (WN 397)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 4846)Boeing 737 700
      • Southwest Airlines (WN 397)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:20 SAT
        11:30 ORD
        5Hrs, 10m 1 Stop (DAL)
      • SATSan Antonio International Airport 06:20 - ORD 11:30 5h 10m 1 Stop (DAL)
      • SATSan Antonio International Airport 06:20
        DALDallas/Fort Worth Love Field Airport 09:05
      • DALDallas/Fort Worth Love Field Airport 07:30
        ORDChicago O'Hare International Airport 11:30
      • 5h 10m (1h 35m)
      • 1 Stop DAL · 1h 35m
      • Southwest Airlines (WN 294)Boeing 737 800
        Southwest Airlines (WN 2318)Boeing 737 800
      • Southwest Airlines (WN 294)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:20 SAT
        12:00 MDW
        5Hrs, 40m 1 Stop (DAL)
      • SATSan Antonio International Airport 06:20 - MDW 12:00 5h 40m 1 Stop (DAL)
      • SATSan Antonio International Airport 06:20
        DALDallas/Fort Worth Love Field Airport 09:50
      • DALDallas/Fort Worth Love Field Airport 07:30
        MDWChicago Midway Airport 12:00
      • 5h 40m (2h 20m)
      • 1 Stop DAL · 2h 20m
      • Southwest Airlines (WN 294)Boeing 737 800
        Southwest Airlines (WN 1548)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 294)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:30 SAT
        12:45 MDW
        6Hrs, 15m 1 Stop (HOU)
      • SATSan Antonio International Airport 06:30 - MDW 12:45 6h 15m 1 Stop (HOU) Houston
      • SATSan Antonio International Airport 06:30
        HOUHouston Hobby Airport 10:20
      • HOUHouston Hobby Airport 07:25
        MDWChicago Midway Airport 12:45
      • 6h 15m (2h 55m)
      • 1 Stop HOU · Houston 2h 55m
      • Southwest Airlines (WN 527)Boeing 737 700
        Southwest Airlines (WN 2630)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 527)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:46 SAT
        12:15 ORD
        5Hrs, 29m 1 Stop (CLT)
      • SATSan Antonio International Airport 06:46 - ORD 12:15 5h 29m 1 Stop (CLT) Charlotte
      • SATSan Antonio International Airport 06:46
        CLTCharlotte Airport 11:10
      • CLTCharlotte Airport 10:30
        ORDChicago O'Hare International Airport 12:15
      • 5h 29m (40m)
      • 1 Stop CLT · Charlotte 40m
      • American Airlines (AA 388)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 388)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:46 SAT
        12:24 ORD
        5Hrs, 38m 1 Stop (CLT)
      • SATSan Antonio International Airport 06:46 - ORD 12:24 5h 38m 1 Stop (CLT) Charlotte
      • SATSan Antonio International Airport 06:46
        CLTCharlotte Airport 11:13
      • CLTCharlotte Airport 10:30
        ORDChicago O'Hare International Airport 12:24
      • 5h 38m (43m)
      • 1 Stop CLT · Charlotte 43m
      • American Airlines (AA 388)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 388)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:46 SAT
        13:10 ORD
        6Hrs, 24m 1 Stop (CLT)
      • SATSan Antonio International Airport 06:46 - ORD 13:10 6h 24m 1 Stop (CLT) Charlotte
      • SATSan Antonio International Airport 06:46
        CLTCharlotte Airport 11:40
      • CLTCharlotte Airport 10:30
        ORDChicago O'Hare International Airport 13:10
      • 6h 24m (1h 10m)
      • 1 Stop CLT · Charlotte 1h 10m
      • American Airlines (AA 388)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 388)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:57 SAT
        12:25 ORD
        5Hrs, 28m 1 Stop (DFW)
      • SATSan Antonio International Airport 06:57 - ORD 12:25 5h 28m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 06:57
        DFWDallas/Fort Worth Intl Airport 10:00
      • DFWDallas/Fort Worth Intl Airport 08:11
        ORDChicago O'Hare International Airport 12:25
      • 5h 28m (1h 49m)
      • 1 Stop DFW · Dallas 1h 49m
      • American Airlines (AA 3123)Airbus
        American Airlines (AA 2754)Boeing 737 800
      • American Airlines (AA 3123)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:57 SAT
        12:29 ORD
        5Hrs, 32m 1 Stop (DFW)
      • SATSan Antonio International Airport 06:57 - ORD 12:29 5h 32m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 06:57
        DFWDallas/Fort Worth Intl Airport 10:00
      • DFWDallas/Fort Worth Intl Airport 08:11
        ORDChicago O'Hare International Airport 12:29
      • 5h 32m (1h 49m)
      • 1 Stop DFW · Dallas 1h 49m
      • American Airlines (AA 3123)Airbus
        American Airlines (AA 2754)Boeing 737 800
      • American Airlines (AA 3123)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 06:57 SAT
        12:33 ORD
        5Hrs, 36m 1 Stop (DFW)
      • SATSan Antonio International Airport 06:57 - ORD 12:33 5h 36m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 06:57
        DFWDallas/Fort Worth Intl Airport 10:00
      • DFWDallas/Fort Worth Intl Airport 08:12
        ORDChicago O'Hare International Airport 12:33
      • 5h 36m (1h 48m)
      • 1 Stop DFW · Dallas 1h 48m
      • American Airlines (AA 3123)Airbus
        American Airlines (AA 2754)Airbus
      • American Airlines (AA 3123)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 06:57 SAT
        13:25 ORD
        6Hrs, 28m 1 Stop (DFW)
      • SATSan Antonio International Airport 06:57 - ORD 13:25 6h 28m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 06:57
        DFWDallas/Fort Worth Intl Airport 11:00
      • DFWDallas/Fort Worth Intl Airport 08:11
        ORDChicago O'Hare International Airport 13:25
      • 6h 28m (2h 49m)
      • 1 Stop DFW · Dallas 2h 49m
      • American Airlines (AA 3123)Airbus
        American Airlines (AA 311)Boeing 737 800
      • American Airlines (AA 3123)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:57 SAT
        13:26 ORD
        6Hrs, 29m 1 Stop (DFW)
      • SATSan Antonio International Airport 06:57 - ORD 13:26 6h 29m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 06:57
        DFWDallas/Fort Worth Intl Airport 11:00
      • DFWDallas/Fort Worth Intl Airport 08:12
        ORDChicago O'Hare International Airport 13:26
      • 6h 29m (2h 48m)
      • 1 Stop DFW · Dallas 2h 48m
      • American Airlines (AA 3123)Airbus
        American Airlines (AA 311)Boeing 737 800
      • American Airlines (AA 3123)
        • -
        • -
        • W
        • -
        • -
        • S
        • -
      • 06:57 SAT
        13:26 ORD
        6Hrs, 29m 1 Stop (DFW)
      • SATSan Antonio International Airport 06:57 - ORD 13:26 6h 29m 1 Stop (DFW) Dallas
      • SATSan Antonio International Airport 06:57
        DFWDallas/Fort Worth Intl Airport 11:00
      • DFWDallas/Fort Worth Intl Airport 08:11
        ORDChicago O'Hare International Airport 13:26
      • 6h 29m (2h 49m)
      • 1 Stop DFW · Dallas 2h 49m
      • American Airlines (AA 3123)Airbus
        American Airlines (AA 311)Boeing 737 800
      • American Airlines (AA 3123)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 07:00 SAT
        13:00 ORD
        6Hrs, 00m 1 Stop (BNA)
      • SATSan Antonio International Airport 07:00 - ORD 13:00 6h 1 Stop (BNA) Nashville
      • SATSan Antonio International Airport 07:00
        BNANashville Airport 11:15
      • BNANashville Airport 09:10
        ORDChicago O'Hare International Airport 13:00
      • 6h (2h 05m)
      • 1 Stop BNA · Nashville 2h 05m
      • Southwest Airlines (WN 653)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 5151)Boeing 737 800
      • Southwest Airlines (WN 653)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 07:10 SAT
        11:30 ORD
        4Hrs, 20m 1 Stop (DAL)
      • SATSan Antonio International Airport 07:10 - ORD 11:30 4h 20m 1 Stop (DAL)
      • SATSan Antonio International Airport 07:10
        DALDallas/Fort Worth Love Field Airport 09:05
      • DALDallas/Fort Worth Love Field Airport 08:20
        ORDChicago O'Hare International Airport 11:30
      • 4h 20m (45m)
      • 1 Stop DAL · 45m
      • Southwest Airlines (WN 3212)Boeing 737 800
        Southwest Airlines (WN 4429)Boeing 737 800
      • Southwest Airlines (WN 3212)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 07:18 SAT
        12:31 ORD
        5Hrs, 13m 1 Stop (IAH)
      • SATSan Antonio International Airport 07:18 - ORD 12:31 5h 13m 1 Stop (IAH) Houston
      • SATSan Antonio International Airport 07:18
        IAHHouston George Bush Intercontinental Airport 09:49
      • IAHHouston George Bush Intercontinental Airport 08:22
        ORDChicago O'Hare International Airport 12:31
      • 5h 13m (1h 27m)
      • 1 Stop IAH · Houston 1h 27m
      • United Airlines (UA 1486)Boeing 737 800
        United Airlines (UA 1321)Boeing 737 900
      • United Airlines (UA 1486)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 07:20 SAT
        12:00 MDW
        4Hrs, 40m 1 Stop (BNA)
      • SATSan Antonio International Airport 07:20 - MDW 12:00 4h 40m 1 Stop (BNA) Nashville
      • SATSan Antonio International Airport 07:20
        BNANashville Airport 10:20
      • BNANashville Airport 09:25
        MDWChicago Midway Airport 12:00
      • 4h 40m (55m)
      • 1 Stop BNA · Nashville 55m
      • Southwest Airlines (WN 653)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 4877)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 653)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:43 SAT
        14:19 ORD
        6Hrs, 36m 1 Stop (IAD)
      • SATSan Antonio International Airport 07:43 - ORD 14:19 6h 36m 1 Stop (IAD) Washington
      • SATSan Antonio International Airport 07:43
        IADWashington Dulles International Airport 13:05
      • IADWashington Dulles International Airport 11:55
        ORDChicago O'Hare International Airport 14:19
      • 6h 36m (1h 10m)
      • 1 Stop IAD · Washington 1h 10m
      • United Airlines (UA 1347)Boeing 737 900
        United Airlines (UA 673)Boeing 737 700
      • United Airlines (UA 1347)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 07:43 SAT
        14:19 ORD
        6Hrs, 36m 1 Stop (IAD)
      • SATSan Antonio International Airport 07:43 - ORD 14:19 6h 36m 1 Stop (IAD) Washington
      • SATSan Antonio International Airport 07:43
        IADWashington Dulles International Airport 13:05
      • IADWashington Dulles International Airport 11:55
        ORDChicago O'Hare International Airport 14:19
      • 6h 36m (1h 10m)
      • 1 Stop IAD · Washington 1h 10m
      • United Airlines (UA 1347)Boeing 737 900
        United Airlines (UA 673)Boeing 737 800
      • United Airlines (UA 1347)
        • M
        • T
        • W
        • T
        • F
        • S
        • -
      No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
      What’s the fastest flight time from San Antonio to Chicago?

      The fastest flight time for direct flights from San Antonio to Chicago is 2 hours 30 minutes. Check latest flight schedules & prices on Wego.

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

      The most popular airline flying from San Antonio to Chicago is United Airlines. Find the latest flight deals on Wego.

      How far is Chicago from San Antonio?

      The flight distance between San Antonio and Chicago is 1694km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 05:00. The last flight of the day departs at 18:20. See the full list of flight times on Wego.

      How many airlines offer direct flights from San Antonio to Chicago?

      There are 3 airlines that offer direct flights from San Antonio to Chicago. Find out the list of airlines on Wego.

      All Airports in San Antonio

      San Antonio International Airport SAT

      Martindale AHP MDA

      Popular Airlines flying from San Antonio to Chicago

      United Airlines ‏()
      American Airlines ‏()

      Popular Destinations from Chicago

      Popular Destinations from San Antonio

      Popular Hotels in Chicago

      Hotels In Popular Destinations