Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Frontier Airlines

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

  • Frontier Airlines Frontier Airlines
  • Spirit Airlines Spirit Airlines
  • United Airlines United Airlines
  • Contour Airlines Contour Airlines
  • American Airlines American Airlines
  • Southwest Airlines Southwest Airlines
  • Alaska Airlines Alaska Airlines
  • JetBlue Airways JetBlue Airways
Cheapest Month February

Travel Period: February 2025 - January 2026

The cheapest month(s) to fly from Dallas to Chicago is February.

  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
  • Jan 2026
Cheapest Day of the Week Saturday

The cheapest day(s) of the week to fly from Dallas to Chicago is Saturday.

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

Flight Schedules

Last Updated: Thu, 2 Jan, 2025

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  • Availability
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 18:40 DAL
    20:50 MDW
    2Hrs, 10m Direct
  • DALDallas/Fort Worth Love Field Airport 18:40 - MDW 20:50 2h 10m Direct
  • DALDallas/Fort Worth Love Field Airport 18:40
  • MDWChicago Midway Airport 20:50
  • 2h 10m
  • Direct
  • Southwest Airlines (WN 1413)Boeing 737 700
  • Southwest Airlines (WN 1413)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 700
  • 19:10 DAL
    21:30 ORD
    2Hrs, 20m Direct
  • DALDallas/Fort Worth Love Field Airport 19:10 - ORD 21:30 2h 20m Direct
  • DALDallas/Fort Worth Love Field Airport 19:10
  • ORDChicago O'Hare International Airport 21:30
  • 2h 20m
  • Direct
  • Southwest Airlines (WN 2322)Boeing 737 700
  • Southwest Airlines (WN 2322)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 20:00 DAL
    22:10 MDW
    2Hrs, 10m Direct
  • DALDallas/Fort Worth Love Field Airport 20:00 - MDW 22:10 2h 10m Direct
  • DALDallas/Fort Worth Love Field Airport 20:00
  • MDWChicago Midway Airport 22:10
  • 2h 10m
  • Direct
  • Southwest Airlines (WN 2866)Boeing 737 700
  • Southwest Airlines (WN 2866)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 20:17 DFW
    22:46 ORD
    2Hrs, 29m Direct
  • DFWDallas/Fort Worth Intl Airport 20:17 - ORD 22:46 2h 29m Direct
  • DFWDallas/Fort Worth Intl Airport 20:17
  • ORDChicago O'Hare International Airport 22:46
  • 2h 29m
  • Direct
  • Frontier Airlines (F9 1342)Airbus A321 Neo
  • Frontier Airlines (F9 1342)
    • -
    • -
    • -
    • -
    • F
    • -
    • -
  • Airbus A321 Neo
  • 20:25 DAL
    22:35 MDW
    2Hrs, 10m Direct
  • DALDallas/Fort Worth Love Field Airport 20:25 - MDW 22:35 2h 10m Direct
  • DALDallas/Fort Worth Love Field Airport 20:25
  • MDWChicago Midway Airport 22:35
  • 2h 10m
  • Direct
  • Southwest Airlines (WN 1317)Boeing 737 700
  • Southwest Airlines (WN 1317)
    • -
    • -
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 700
  • 20:28 DFW
    22:57 ORD
    2Hrs, 29m Direct
  • DFWDallas/Fort Worth Intl Airport 20:28 - ORD 22:57 2h 29m Direct
  • DFWDallas/Fort Worth Intl Airport 20:28
  • ORDChicago O'Hare International Airport 22:57
  • 2h 29m
  • Direct
  • Frontier Airlines (F9 1342)Airbus A321 Neo
  • Frontier Airlines (F9 1342)
    • M
    • -
    • -
    • -
    • -
    • -
    • -
  • Airbus A321 Neo
  • 21:03 DFW
    23:20 MDW
    2Hrs, 17m Direct
  • DFWDallas/Fort Worth Intl Airport 21:03 - MDW 23:20 2h 17m Direct
  • DFWDallas/Fort Worth Intl Airport 21:03
  • MDWChicago Midway Airport 23:20
  • 2h 17m
  • Direct
  • Frontier Airlines (F9 2998)Airbus A320 Neo
  • Frontier Airlines (F9 2998)
    • M
    • T
    • W
    • -
    • -
    • S
    • -
  • Airbus A320 Neo
  • 21:14 DFW
    23:31 MDW
    2Hrs, 17m Direct
  • DFWDallas/Fort Worth Intl Airport 21:14 - MDW 23:31 2h 17m Direct
  • DFWDallas/Fort Worth Intl Airport 21:14
  • MDWChicago Midway Airport 23:31
  • 2h 17m
  • Direct
  • Frontier Airlines (F9 2998)Airbus A320 Neo
  • Frontier Airlines (F9 2998)
    • -
    • -
    • -
    • T
    • -
    • -
    • -
  • Airbus A320 Neo
  • 21:18 DFW
    23:35 MDW
    2Hrs, 17m Direct
  • DFWDallas/Fort Worth Intl Airport 21:18 - MDW 23:35 2h 17m Direct
  • DFWDallas/Fort Worth Intl Airport 21:18
  • MDWChicago Midway Airport 23:35
  • 2h 17m
  • Direct
  • Frontier Airlines (F9 2998)Airbus A320 Neo
  • Frontier Airlines (F9 2998)
    • -
    • -
    • -
    • -
    • F
    • -
    • -
  • Airbus A320 Neo
  • 21:23 DFW
    23:40 MDW
    2Hrs, 17m Direct
  • DFWDallas/Fort Worth Intl Airport 21:23 - MDW 23:40 2h 17m Direct
  • DFWDallas/Fort Worth Intl Airport 21:23
  • MDWChicago Midway Airport 23:40
  • 2h 17m
  • Direct
  • Frontier Airlines (F9 2998)Airbus A320 Neo
  • Frontier Airlines (F9 2998)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Airbus A320 Neo
  • 05:00 DFW
    07:20 ORD
    2Hrs, 20m Direct
  • DFWDallas/Fort Worth Intl Airport 05:00 - ORD 07:20 2h 20m Direct
  • DFWDallas/Fort Worth Intl Airport 05:00
  • ORDChicago O'Hare International Airport 07:20
  • 2h 20m
  • Direct
  • American Airlines (AA 2812)Boeing 737 800
  • American Airlines (AA 2812)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 06:00 DFW
    08:25 ORD
    2Hrs, 25m Direct
  • DFWDallas/Fort Worth Intl Airport 06:00 - ORD 08:25 2h 25m Direct
  • DFWDallas/Fort Worth Intl Airport 06:00
  • ORDChicago O'Hare International Airport 08:25
  • 2h 25m
  • Direct
  • American Airlines (AA 3012)Boeing 737 800
  • American Airlines (AA 3012)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 800
  • 06:00 DFW
    08:25 ORD
    2Hrs, 25m Direct
  • DFWDallas/Fort Worth Intl Airport 06:00 - ORD 08:25 2h 25m Direct
  • DFWDallas/Fort Worth Intl Airport 06:00
  • ORDChicago O'Hare International Airport 08:25
  • 2h 25m
  • Direct
  • American Airlines (AA 3076)Boeing 737 800
  • American Airlines (AA 3076)
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • Boeing 737 800
  • 06:30 DAL
    08:40 MDW
    2Hrs, 10m Direct
  • DALDallas/Fort Worth Love Field Airport 06:30 - MDW 08:40 2h 10m Direct
  • DALDallas/Fort Worth Love Field Airport 06:30
  • MDWChicago Midway Airport 08:40
  • 2h 10m
  • Direct
  • Southwest Airlines (WN 2387)Boeing 737 800
  • Southwest Airlines (WN 2387)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 800
  • 07:00 DFW
    09:25 ORD
    2Hrs, 25m Direct
  • DFWDallas/Fort Worth Intl Airport 07:00 - ORD 09:25 2h 25m Direct
  • DFWDallas/Fort Worth Intl Airport 07:00
  • ORDChicago O'Hare International Airport 09:25
  • 2h 25m
  • Direct
  • American Airlines (AA 1106)Boeing 737 800
  • American Airlines (AA 1106)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 07:00 DFW
    09:30 ORD
    2Hrs, 30m Direct
  • DFWDallas/Fort Worth Intl Airport 07:00 - ORD 09:30 2h 30m Direct
  • DFWDallas/Fort Worth Intl Airport 07:00
  • ORDChicago O'Hare International Airport 09:30
  • 2h 30m
  • Direct
  • United Airlines (UA 380)Airbus
  • United Airlines (UA 380)
    • M
    • T
    • -
    • T
    • F
    • -
    • -
  • Airbus
  • 07:05 DAL
    09:15 MDW
    2Hrs, 10m Direct
  • DALDallas/Fort Worth Love Field Airport 07:05 - MDW 09:15 2h 10m Direct
  • DALDallas/Fort Worth Love Field Airport 07:05
  • MDWChicago Midway Airport 09:15
  • 2h 10m
  • Direct
  • Southwest Airlines (WN 1969)Boeing 737 700
  • Southwest Airlines (WN 1969)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 700
  • 08:30 DAL
    12:15 MDW
    3Hrs, 45m Direct
  • DALDallas/Fort Worth Love Field Airport 08:30 - MDW 12:15 3h 45m Direct
  • DALDallas/Fort Worth Love Field Airport 08:30
  • MDWChicago Midway Airport 12:15
  • 3h 45m
  • Direct
  • Southwest Airlines (WN 1381)Boeing 737 700
  • Southwest Airlines (WN 1381)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 08:35 DAL
    10:45 MDW
    2Hrs, 10m Direct
  • DALDallas/Fort Worth Love Field Airport 08:35 - MDW 10:45 2h 10m Direct
  • DALDallas/Fort Worth Love Field Airport 08:35
  • MDWChicago Midway Airport 10:45
  • 2h 10m
  • Direct
  • Southwest Airlines (WN 2330)Boeing 737 700
  • Southwest Airlines (WN 2330)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 09:05 DAL
    11:30 ORD
    2Hrs, 25m Direct
  • DALDallas/Fort Worth Love Field Airport 09:05 - ORD 11:30 2h 25m Direct
  • DALDallas/Fort Worth Love Field Airport 09:05
  • ORDChicago O'Hare International Airport 11:30
  • 2h 25m
  • Direct
  • Southwest Airlines (WN 2318)Boeing 737 800
  • Southwest Airlines (WN 2318)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 800
  • 09:05 DAL
    11:30 ORD
    2Hrs, 25m Direct
  • DALDallas/Fort Worth Love Field Airport 09:05 - ORD 11:30 2h 25m Direct
  • DALDallas/Fort Worth Love Field Airport 09:05
  • ORDChicago O'Hare International Airport 11:30
  • 2h 25m
  • Direct
  • Southwest Airlines (WN 309)Boeing 737 800
  • Southwest Airlines (WN 309)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 800
  • 09:50 DAL
    12:00 MDW
    2Hrs, 10m Direct
  • DALDallas/Fort Worth Love Field Airport 09:50 - MDW 12:00 2h 10m Direct
  • DALDallas/Fort Worth Love Field Airport 09:50
  • MDWChicago Midway Airport 12:00
  • 2h 10m
  • Direct
  • Southwest Airlines (WN 1548)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 1548)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 10:20 DFW
    12:59 ORD
    2Hrs, 39m Direct
  • DFWDallas/Fort Worth Intl Airport 10:20 - ORD 12:59 2h 39m Direct
  • DFWDallas/Fort Worth Intl Airport 10:20
  • ORDChicago O'Hare International Airport 12:59
  • 2h 39m
  • Direct
  • American Airlines (AA 2754)Boeing 737 800
  • American Airlines (AA 2754)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 11:57 DFW
    14:26 ORD
    2Hrs, 29m Direct
  • DFWDallas/Fort Worth Intl Airport 11:57 - ORD 14:26 2h 29m Direct
  • DFWDallas/Fort Worth Intl Airport 11:57
  • ORDChicago O'Hare International Airport 14:26
  • 2h 29m
  • Direct
  • Frontier Airlines (F9 3244)Airbus A320 Neo
  • Frontier Airlines (F9 3244)
    • -
    • T
    • -
    • -
    • -
    • -
    • -
  • Airbus A320 Neo
  • 12:20 DAL
    14:30 MDW
    2Hrs, 10m Direct
  • DALDallas/Fort Worth Love Field Airport 12:20 - MDW 14:30 2h 10m Direct
  • DALDallas/Fort Worth Love Field Airport 12:20
  • MDWChicago Midway Airport 14:30
  • 2h 10m
  • Direct
  • Southwest Airlines (WN 3836)Boeing 737 800
  • Southwest Airlines (WN 3836)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 800
  • 12:40 DAL
    15:00 ORD
    2Hrs, 20m Direct
  • DALDallas/Fort Worth Love Field Airport 12:40 - ORD 15:00 2h 20m Direct
  • DALDallas/Fort Worth Love Field Airport 12:40
  • ORDChicago O'Hare International Airport 15:00
  • 2h 20m
  • Direct
  • Southwest Airlines (WN 4903)Boeing 737 800
  • Southwest Airlines (WN 4903)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 800
  • 12:50 DAL
    16:20 MDW
    3Hrs, 30m Direct
  • DALDallas/Fort Worth Love Field Airport 12:50 - MDW 16:20 3h 30m Direct
  • DALDallas/Fort Worth Love Field Airport 12:50
  • MDWChicago Midway Airport 16:20
  • 3h 30m
  • Direct
  • Southwest Airlines (WN 2951)Boeing 737 700
  • Southwest Airlines (WN 2951)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 13:10 DAL
    16:45 MDW
    3Hrs, 35m Direct
  • DALDallas/Fort Worth Love Field Airport 13:10 - MDW 16:45 3h 35m Direct
  • DALDallas/Fort Worth Love Field Airport 13:10
  • MDWChicago Midway Airport 16:45
  • 3h 35m
  • Direct
  • Southwest Airlines (WN 980)Boeing 737 700
  • Southwest Airlines (WN 980)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 700
  • 13:35 DAL
    15:45 MDW
    2Hrs, 10m Direct
  • DALDallas/Fort Worth Love Field Airport 13:35 - MDW 15:45 2h 10m Direct
  • DALDallas/Fort Worth Love Field Airport 13:35
  • MDWChicago Midway Airport 15:45
  • 2h 10m
  • Direct
  • Southwest Airlines (WN 2564)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 2564)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 14:05 DAL
    16:15 MDW
    2Hrs, 10m Direct
  • DALDallas/Fort Worth Love Field Airport 14:05 - MDW 16:15 2h 10m Direct
  • DALDallas/Fort Worth Love Field Airport 14:05
  • MDWChicago Midway Airport 16:15
  • 2h 10m
  • Direct
  • Southwest Airlines (WN 2564)Boeing 737 800
  • Southwest Airlines (WN 2564)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 800
  • 14:45 DFW
    17:10 ORD
    2Hrs, 25m Direct
  • DFWDallas/Fort Worth Intl Airport 14:45 - ORD 17:10 2h 25m Direct
  • DFWDallas/Fort Worth Intl Airport 14:45
  • ORDChicago O'Hare International Airport 17:10
  • 2h 25m
  • Direct
  • United Airlines (UA 1324)Boeing 737 800
  • United Airlines (UA 1324)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 15:14 DFW
    17:36 ORD
    2Hrs, 22m Direct
  • DFWDallas/Fort Worth Intl Airport 15:14 - ORD 17:36 2h 22m Direct
  • DFWDallas/Fort Worth Intl Airport 15:14
  • ORDChicago O'Hare International Airport 17:36
  • 2h 22m
  • Direct
  • American Airlines (AA 2412)Boeing 737 800
  • American Airlines (AA 2412)
    • -
    • -
    • -
    • T
    • -
    • -
    • -
  • Boeing 737 800
  • 15:45 DAL
    18:10 ORD
    2Hrs, 25m Direct
  • DALDallas/Fort Worth Love Field Airport 15:45 - ORD 18:10 2h 25m Direct
  • DALDallas/Fort Worth Love Field Airport 15:45
  • ORDChicago O'Hare International Airport 18:10
  • 2h 25m
  • Direct
  • Southwest Airlines (WN 4042)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 4042)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 16:50 DAL
    19:00 MDW
    2Hrs, 10m Direct
  • DALDallas/Fort Worth Love Field Airport 16:50 - MDW 19:00 2h 10m Direct
  • DALDallas/Fort Worth Love Field Airport 16:50
  • MDWChicago Midway Airport 19:00
  • 2h 10m
  • Direct
  • Southwest Airlines (WN 3687)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 3687)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 17:30 DAL
    19:40 MDW
    2Hrs, 10m Direct
  • DALDallas/Fort Worth Love Field Airport 17:30 - MDW 19:40 2h 10m Direct
  • DALDallas/Fort Worth Love Field Airport 17:30
  • MDWChicago Midway Airport 19:40
  • 2h 10m
  • Direct
  • Southwest Airlines (WN 2045)Boeing 737 800
  • Southwest Airlines (WN 2045)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 800
  • 17:45 DFW
    20:14 ORD
    2Hrs, 29m Direct
  • DFWDallas/Fort Worth Intl Airport 17:45 - ORD 20:14 2h 29m Direct
  • DFWDallas/Fort Worth Intl Airport 17:45
  • ORDChicago O'Hare International Airport 20:14
  • 2h 29m
  • Direct
  • United Airlines (UA 1436)Airbus
  • United Airlines (UA 1436)
    • -
    • -
    • -
    • -
    • F
    • S
    • -
  • Airbus
  • 18:15 DAL
    23:55 MDW
    5Hrs, 40m 1 Stop (STL)
  • DALDallas/Fort Worth Love Field Airport 18:15 - MDW 23:55 5h 40m 1 Stop (STL) Saint Louis
  • DALDallas/Fort Worth Love Field Airport 18:15
    STLSt Louis Lambert Intl Airport 22:45
  • STLSt Louis Lambert Intl Airport 19:55
    MDWChicago Midway Airport 23:55
  • 5h 40m (2h 50m)
  • 1 Stop STL · Saint Louis 2h 50m
  • Southwest Airlines (WN 3917)Boeing 737 800
    Southwest Airlines (WN 652)Boeing 737 700
  • Southwest Airlines (WN 3917)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 18:45 DAL
    00:35 MDW
    5Hrs, 50m 1 Stop (DEN)
  • DALDallas/Fort Worth Love Field Airport 18:45 - MDW 00:35 5h 50m 1 Stop (DEN) Denver
  • DALDallas/Fort Worth Love Field Airport 18:45
    DENDenver Intl Airport 21:20
  • DENDenver Intl Airport 19:45
    MDWChicago Midway Airport 00:35
  • 5h 50m (1h 35m)
  • 1 Stop DEN · Denver 1h 35m
  • Southwest Airlines (WN 3805)Boeing 737 800
    Southwest Airlines (WN 4514)Boeing 737 800
  • Southwest Airlines (WN 3805)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 19:00 DFW
    23:57 ORD
    4Hrs, 57m 1 Stop (IAH)
  • DFWDallas/Fort Worth Intl Airport 19:00 - ORD 23:57 4h 57m 1 Stop (IAH) Houston
  • DFWDallas/Fort Worth Intl Airport 19:00
    IAHHouston George Bush Intercontinental Airport 21:20
  • IAHHouston George Bush Intercontinental Airport 20:20
    ORDChicago O'Hare International Airport 23:57
  • 4h 57m (1h)
  • 1 Stop IAH · Houston 1h
  • Frontier Airlines (F9 3198)Airbus A320 Neo
    Frontier Airlines (F9 3136)Airbus A320 Neo
  • Frontier Airlines (F9 3198)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 19:12 DFW
    23:59 ORD
    4Hrs, 47m 1 Stop (IAH)
  • DFWDallas/Fort Worth Intl Airport 19:12 - ORD 23:59 4h 47m 1 Stop (IAH) Houston
  • DFWDallas/Fort Worth Intl Airport 19:12
    IAHHouston George Bush Intercontinental Airport 21:22
  • IAHHouston George Bush Intercontinental Airport 20:32
    ORDChicago O'Hare International Airport 23:59
  • 4h 47m (50m)
  • 1 Stop IAH · Houston 50m
  • Frontier Airlines (F9 3198)Airbus A320 Neo
    Frontier Airlines (F9 3136)Airbus A320 Neo
  • Frontier Airlines (F9 3198)
    • -
    • T
    • -
    • -
    • -
    • -
    • -
  • 05:45 DFW
    11:25 ORD
    5Hrs, 40m 1 Stop (DEN)
  • DFWDallas/Fort Worth Intl Airport 05:45 - ORD 11:25 5h 40m 1 Stop (DEN) Denver
  • DFWDallas/Fort Worth Intl Airport 05:45
    DENDenver Intl Airport 07:50
  • DENDenver Intl Airport 06:55
    ORDChicago O'Hare International Airport 11:25
  • 5h 40m (55m)
  • 1 Stop DEN · Denver 55m
  • United Airlines (UA 1005)Boeing 737 Max 9 Passenger
    United Airlines (UA 1811)Boeing 777
  • United Airlines (UA 1005)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 05:45 DFW
    11:25 ORD
    5Hrs, 40m 1 Stop (DEN)
  • DFWDallas/Fort Worth Intl Airport 05:45 - ORD 11:25 5h 40m 1 Stop (DEN) Denver
  • DFWDallas/Fort Worth Intl Airport 05:45
    DENDenver Intl Airport 07:50
  • DENDenver Intl Airport 06:55
    ORDChicago O'Hare International Airport 11:25
  • 5h 40m (55m)
  • 1 Stop DEN · Denver 55m
  • United Airlines (UA 1005)Airbus
    United Airlines (UA 1811)Boeing 777
  • United Airlines (UA 1005)
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • 06:00 DAL
    09:25 MDW
    3Hrs, 25m 1 Stop (STL)
  • DALDallas/Fort Worth Love Field Airport 06:00 - MDW 09:25 3h 25m 1 Stop (STL) Saint Louis
  • DALDallas/Fort Worth Love Field Airport 06:00
    STLSt Louis Lambert Intl Airport 08:15
  • STLSt Louis Lambert Intl Airport 07:40
    MDWChicago Midway Airport 09:25
  • 3h 25m (35m)
  • 1 Stop STL · Saint Louis 35m
  • Southwest Airlines (WN 1859)Boeing 737 700
    Southwest Airlines (WN 498)Boeing 737 700
  • Southwest Airlines (WN 1859)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 06:05 DAL
    11:50 MDW
    5Hrs, 45m 1 Stop (STL)
  • DALDallas/Fort Worth Love Field Airport 06:05 - MDW 11:50 5h 45m 1 Stop (STL) Saint Louis
  • DALDallas/Fort Worth Love Field Airport 06:05
    STLSt Louis Lambert Intl Airport 10:40
  • STLSt Louis Lambert Intl Airport 07:45
    MDWChicago Midway Airport 11:50
  • 5h 45m (2h 55m)
  • 1 Stop STL · Saint Louis 2h 55m
  • Southwest Airlines (WN 1859)Boeing 737 800
    Southwest Airlines (WN 2364)Boeing 737 800
  • Southwest Airlines (WN 1859)
    • -
    • T
    • -
    • -
    • -
    • -
    • -
  • 06:10 DAL
    10:40 MDW
    4Hrs, 30m 1 Stop (SAT)
  • DALDallas/Fort Worth Love Field Airport 06:10 - MDW 10:40 4h 30m 1 Stop (SAT) San Antonio
  • DALDallas/Fort Worth Love Field Airport 06:10
    SATSan Antonio International Airport 08:10
  • SATSan Antonio International Airport 07:20
    MDWChicago Midway Airport 10:40
  • 4h 30m (50m)
  • 1 Stop SAT · San Antonio 50m
  • Southwest Airlines (WN 1657)Boeing 737 700
    Southwest Airlines (WN 2243)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 1657)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 06:15 DAL
    11:15 MDW
    5Hrs, 00m 1 Stop (HOU)
  • DALDallas/Fort Worth Love Field Airport 06:15 - MDW 11:15 5h 1 Stop (HOU) Houston
  • DALDallas/Fort Worth Love Field Airport 06:15
    HOUHouston Hobby Airport 08:50
  • HOUHouston Hobby Airport 07:25
    MDWChicago Midway Airport 11:15
  • 5h (1h 25m)
  • 1 Stop HOU · Houston 1h 25m
  • Southwest Airlines (WN 5)Boeing 737 700
    Southwest Airlines (WN 222)Boeing 737 800
  • Southwest Airlines (WN 5)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 06:15 DAL
    12:15 MDW
    6Hrs, 00m 1 Stop (MCO)
  • DALDallas/Fort Worth Love Field Airport 06:15 - MDW 12:15 6h 1 Stop (MCO) Orlando
  • DALDallas/Fort Worth Love Field Airport 06:15
    MCOOrlando International Airport 10:25
  • MCOOrlando International Airport 09:45
    MDWChicago Midway Airport 12:15
  • 6h (40m)
  • 1 Stop MCO · Orlando 40m
  • Southwest Airlines (WN 2624)Boeing 737 Max 8 Passenger
    Southwest Airlines (WN 546)Boeing 737 800
  • Southwest Airlines (WN 2624)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 06:45 DAL
    11:55 MDW
    5Hrs, 10m 1 Stop (MCI)
  • DALDallas/Fort Worth Love Field Airport 06:45 - MDW 11:55 5h 10m 1 Stop (MCI) Kansas City
  • DALDallas/Fort Worth Love Field Airport 06:45
    MCIKansas City International Airport 10:30
  • MCIKansas City International Airport 08:15
    MDWChicago Midway Airport 11:55
  • 5h 10m (2h 15m)
  • 1 Stop MCI · Kansas City 2h 15m
  • Southwest Airlines (WN 3080)Boeing 737 700
    Southwest Airlines (WN 2847)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 3080)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 07:00 DFW
    11:08 ORD
    4Hrs, 08m 1 Stop (IND)
  • DFWDallas/Fort Worth Intl Airport 07:00 - ORD 11:08 4h 08m 1 Stop (IND) Indianapolis
  • DFWDallas/Fort Worth Intl Airport 07:00
    INDIndianapolis Airport 10:55
  • INDIndianapolis Airport 10:11
    ORDChicago O'Hare International Airport 11:08
  • 4h 08m (44m)
  • 1 Stop IND · Indianapolis 44m
  • American Airlines (AA 2456)Boeing 737 800
    American Airlines (AA 3713)Embraer 170
  • American Airlines (AA 2456)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 07:00 DAL
    13:00 MDW
    6Hrs, 00m 1 Stop (MCO)
  • DALDallas/Fort Worth Love Field Airport 07:00 - MDW 13:00 6h 1 Stop (MCO) Orlando
  • DALDallas/Fort Worth Love Field Airport 07:00
    MCOOrlando International Airport 11:05
  • MCOOrlando International Airport 10:30
    MDWChicago Midway Airport 13:00
  • 6h (35m)
  • 1 Stop MCO · Orlando 35m
  • Southwest Airlines (WN 1536)Boeing 737 700
    Southwest Airlines (WN 3764)Boeing 737 800
  • Southwest Airlines (WN 1536)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 07:05 DFW
    11:08 ORD
    4Hrs, 03m 1 Stop (IND)
  • DFWDallas/Fort Worth Intl Airport 07:05 - ORD 11:08 4h 03m 1 Stop (IND) Indianapolis
  • DFWDallas/Fort Worth Intl Airport 07:05
    INDIndianapolis Airport 10:55
  • INDIndianapolis Airport 10:16
    ORDChicago O'Hare International Airport 11:08
  • 4h 03m (39m)
  • 1 Stop IND · Indianapolis 39m
  • American Airlines (AA 2456)Boeing 737 800
    American Airlines (AA 3713)Embraer 170
  • American Airlines (AA 2456)
    • M
    • T
    • -
    • T
    • F
    • -
    • -
  • 07:10 DAL
    13:00 MDW
    5Hrs, 50m 1 Stop (DEN)
  • DALDallas/Fort Worth Love Field Airport 07:10 - MDW 13:00 5h 50m 1 Stop (DEN) Denver
  • DALDallas/Fort Worth Love Field Airport 07:10
    DENDenver Intl Airport 09:40
  • DENDenver Intl Airport 08:15
    MDWChicago Midway Airport 13:00
  • 5h 50m (1h 25m)
  • 1 Stop DEN · Denver 1h 25m
  • Southwest Airlines (WN 3226)Boeing 737 Max 8 Passenger
    Southwest Airlines (WN 1329)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 3226)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 07:10 DFW
    11:53 ORD
    4Hrs, 43m 1 Stop (DTW)
  • DFWDallas/Fort Worth Intl Airport 07:10 - ORD 11:53 4h 43m 1 Stop (DTW) Detroit
  • DFWDallas/Fort Worth Intl Airport 07:10
    DTWDetroit Wayne County 11:28
  • DTWDetroit Wayne County 10:51
    ORDChicago O'Hare International Airport 11:53
  • 4h 43m (37m)
  • 1 Stop DTW · Detroit 37m
  • American Airlines (AA 1715)Airbus
    American Airlines (AA 3653)Embraer 170
  • American Airlines (AA 1715)
    • -
    • -
    • -
    • T
    • -
    • -
    • -
  • 07:15 DAL
    13:00 ORD
    5Hrs, 45m 1 Stop (BNA)
  • DALDallas/Fort Worth Love Field Airport 07:15 - ORD 13:00 5h 45m 1 Stop (BNA) Nashville
  • DALDallas/Fort Worth Love Field Airport 07:15
    BNANashville Airport 11:15
  • BNANashville Airport 09:00
    ORDChicago O'Hare International Airport 13:00
  • 5h 45m (2h 15m)
  • 1 Stop BNA · Nashville 2h 15m
  • Southwest Airlines (WN 1077)Boeing 737 Max 8 Passenger
    Southwest Airlines (WN 467)Boeing 737 800
  • Southwest Airlines (WN 1077)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 07:50 DAL
    13:30 MDW
    5Hrs, 40m 1 Stop (BWI)
  • DALDallas/Fort Worth Love Field Airport 07:50 - MDW 13:30 5h 40m 1 Stop (BWI) Baltimore
  • DALDallas/Fort Worth Love Field Airport 07:50
    BWIBaltimore Washington International Airport 12:25
  • BWIBaltimore Washington International Airport 11:40
    MDWChicago Midway Airport 13:30
  • 5h 40m (45m)
  • 1 Stop BWI · Baltimore 45m
  • Southwest Airlines (WN 3463)Boeing 737 800
    Southwest Airlines (WN 2833)Boeing 737 800
  • Southwest Airlines (WN 3463)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 08:10 DAL
    11:50 MDW
    3Hrs, 40m 1 Stop (STL)
  • DALDallas/Fort Worth Love Field Airport 08:10 - MDW 11:50 3h 40m 1 Stop (STL) Saint Louis
  • DALDallas/Fort Worth Love Field Airport 08:10
    STLSt Louis Lambert Intl Airport 10:40
  • STLSt Louis Lambert Intl Airport 09:50
    MDWChicago Midway Airport 11:50
  • 3h 40m (50m)
  • 1 Stop STL · Saint Louis 50m
  • Southwest Airlines (WN 3050)Boeing 737 700
    Southwest Airlines (WN 2364)Boeing 737 800
  • Southwest Airlines (WN 3050)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 08:15 DAL
    13:00 ORD
    4Hrs, 45m 1 Stop (BNA)
  • DALDallas/Fort Worth Love Field Airport 08:15 - ORD 13:00 4h 45m 1 Stop (BNA) Nashville
  • DALDallas/Fort Worth Love Field Airport 08:15
    BNANashville Airport 11:15
  • BNANashville Airport 10:00
    ORDChicago O'Hare International Airport 13:00
  • 4h 45m (1h 15m)
  • 1 Stop BNA · Nashville 1h 15m
  • Southwest Airlines (WN 1623)Boeing 737 Max 8 Passenger
    Southwest Airlines (WN 983)Boeing 737 800
  • Southwest Airlines (WN 1623)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 09:00 DAL
    14:15 MDW
    5Hrs, 15m 1 Stop (HOU)
  • DALDallas/Fort Worth Love Field Airport 09:00 - MDW 14:15 5h 15m 1 Stop (HOU) Houston
  • DALDallas/Fort Worth Love Field Airport 09:00
    HOUHouston Hobby Airport 11:50
  • HOUHouston Hobby Airport 10:10
    MDWChicago Midway Airport 14:15
  • 5h 15m (1h 40m)
  • 1 Stop HOU · Houston 1h 40m
  • Southwest Airlines (WN 9)Boeing 737 700
    Southwest Airlines (WN 2630)Boeing 737 800
  • Southwest Airlines (WN 9)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 09:00 DAL
    14:00 MDW
    5Hrs, 00m 1 Stop (BNA)
  • DALDallas/Fort Worth Love Field Airport 09:00 - MDW 14:00 5h 1 Stop (BNA) Nashville
  • DALDallas/Fort Worth Love Field Airport 09:00
    BNANashville Airport 12:25
  • BNANashville Airport 10:45
    MDWChicago Midway Airport 14:00
  • 5h (1h 40m)
  • 1 Stop BNA · Nashville 1h 40m
  • Southwest Airlines (WN 2743)Boeing 737 800
    Southwest Airlines (WN 2412)Boeing 737 700
  • Southwest Airlines (WN 2743)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 09:10 DAL
    14:25 MDW
    5Hrs, 15m 1 Stop (STL)
  • DALDallas/Fort Worth Love Field Airport 09:10 - MDW 14:25 5h 15m 1 Stop (STL) Saint Louis
  • DALDallas/Fort Worth Love Field Airport 09:10
    STLSt Louis Lambert Intl Airport 13:20
  • STLSt Louis Lambert Intl Airport 10:50
    MDWChicago Midway Airport 14:25
  • 5h 15m (2h 30m)
  • 1 Stop STL · Saint Louis 2h 30m
  • Southwest Airlines (WN 2002)Boeing 737 700
    Southwest Airlines (WN 2906)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 2002)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 09:25 DAL
    14:30 MDW
    5Hrs, 05m 1 Stop (AUS)
  • DALDallas/Fort Worth Love Field Airport 09:25 - MDW 14:30 5h 05m 1 Stop (AUS) Austin
  • DALDallas/Fort Worth Love Field Airport 09:25
    AUSAustin-Bergstrom International Airport 12:00
  • AUSAustin-Bergstrom International Airport 10:25
    MDWChicago Midway Airport 14:30
  • 5h 05m (1h 35m)
  • 1 Stop AUS · Austin 1h 35m
  • Southwest Airlines (WN 4263)Boeing 737 700
    Southwest Airlines (WN 2434)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 4263)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 09:40 DAL
    14:45 MDW
    5Hrs, 05m 1 Stop (MCI)
  • DALDallas/Fort Worth Love Field Airport 09:40 - MDW 14:45 5h 05m 1 Stop (MCI) Kansas City
  • DALDallas/Fort Worth Love Field Airport 09:40
    MCIKansas City International Airport 13:20
  • MCIKansas City International Airport 11:10
    MDWChicago Midway Airport 14:45
  • 5h 05m (2h 10m)
  • 1 Stop MCI · Kansas City 2h 10m
  • Southwest Airlines (WN 4467)Boeing 737 700
    Southwest Airlines (WN 2689)Boeing 737 700
  • Southwest Airlines (WN 4467)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 09:53 DFW
    14:41 ORD
    4Hrs, 48m 1 Stop (IAH)
  • DFWDallas/Fort Worth Intl Airport 09:53 - ORD 14:41 4h 48m 1 Stop (IAH) Houston
  • DFWDallas/Fort Worth Intl Airport 09:53
    IAHHouston George Bush Intercontinental Airport 11:55
  • IAHHouston George Bush Intercontinental Airport 11:10
    ORDChicago O'Hare International Airport 14:41
  • 4h 48m (45m)
  • 1 Stop IAH · Houston 45m
  • United Airlines (UA 2675)Boeing 737 700
    United Airlines (UA 1168)Airbus A321 Neo
  • United Airlines (UA 2675)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 09:53 DFW
    14:40 ORD
    4Hrs, 47m 1 Stop (IAH)
  • DFWDallas/Fort Worth Intl Airport 09:53 - ORD 14:40 4h 47m 1 Stop (IAH) Houston
  • DFWDallas/Fort Worth Intl Airport 09:53
    IAHHouston George Bush Intercontinental Airport 12:00
  • IAHHouston George Bush Intercontinental Airport 11:10
    ORDChicago O'Hare International Airport 14:40
  • 4h 47m (50m)
  • 1 Stop IAH · Houston 50m
  • United Airlines (UA 2675)Boeing 737 700
    United Airlines (UA 1168)Boeing 777
  • United Airlines (UA 2675)
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • 10:00 DAL
    15:10 MDW
    5Hrs, 10m 1 Stop (BNA)
  • DALDallas/Fort Worth Love Field Airport 10:00 - MDW 15:10 5h 10m 1 Stop (BNA) Nashville
  • DALDallas/Fort Worth Love Field Airport 10:00
    BNANashville Airport 13:35
  • BNANashville Airport 11:40
    MDWChicago Midway Airport 15:10
  • 5h 10m (1h 55m)
  • 1 Stop BNA · Nashville 1h 55m
  • Southwest Airlines (WN 775)Boeing 737 800
    Southwest Airlines (WN 1622)Boeing 737 700
  • Southwest Airlines (WN 775)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 10:00 DAL
    14:15 MDW
    4Hrs, 15m 1 Stop (HOU)
  • DALDallas/Fort Worth Love Field Airport 10:00 - MDW 14:15 4h 15m 1 Stop (HOU) Houston
  • DALDallas/Fort Worth Love Field Airport 10:00
    HOUHouston Hobby Airport 11:50
  • HOUHouston Hobby Airport 11:10
    MDWChicago Midway Airport 14:15
  • 4h 15m (40m)
  • 1 Stop HOU · Houston 40m
  • Southwest Airlines (WN 15)Boeing 737 800
    Southwest Airlines (WN 2630)Boeing 737 800
  • Southwest Airlines (WN 15)
    • -
    • T
    • -
    • -
    • -
    • -
    • -
  • 10:00 DAL
    14:15 MDW
    4Hrs, 15m 1 Stop (HOU)
  • DALDallas/Fort Worth Love Field Airport 10:00 - MDW 14:15 4h 15m 1 Stop (HOU) Houston
  • DALDallas/Fort Worth Love Field Airport 10:00
    HOUHouston Hobby Airport 11:50
  • HOUHouston Hobby Airport 11:10
    MDWChicago Midway Airport 14:15
  • 4h 15m (40m)
  • 1 Stop HOU · Houston 40m
  • Southwest Airlines (WN 15)Boeing 737 700
    Southwest Airlines (WN 2630)Boeing 737 800
  • Southwest Airlines (WN 15)
    • -
    • -
    • W
    • -
    • -
    • -
    • -
  • 10:02 DFW
    15:11 MDW
    5Hrs, 09m 1 Stop (ATL)
  • DFWDallas/Fort Worth Intl Airport 10:02 - MDW 15:11 5h 09m 1 Stop (ATL) Atlanta
  • DFWDallas/Fort Worth Intl Airport 10:02
    ATLAtlanta Hartsfield-Jackson Intl Airport 14:13
  • ATLAtlanta Hartsfield-Jackson Intl Airport 13:13
    MDWChicago Midway Airport 15:11
  • 5h 09m (1h)
  • 1 Stop ATL · Atlanta 1h
  • Frontier Airlines (F9 3022)Airbus A320 Neo
    Frontier Airlines (F9 2779)Airbus A320 Neo
  • Frontier Airlines (F9 3022)
    • -
    • T
    • -
    • -
    • -
    • -
    • -
  • 10:07 DFW
    15:11 MDW
    5Hrs, 04m 1 Stop (ATL)
  • DFWDallas/Fort Worth Intl Airport 10:07 - MDW 15:11 5h 04m 1 Stop (ATL) Atlanta
  • DFWDallas/Fort Worth Intl Airport 10:07
    ATLAtlanta Hartsfield-Jackson Intl Airport 14:13
  • ATLAtlanta Hartsfield-Jackson Intl Airport 13:18
    MDWChicago Midway Airport 15:11
  • 5h 04m (55m)
  • 1 Stop ATL · Atlanta 55m
  • Frontier Airlines (F9 3022)Airbus A320 Neo
    Frontier Airlines (F9 2779)Airbus A320 Neo
  • Frontier Airlines (F9 3022)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 10:07 DFW
    16:07 ORD
    6Hrs, 00m 1 Stop (ATL)
  • DFWDallas/Fort Worth Intl Airport 10:07 - ORD 16:07 6h 1 Stop (ATL) Atlanta
  • DFWDallas/Fort Worth Intl Airport 10:07
    ATLAtlanta Hartsfield-Jackson Intl Airport 14:44
  • ATLAtlanta Hartsfield-Jackson Intl Airport 13:18
    ORDChicago O'Hare International Airport 16:07
  • 6h (1h 26m)
  • 1 Stop ATL · Atlanta 1h 26m
  • Frontier Airlines (F9 3022)Airbus A320 Neo
    Frontier Airlines (F9 1441)Airbus A320 Neo
  • Frontier Airlines (F9 3022)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 10:20 DAL
    16:20 MDW
    6Hrs, 00m 1 Stop (MCI)
  • DALDallas/Fort Worth Love Field Airport 10:20 - MDW 16:20 6h 1 Stop (MCI) Kansas City
  • DALDallas/Fort Worth Love Field Airport 10:20
    MCIKansas City International Airport 14:55
  • MCIKansas City International Airport 11:50
    MDWChicago Midway Airport 16:20
  • 6h (3h 05m)
  • 1 Stop MCI · Kansas City 3h 05m
  • Southwest Airlines (WN 843)Boeing 737 800
    Southwest Airlines (WN 2951)Boeing 737 700
  • Southwest Airlines (WN 843)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 10:20 DAL
    13:55 MDW
    3Hrs, 35m 1 Stop (MCI)
  • DALDallas/Fort Worth Love Field Airport 10:20 - MDW 13:55 3h 35m 1 Stop (MCI) Kansas City
  • DALDallas/Fort Worth Love Field Airport 10:20
    MCIKansas City International Airport 12:30
  • MCIKansas City International Airport 11:50
    MDWChicago Midway Airport 13:55
  • 3h 35m (40m)
  • 1 Stop MCI · Kansas City 40m
  • Southwest Airlines (WN 843)Boeing 737 800
    Southwest Airlines (WN 446)Boeing 737 700
  • Southwest Airlines (WN 843)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 10:25 DFW
    14:15 ORD
    3Hrs, 50m 1 Stop (TBN)
  • DFWDallas/Fort Worth Intl Airport 10:25 - ORD 14:15 3h 50m 1 Stop (TBN) Fort Leonard Wood
  • DFWDallas/Fort Worth Intl Airport 10:25
    TBNFort Leonard Wood Airport 12:30
  • TBNFort Leonard Wood Airport 12:00
    ORDChicago O'Hare International Airport 14:15
  • 3h 50m (30m)
  • 1 Stop TBN · Fort Leonard Wood 30m
  • Contour Airlines (LF 3552)Crj Canadair Regional
    Contour Airlines (LF 3548)Crj Canadair Regional
  • Contour Airlines (LF 3552)
    • M
    • -
    • -
    • T
    • F
    • S
    • S
  • 10:25 DAL
    15:40 MDW
    5Hrs, 15m 1 Stop (OMA)
  • DALDallas/Fort Worth Love Field Airport 10:25 - MDW 15:40 5h 15m 1 Stop (OMA) Omaha
  • DALDallas/Fort Worth Love Field Airport 10:25
    OMAOmaha Eppley Airfield Airport 14:15
  • OMAOmaha Eppley Airfield Airport 12:10
    MDWChicago Midway Airport 15:40
  • 5h 15m (2h 05m)
  • 1 Stop OMA · Omaha 2h 05m
  • Southwest Airlines (WN 2637)Boeing 737 800
    Southwest Airlines (WN 2687)Boeing 737 700
  • Southwest Airlines (WN 2637)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 10:25 DAL
    16:15 MDW
    5Hrs, 50m 1 Stop (DCA)
  • DALDallas/Fort Worth Love Field Airport 10:25 - MDW 16:15 5h 50m 1 Stop (DCA) Washington
  • DALDallas/Fort Worth Love Field Airport 10:25
    DCAWashington Ronald Reagan National Airport 15:05
  • DCAWashington Ronald Reagan National Airport 14:10
    MDWChicago Midway Airport 16:15
  • 5h 50m (55m)
  • 1 Stop DCA · Washington 55m
  • Southwest Airlines (WN 534)Boeing 737 700
    Southwest Airlines (WN 1542)Boeing 737 700
  • Southwest Airlines (WN 534)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 10:30 DAL
    15:55 MDW
    5Hrs, 25m 1 Stop (TUL)
  • DALDallas/Fort Worth Love Field Airport 10:30 - MDW 15:55 5h 25m 1 Stop (TUL)
  • DALDallas/Fort Worth Love Field Airport 10:30
    TULTulsa International Airport 14:10
  • TULTulsa International Airport 11:35
    MDWChicago Midway Airport 15:55
  • 5h 25m (2h 35m)
  • 1 Stop TUL · 2h 35m
  • Southwest Airlines (WN 431)Boeing 737 700
    Southwest Airlines (WN 2443)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 431)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 10:45 DAL
    16:05 MDW
    5Hrs, 20m 1 Stop (DEN)
  • DALDallas/Fort Worth Love Field Airport 10:45 - MDW 16:05 5h 20m 1 Stop (DEN) Denver
  • DALDallas/Fort Worth Love Field Airport 10:45
    DENDenver Intl Airport 12:50
  • DENDenver Intl Airport 11:50
    MDWChicago Midway Airport 16:05
  • 5h 20m (1h)
  • 1 Stop DEN · Denver 1h
  • Southwest Airlines (WN 2867)Boeing 737 700
    Southwest Airlines (WN 2337)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 2867)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 10:45 DAL
    16:45 ORD
    6Hrs, 00m 1 Stop (DEN)
  • DALDallas/Fort Worth Love Field Airport 10:45 - ORD 16:45 6h 1 Stop (DEN) Denver
  • DALDallas/Fort Worth Love Field Airport 10:45
    DENDenver Intl Airport 13:15
  • DENDenver Intl Airport 11:50
    ORDChicago O'Hare International Airport 16:45
  • 6h (1h 25m)
  • 1 Stop DEN · Denver 1h 25m
  • Southwest Airlines (WN 2867)Boeing 737 700
    Southwest Airlines (WN 557)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 2867)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 10:50 DAL
    14:55 MDW
    4Hrs, 05m 1 Stop (TUL)
  • DALDallas/Fort Worth Love Field Airport 10:50 - MDW 14:55 4h 05m 1 Stop (TUL)
  • DALDallas/Fort Worth Love Field Airport 10:50
    TULTulsa International Airport 13:10
  • TULTulsa International Airport 11:55
    MDWChicago Midway Airport 14:55
  • 4h 05m (1h 15m)
  • 1 Stop TUL · 1h 15m
  • Southwest Airlines (WN 3035)Boeing 737 Max 8 Passenger
    Southwest Airlines (WN 2047)Boeing 737 800
  • Southwest Airlines (WN 3035)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 10:55 DAL
    16:20 MDW
    5Hrs, 25m 1 Stop (BNA)
  • DALDallas/Fort Worth Love Field Airport 10:55 - MDW 16:20 5h 25m 1 Stop (BNA) Nashville
  • DALDallas/Fort Worth Love Field Airport 10:55
    BNANashville Airport 14:45
  • BNANashville Airport 12:40
    MDWChicago Midway Airport 16:20
  • 5h 25m (2h 05m)
  • 1 Stop BNA · Nashville 2h 05m
  • Southwest Airlines (WN 3022)Boeing 737 800
    Southwest Airlines (WN 4066)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 3022)
    • -
    • -
    • -
    • -
    • -
    • S
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  • 11:00 DAL
    16:50 MDW
    5Hrs, 50m 1 Stop (BHM)
  • DALDallas/Fort Worth Love Field Airport 11:00 - MDW 16:50 5h 50m 1 Stop (BHM) Birmingham
  • DALDallas/Fort Worth Love Field Airport 11:00
    BHMBirmingham Airport 14:55
  • BHMBirmingham Airport 12:35
    MDWChicago Midway Airport 16:50
  • 5h 50m (2h 20m)
  • 1 Stop BHM · Birmingham 2h 20m
  • Southwest Airlines (WN 3379)Boeing 737 700
    Southwest Airlines (WN 203)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 3379)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 11:00 DAL
    16:45 MDW
    5Hrs, 45m 1 Stop (DEN)
  • DALDallas/Fort Worth Love Field Airport 11:00 - MDW 16:45 5h 45m 1 Stop (DEN) Denver
  • DALDallas/Fort Worth Love Field Airport 11:00
    DENDenver Intl Airport 13:25
  • DENDenver Intl Airport 12:05
    MDWChicago Midway Airport 16:45
  • 5h 45m (1h 20m)
  • 1 Stop DEN · Denver 1h 20m
  • Southwest Airlines (WN 2347)Boeing 737 700
    Southwest Airlines (WN 1226)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 2347)
    • -
    • -
    • -
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    • -
    • S
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  • 11:05 DAL
    17:05 MDW
    6Hrs, 00m 1 Stop (TPA)
  • DALDallas/Fort Worth Love Field Airport 11:05 - MDW 17:05 6h 1 Stop (TPA) Tampa
  • DALDallas/Fort Worth Love Field Airport 11:05
    TPATampa International Airport 15:25
  • TPATampa International Airport 14:20
    MDWChicago Midway Airport 17:05
  • 6h (1h 05m)
  • 1 Stop TPA · Tampa 1h 05m
  • Southwest Airlines (WN 2279)Boeing 737 Max 8 Passenger
    Southwest Airlines (WN 3601)Boeing 737 700
  • Southwest Airlines (WN 2279)
    • -
    • -
    • -
    • -
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    • S
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  • 11:20 DAL
    16:45 MDW
    5Hrs, 25m 1 Stop (ELP)
  • DALDallas/Fort Worth Love Field Airport 11:20 - MDW 16:45 5h 25m 1 Stop (ELP) El Paso
  • DALDallas/Fort Worth Love Field Airport 11:20
    ELPEl Paso International Airport 12:45
  • ELPEl Paso International Airport 12:10
    MDWChicago Midway Airport 16:45
  • 5h 25m (35m)
  • 1 Stop ELP · El Paso 35m
  • Southwest Airlines (WN 163)Boeing 737 700
    Southwest Airlines (WN 3144)Boeing 737 700
  • Southwest Airlines (WN 163)
    • -
    • T
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  • 11:35 DAL
    17:15 MDW
    5Hrs, 40m 1 Stop (STL)
  • DALDallas/Fort Worth Love Field Airport 11:35 - MDW 17:15 5h 40m 1 Stop (STL) Saint Louis
  • DALDallas/Fort Worth Love Field Airport 11:35
    STLSt Louis Lambert Intl Airport 16:05
  • STLSt Louis Lambert Intl Airport 13:15
    MDWChicago Midway Airport 17:15
  • 5h 40m (2h 50m)
  • 1 Stop STL · Saint Louis 2h 50m
  • Southwest Airlines (WN 1321)Boeing 737 Max 8 Passenger
    Southwest Airlines (WN 2973)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 1321)
    • -
    • T
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  • 11:45 DAL
    17:35 MDW
    5Hrs, 50m 1 Stop (BNA)
  • DALDallas/Fort Worth Love Field Airport 11:45 - MDW 17:35 5h 50m 1 Stop (BNA) Nashville
  • DALDallas/Fort Worth Love Field Airport 11:45
    BNANashville Airport 16:00
  • BNANashville Airport 13:30
    MDWChicago Midway Airport 17:35
  • 5h 50m (2h 30m)
  • 1 Stop BNA · Nashville 2h 30m
  • Southwest Airlines (WN 1535)Boeing 737 800
    Southwest Airlines (WN 477)Boeing 737 800
  • Southwest Airlines (WN 1535)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
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What’s the fastest flight time from Dallas to Chicago?

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

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

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

How far is Chicago from Dallas?

The flight distance between Dallas and Chicago is 1295km. 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 18:15. See the full list of flight times on Wego.

How many airlines offer direct flights from Dallas to Chicago?

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