Fare Guide
Estimated lowest fares found within 7 days
The cheapest airline(s) flying from Dallas to Chicago is Frontier Airlines.
Travel Period: May 2024 - April 2025
The cheapest month(s) to fly from Dallas to Chicago is May.
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May 2024
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Jun 2024
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Jul 2024
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Aug 2024
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Sep 2024
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Oct 2024
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Nov 2024
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Dec 2024
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Jan 2025
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Feb 2025
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Mar 2025
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Apr 2025
The cheapest day(s) of the week to fly from Dallas to Chicago is Saturday.
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Sun Sunday
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Mon Monday
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Tue Tuesday
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Wed Wednesday
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Thu Thursday
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Fri Friday
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Sat Saturday
The cheapest time of the day to fly from Dallas to Chicago is in the evening.
Flight Schedules
Last Updated: Tue, 2 Apr, 2024
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Filter by Airline
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Total Duration
- Shortest
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Availability
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19:00 - 21:10DAL - MDW
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19:00 (DAL)Dallas/Fort Worth Love Field Airport
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21:10 (MDW)Chicago Midway Airport
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(WN 2885)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
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19:10 - 21:30DAL - ORD
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19:10 (DAL)Dallas/Fort Worth Love Field Airport
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21:30 (ORD)Chicago O'Hare International Airport
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(WN 3633)Boeing 737 700 - 2h 20m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
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20:35 - 23:12DFW - ORD
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20:35 (DFW)Dallas/Fort Worth Intl Airport
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23:12 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 2346)Boeing 737 800 - 2h 37m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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20:45 - 22:50DAL - MDW
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20:45 (DAL)Dallas/Fort Worth Love Field Airport
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22:50 (MDW)Chicago Midway Airport
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(WN 3084)Boeing 737 Max 8 Passenger - 2h 05m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
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21:10 - 23:20DAL - MDW
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21:10 (DAL)Dallas/Fort Worth Love Field Airport
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23:20 (MDW)Chicago Midway Airport
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(WN 3084)Boeing 737 800 - 2h 10m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
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22:00 - 00:10+ 1DAL - MDW
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22:00 (DAL)Dallas/Fort Worth Love Field Airport
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00:10 (MDW)Chicago Midway Airport + 1
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(WN 3084)Boeing 737 800 - 2h 10m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
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05:00 - 07:28DFW - ORD
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05:00 (DFW)Dallas/Fort Worth Intl Airport
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07:28 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1938)Airbus - 2h 28m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Airbus
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06:00 - 08:25DAL - ORD
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06:00 (DAL)Dallas/Fort Worth Love Field Airport
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08:25 (ORD)Chicago O'Hare International Airport
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(WN 574)Boeing 737 700 - 2h 25m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
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06:00 - 08:10DAL - MDW
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06:00 (DAL)Dallas/Fort Worth Love Field Airport
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08:10 (MDW)Chicago Midway Airport
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(WN 5380)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
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06:05 - 08:25DAL - ORD
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06:05 (DAL)Dallas/Fort Worth Love Field Airport
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08:25 (ORD)Chicago O'Hare International Airport
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(WN 574)Boeing 737 700 - 2h 20m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
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06:05 - 08:25DAL - ORD
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06:05 (DAL)Dallas/Fort Worth Love Field Airport
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08:25 (ORD)Chicago O'Hare International Airport
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(WN 574)Boeing 737 800 - 2h 20m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 800
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06:05 - 08:15DAL - MDW
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06:05 (DAL)Dallas/Fort Worth Love Field Airport
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08:15 (MDW)Chicago Midway Airport
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(WN 5380)Boeing 737 800 - 2h 10m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
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06:25 - 08:45DAL - ORD
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06:25 (DAL)Dallas/Fort Worth Love Field Airport
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08:45 (ORD)Chicago O'Hare International Airport
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(WN 574)Boeing 737 800 - 2h 20m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
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06:50 - 09:00DAL - MDW
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06:50 (DAL)Dallas/Fort Worth Love Field Airport
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09:00 (MDW)Chicago Midway Airport
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(WN 3079)Boeing 737 800 - 2h 10m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
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07:10 - 09:37DFW - ORD
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07:10 (DFW)Dallas/Fort Worth Intl Airport
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09:37 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1210)Boeing 737 800 - 2h 27m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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07:15 - 09:20DAL - MDW
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07:15 (DAL)Dallas/Fort Worth Love Field Airport
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09:20 (MDW)Chicago Midway Airport
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(WN 3079)Boeing 737 800 - 2h 05m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 800
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07:25 - 09:46DFW - ORD
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07:25 (DFW)Dallas/Fort Worth Intl Airport
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09:46 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 380)Airbus - 2h 21m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Airbus
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07:30 - 09:40DAL - MDW
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07:30 (DAL)Dallas/Fort Worth Love Field Airport
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09:40 (MDW)Chicago Midway Airport
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(WN 3079)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
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07:35 - 09:45DAL - MDW
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07:35 (DAL)Dallas/Fort Worth Love Field Airport
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09:45 (MDW)Chicago Midway Airport
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(WN 3079)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
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08:25 - 10:55DFW - ORD
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08:25 (DFW)Dallas/Fort Worth Intl Airport
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10:55 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 328)Airbus - 2h 30m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Airbus
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09:05 - 11:20DAL - MDW
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09:05 (DAL)Dallas/Fort Worth Love Field Airport
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11:20 (MDW)Chicago Midway Airport
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(WN 2148)Boeing 737 800 - 2h 15m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
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09:10 - 11:30DAL - ORD
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09:10 (DAL)Dallas/Fort Worth Love Field Airport
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11:30 (ORD)Chicago O'Hare International Airport
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(WN 4903)Boeing 737 800 - 2h 20m
- Direct
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- M
- -
- -
- T
- F
- -
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- Boeing 737 800
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09:30 - 13:15DAL - MDW
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09:30 (DAL)Dallas/Fort Worth Love Field Airport
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13:15 (MDW)Chicago Midway Airport
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(WN 1381)Boeing 737 700 - 3h 45m
- Direct
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- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
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09:40 - 11:50DAL - MDW
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09:40 (DAL)Dallas/Fort Worth Love Field Airport
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11:50 (MDW)Chicago Midway Airport
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(WN 2148)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
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- -
- -
- -
- -
- -
- S
- -
- Boeing 737 Max 8 Passenger
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09:40 - 13:45DAL - MDW
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09:40 (DAL)Dallas/Fort Worth Love Field Airport
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13:45 (MDW)Chicago Midway Airport
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(WN 5795)Boeing 737 700 - 4h 05m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
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10:15 - 12:40DFW - ORD
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10:15 (DFW)Dallas/Fort Worth Intl Airport
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12:40 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1805)Boeing 737 800 - 2h 25m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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10:30 - 12:50DFW - ORD
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10:30 (DFW)Dallas/Fort Worth Intl Airport
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12:50 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1634)Boeing 737 700 - 2h 20m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 700
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10:45 - 13:05DAL - ORD
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10:45 (DAL)Dallas/Fort Worth Love Field Airport
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13:05 (ORD)Chicago O'Hare International Airport
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(WN 4903)Boeing 737 700 - 2h 20m
- Direct
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- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
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11:00 - 13:10DAL - MDW
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11:00 (DAL)Dallas/Fort Worth Love Field Airport
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13:10 (MDW)Chicago Midway Airport
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(WN 2148)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
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11:05 - 15:30DAL - MDW
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11:05 (DAL)Dallas/Fort Worth Love Field Airport
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15:30 (MDW)Chicago Midway Airport
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(WN 1458)Boeing 737 700 - 4h 25m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
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11:30 - 14:00DFW - ORD
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11:30 (DFW)Dallas/Fort Worth Intl Airport
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14:00 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 2412)Airbus - 2h 30m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Airbus
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11:35 - 13:45DAL - MDW
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11:35 (DAL)Dallas/Fort Worth Love Field Airport
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13:45 (MDW)Chicago Midway Airport
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(WN 2148)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
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11:50 - 16:15DAL - MDW
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11:50 (DAL)Dallas/Fort Worth Love Field Airport
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16:15 (MDW)Chicago Midway Airport
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(WN 3052)Boeing 737 700 - 4h 25m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
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11:55 - 14:10DAL - MDW
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11:55 (DAL)Dallas/Fort Worth Love Field Airport
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14:10 (MDW)Chicago Midway Airport
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(WN 473)Boeing 737 800 - 2h 15m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
-
12:35 - 15:00DAL - ORD
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12:35 (DAL)Dallas/Fort Worth Love Field Airport
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15:00 (ORD)Chicago O'Hare International Airport
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(WN 5556)Boeing 737 800 - 2h 25m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
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12:35 - 14:45DAL - MDW
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12:35 (DAL)Dallas/Fort Worth Love Field Airport
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14:45 (MDW)Chicago Midway Airport
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(WN 473)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
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- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
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12:40 - 15:00DAL - ORD
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12:40 (DAL)Dallas/Fort Worth Love Field Airport
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15:00 (ORD)Chicago O'Hare International Airport
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(WN 4903)Boeing 737 Max 8 Passenger - 2h 20m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
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12:50 - 15:00DAL - MDW
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12:50 (DAL)Dallas/Fort Worth Love Field Airport
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15:00 (MDW)Chicago Midway Airport
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(WN 473)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 Max 8 Passenger
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13:00 - 15:27DFW - ORD
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13:00 (DFW)Dallas/Fort Worth Intl Airport
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15:27 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 2428)Airbus - 2h 27m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
-
14:00 - 16:10DAL - MDW
-
14:00 (DAL)Dallas/Fort Worth Love Field Airport
-
16:10 (MDW)Chicago Midway Airport
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(WN 473)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
-
14:20 - 16:49DFW - ORD
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14:20 (DFW)Dallas/Fort Worth Intl Airport
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16:49 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1583)Airbus - 2h 29m
- Direct
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- M
- T
- W
- T
- F
- -
- S
- Airbus
-
14:25 - 18:20DAL - MDW
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14:25 (DAL)Dallas/Fort Worth Love Field Airport
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18:20 (MDW)Chicago Midway Airport
-
(WN 950)Boeing 737 Max 8 Passenger - 3h 55m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
-
14:45 - 16:55DAL - MDW
-
14:45 (DAL)Dallas/Fort Worth Love Field Airport
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16:55 (MDW)Chicago Midway Airport
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(WN 5380)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
-
14:45 - 18:15DAL - MDW
-
14:45 (DAL)Dallas/Fort Worth Love Field Airport
-
18:15 (MDW)Chicago Midway Airport
-
(WN 2753)Boeing 737 700 - 3h 30m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
-
14:55 - 18:30DAL - MDW
-
14:55 (DAL)Dallas/Fort Worth Love Field Airport
-
18:30 (MDW)Chicago Midway Airport
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(WN 950)Boeing 737 700 - 3h 35m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
15:00 - 17:29DFW - ORD
-
15:00 (DFW)Dallas/Fort Worth Intl Airport
-
17:29 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1559)Boeing 737 800 - 2h 29m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
15:45 - 18:10DAL - ORD
-
15:45 (DAL)Dallas/Fort Worth Love Field Airport
-
18:10 (ORD)Chicago O'Hare International Airport
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(WN 3632)Boeing 737 800 - 2h 25m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
-
15:45 - 18:10DAL - ORD
-
15:45 (DAL)Dallas/Fort Worth Love Field Airport
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18:10 (ORD)Chicago O'Hare International Airport
-
(WN 3632)Boeing 737 700 - 2h 25m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
-
16:27 - 18:50DFW - ORD
-
16:27 (DFW)Dallas/Fort Worth Intl Airport
-
18:50 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1298)Airbus - 2h 23m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
-
16:30 - 18:40DAL - MDW
-
16:30 (DAL)Dallas/Fort Worth Love Field Airport
-
18:40 (MDW)Chicago Midway Airport
-
(WN 973)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
-
16:35 - 19:06DFW - ORD
-
16:35 (DFW)Dallas/Fort Worth Intl Airport
-
19:06 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1290)Boeing 737 800 - 2h 31m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
16:50 - 19:00DAL - MDW
-
16:50 (DAL)Dallas/Fort Worth Love Field Airport
-
19:00 (MDW)Chicago Midway Airport
-
(WN 973)Boeing 737 700 - 2h 10m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
17:10 - 19:20DAL - MDW
-
17:10 (DAL)Dallas/Fort Worth Love Field Airport
-
19:20 (MDW)Chicago Midway Airport
-
(WN 973)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
-
17:40 - 20:00DAL - ORD
-
17:40 (DAL)Dallas/Fort Worth Love Field Airport
-
20:00 (ORD)Chicago O'Hare International Airport
-
(WN 3633)Boeing 737 700 - 2h 20m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
18:00 - 20:24DFW - ORD
-
18:00 (DFW)Dallas/Fort Worth Intl Airport
-
20:24 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1186)Airbus - 2h 24m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
-
18:30 - 21:00DFW - ORD
-
18:30 (DFW)Dallas/Fort Worth Intl Airport
-
21:00 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 2881)Boeing 737 800 - 2h 30m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
18:30 - 20:40DAL - MDW
-
18:30 (DAL)Dallas/Fort Worth Love Field Airport
-
20:40 (MDW)Chicago Midway Airport
-
(WN 2885)Boeing 737 800 - 2h 10m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
-
18:35 - 20:55DAL - ORD
-
18:35 (DAL)Dallas/Fort Worth Love Field Airport
-
20:55 (ORD)Chicago O'Hare International Airport
-
(WN 3633)Boeing 737 700 - 2h 20m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
18:35 - 20:55DAL - ORD
-
18:35 (DAL)Dallas/Fort Worth Love Field Airport
-
20:55 (ORD)Chicago O'Hare International Airport
-
(WN 3633)Boeing 737 Max 8 Passenger - 2h 20m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
-
18:45 - 20:55DAL - MDW
-
18:45 (DAL)Dallas/Fort Worth Love Field Airport
-
20:55 (MDW)Chicago Midway Airport
-
(WN 2885)Boeing 737 800 - 2h 10m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
-
18:50 - 20:55DAL - MDW
-
18:50 (DAL)Dallas/Fort Worth Love Field Airport
-
20:55 (MDW)Chicago Midway Airport
-
(WN 2885)Boeing 737 800 - 2h 05m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 800
Connecting Flights
-
19:15 - 20:45DAL - MCI21:20 - 22:40MCI - MDW
-
19:15 (DAL)Dallas/Fort Worth Love Field Airport21:20 (MCI)Kansas City International Airport
-
20:45 (MCI)Kansas City International Airport22:40 (MDW)Chicago Midway Airport
-
(WN 1290)Boeing 737 700 (WN 282)Boeing 737 700 - 3h 25m (35m)
- MCI Kansas City 35m
-
- M
- -
- -
- T
- F
- -
- -
-
19:20 - 20:50DAL - MCI21:30 - 22:50MCI - MDW
-
19:20 (DAL)Dallas/Fort Worth Love Field Airport21:30 (MCI)Kansas City International Airport
-
20:50 (MCI)Kansas City International Airport22:50 (MDW)Chicago Midway Airport
-
(WN 519)Boeing 737 700 (WN 3312)Boeing 737 700 - 3h 30m (40m)
- MCI Kansas City 40m
-
- -
- -
- -
- -
- -
- -
- S
-
19:35 - 20:55DAL - MSY21:30 - 23:45MSY - MDW
-
19:35 (DAL)Dallas/Fort Worth Love Field Airport21:30 (MSY)New Orleans Louis Armstrong Intl Airport
-
20:55 (MSY)New Orleans Louis Armstrong Intl Airport23:45 (MDW)Chicago Midway Airport
-
(WN 1411)Boeing 737 700 (WN 4143)Boeing 737 800 - 4h 10m (35m)
- MSY New Orleans 35m
-
- -
- -
- -
- -
- -
- -
- S
-
06:00 - 09:00DAL - ATL09:50 - 10:45ATL - MDW
-
06:00 (DAL)Dallas/Fort Worth Love Field Airport09:50 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
09:00 (ATL)Atlanta Hartsfield-Jackson Intl Airport10:45 (MDW)Chicago Midway Airport
-
(WN 194)Boeing 737 Max 8 Passenger (WN 5518)Boeing 737 Max 8 Passenger - 4h 45m (50m)
- ATL Atlanta 50m
-
- -
- -
- -
- -
- -
- -
- S
-
06:00 - 07:05DAL - HOU08:35 - 11:10HOU - MDW
-
06:00 (DAL)Dallas/Fort Worth Love Field Airport08:35 (HOU)Houston Hobby Airport
-
07:05 (HOU)Houston Hobby Airport11:10 (MDW)Chicago Midway Airport
-
(WN 1628)Boeing 737 Max 8 Passenger (WN 6128)Boeing 737 700 - 5h 10m (1h 30m)
- HOU Houston 1h 30m
-
- -
- T
- W
- -
- -
- -
- -
-
06:00 - 07:10DAL - HOU08:20 - 11:00HOU - MDW
-
06:00 (DAL)Dallas/Fort Worth Love Field Airport08:20 (HOU)Houston Hobby Airport
-
07:10 (HOU)Houston Hobby Airport11:00 (MDW)Chicago Midway Airport
-
(WN 1628)Boeing 737 800 (WN 6128)Boeing 737 800 - 5h (1h 10m)
- HOU Houston 1h 10m
-
- M
- -
- -
- T
- F
- -
- -
-
06:00 - 07:00DAL - DEN08:25 - 11:50DEN - ORD
-
06:00 (DAL)Dallas/Fort Worth Love Field Airport08:25 (DEN)Denver Intl Airport
-
07:00 (DEN)Denver Intl Airport11:50 (ORD)Chicago O'Hare International Airport
-
(WN 737)Boeing 737 800 (WN 941)Boeing 737 700 - 5h 50m (1h 25m)
- DEN Denver 1h 25m
-
- -
- T
- W
- -
- -
- -
- -
-
06:00 - 07:25DAL - MCI10:20 - 11:45MCI - MDW
-
06:00 (DAL)Dallas/Fort Worth Love Field Airport10:20 (MCI)Kansas City International Airport
-
07:25 (MCI)Kansas City International Airport11:45 (MDW)Chicago Midway Airport
-
(WN 2824)Boeing 737 800 (WN 4988)Boeing 737 700 - 5h 45m (2h 55m)
- MCI Kansas City 2h 55m
-
- -
- T
- W
- -
- -
- -
- -
-
06:00 - 07:35DAL - STL10:00 - 11:05STL - MDW
-
06:00 (DAL)Dallas/Fort Worth Love Field Airport10:00 (STL)St Louis Lambert Intl Airport
-
07:35 (STL)St Louis Lambert Intl Airport11:05 (MDW)Chicago Midway Airport
-
(WN 4625)Boeing 737 700 (WN 5866)Boeing 737 Max 8 Passenger - 5h 05m (2h 25m)
- STL Saint Louis 2h 25m
-
- -
- -
- -
- -
- -
- -
- S
-
06:00 - 07:40DAL - STL09:45 - 10:50STL - MDW
-
06:00 (DAL)Dallas/Fort Worth Love Field Airport09:45 (STL)St Louis Lambert Intl Airport
-
07:40 (STL)St Louis Lambert Intl Airport10:50 (MDW)Chicago Midway Airport
-
(WN 4625)Boeing 737 800 (WN 4631)Boeing 737 700 - 4h 50m (2h 05m)
- STL Saint Louis 2h 05m
-
- -
- T
- W
- -
- -
- -
- -
-
06:00 - 07:25DAL - MCI08:15 - 09:35MCI - MDW
-
06:00 (DAL)Dallas/Fort Worth Love Field Airport08:15 (MCI)Kansas City International Airport
-
07:25 (MCI)Kansas City International Airport09:35 (MDW)Chicago Midway Airport
-
(WN 2824)Boeing 737 800 (WN 559)Boeing 737 Max 8 Passenger - 3h 35m (50m)
- MCI Kansas City 50m
-
- -
- T
- W
- -
- -
- -
- -
-
06:00 - 09:05DAL - ATL10:45 - 11:40ATL - MDW
-
06:00 (DAL)Dallas/Fort Worth Love Field Airport10:45 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
09:05 (ATL)Atlanta Hartsfield-Jackson Intl Airport11:40 (MDW)Chicago Midway Airport
-
(WN 194)Boeing 737 700 (WN 5518)Boeing 737 Max 8 Passenger - 5h 40m (1h 40m)
- ATL Atlanta 1h 40m
-
- M
- -
- -
- T
- F
- -
- -
-
06:15 - 07:15DAL - DEN08:45 - 12:00DEN - MDW
-
06:15 (DAL)Dallas/Fort Worth Love Field Airport08:45 (DEN)Denver Intl Airport
-
07:15 (DEN)Denver Intl Airport12:00 (MDW)Chicago Midway Airport
-
(WN 2350)Boeing 737 700 (WN 2503)Boeing 737 800 - 5h 45m (1h 30m)
- DEN Denver 1h 30m
-
- -
- -
- -
- -
- -
- -
- S
-
06:40 - 09:40DAL - ATL10:40 - 11:35ATL - MDW
-
06:40 (DAL)Dallas/Fort Worth Love Field Airport10:40 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
09:40 (ATL)Atlanta Hartsfield-Jackson Intl Airport11:35 (MDW)Chicago Midway Airport
-
(WN 194)Boeing 737 800 (WN 5518)Boeing 737 Max 8 Passenger - 4h 55m (1h)
- ATL Atlanta 1h
-
- -
- -
- -
- -
- -
- S
- -
-
06:45 - 07:55DAL - HOU08:55 - 11:30HOU - MDW
-
06:45 (DAL)Dallas/Fort Worth Love Field Airport08:55 (HOU)Houston Hobby Airport
-
07:55 (HOU)Houston Hobby Airport11:30 (MDW)Chicago Midway Airport
-
(WN 1628)Boeing 737 700 (WN 6128)Boeing 737 700 - 4h 45m (1h)
- HOU Houston 1h
-
- -
- -
- -
- -
- -
- -
- S
-
07:00 - 07:55DAL - AUS09:05 - 11:35AUS - MDW
-
07:00 (DAL)Dallas/Fort Worth Love Field Airport09:05 (AUS)Austin-Bergstrom International Airport
-
07:55 (AUS)Austin-Bergstrom International Airport11:35 (MDW)Chicago Midway Airport
-
(WN 372)Boeing 737 700 (WN 3033)Boeing 737 700 - 4h 35m (1h 10m)
- AUS Austin 1h 10m
-
- -
- -
- -
- -
- -
- -
- S
-
07:15 - 08:35DAL - MSY10:10 - 12:30MSY - MDW
-
07:15 (DAL)Dallas/Fort Worth Love Field Airport10:10 (MSY)New Orleans Louis Armstrong Intl Airport
-
08:35 (MSY)New Orleans Louis Armstrong Intl Airport12:30 (MDW)Chicago Midway Airport
-
(WN 6136)Boeing 737 700 (WN 1704)Boeing 737 700 - 5h 15m (1h 35m)
- MSY New Orleans 1h 35m
-
- -
- -
- -
- -
- -
- S
- -
-
07:15 - 09:00DAL - BNA11:00 - 12:45BNA - ORD
-
07:15 (DAL)Dallas/Fort Worth Love Field Airport11:00 (BNA)Nashville Airport
-
09:00 (BNA)Nashville Airport12:45 (ORD)Chicago O'Hare International Airport
-
(WN 550)Boeing 737 Max 8 Passenger (WN 3624)Boeing 737 800 - 5h 30m (2h)
- BNA Nashville 2h
-
- -
- -
- -
- -
- -
- -
- S
-
07:15 - 08:20DAL - IAH09:05 - 11:25IAH - MDW
-
07:15 (DAL)Dallas/Fort Worth Love Field Airport09:05 (IAH)Houston George Bush Intercontinental Airport
-
08:20 (IAH)Houston George Bush Intercontinental Airport11:25 (MDW)Chicago Midway Airport
-
(WN 2233)Boeing 737 Max 8 Passenger (WN 3116)Boeing 737 Max 8 Passenger - 4h 10m (45m)
- IAH 45m
-
- M
- -
- -
- T
- F
- -
- -
-
07:25 - 10:45DAL - TPA11:20 - 13:00TPA - MDW
-
07:25 (DAL)Dallas/Fort Worth Love Field Airport11:20 (TPA)Tampa International Airport
-
10:45 (TPA)Tampa International Airport13:00 (MDW)Chicago Midway Airport
-
(WN 4754)Boeing 737 700 (WN 3493)Boeing 737 Max 8 Passenger - 5h 35m (35m)
- TPA Tampa 35m
-
- -
- T
- W
- -
- -
- -
- -
-
07:30 - 09:15DAL - BNA10:15 - 12:00BNA - ORD
-
07:30 (DAL)Dallas/Fort Worth Love Field Airport10:15 (BNA)Nashville Airport
-
09:15 (BNA)Nashville Airport12:00 (ORD)Chicago O'Hare International Airport
-
(WN 550)Boeing 737 Max 8 Passenger (WN 3624)Boeing 737 700 - 4h 30m (1h)
- BNA Nashville 1h
-
- -
- -
- -
- -
- -
- S
- -
-
07:45 - 08:45DAL - AUS11:10 - 13:40AUS - MDW
-
07:45 (DAL)Dallas/Fort Worth Love Field Airport11:10 (AUS)Austin-Bergstrom International Airport
-
08:45 (AUS)Austin-Bergstrom International Airport13:40 (MDW)Chicago Midway Airport
-
(WN 462)Boeing 737 700 (WN 3033)Boeing 737 800 - 5h 55m (2h 25m)
- AUS Austin 2h 25m
-
- M
- -
- -
- T
- F
- -
- -
-
07:45 - 08:45DAL - AUS10:05 - 12:45AUS - ORD
-
07:45 (DAL)Dallas/Fort Worth Love Field Airport10:05 (AUS)Austin-Bergstrom International Airport
-
08:45 (AUS)Austin-Bergstrom International Airport12:45 (ORD)Chicago O'Hare International Airport
-
(WN 462)Boeing 737 700 (WN 5783)Boeing 737 700 - 5h (1h 20m)
- AUS Austin 1h 20m
-
- M
- -
- -
- T
- F
- -
- -
-
07:50 - 09:30DAL - STL12:35 - 13:40STL - MDW
-
07:50 (DAL)Dallas/Fort Worth Love Field Airport12:35 (STL)St Louis Lambert Intl Airport
-
09:30 (STL)St Louis Lambert Intl Airport13:40 (MDW)Chicago Midway Airport
-
(WN 5271)Boeing 737 700 (WN 3241)Boeing 737 700 - 5h 50m (3h 05m)
- STL Saint Louis 3h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
07:55 - 09:00DAL - DEN10:35 - 13:55DEN - MDW
-
07:55 (DAL)Dallas/Fort Worth Love Field Airport10:35 (DEN)Denver Intl Airport
-
09:00 (DEN)Denver Intl Airport13:55 (MDW)Chicago Midway Airport
-
(WN 1585)Boeing 737 800 (WN 878)Boeing 737 700 - 6h (1h 35m)
- DEN Denver 1h 35m
-
- -
- -
- -
- -
- -
- -
- S
-
08:00 - 09:00DAL - AUS10:05 - 12:45AUS - ORD
-
08:00 (DAL)Dallas/Fort Worth Love Field Airport10:05 (AUS)Austin-Bergstrom International Airport
-
09:00 (AUS)Austin-Bergstrom International Airport12:45 (ORD)Chicago O'Hare International Airport
-
(WN 462)Boeing 737 700 (WN 5783)Boeing 737 800 - 4h 45m (1h 05m)
- AUS Austin 1h 05m
-
- -
- T
- W
- -
- -
- -
- -
-
08:00 - 09:00DAL - AUS10:50 - 13:20AUS - MDW
-
08:00 (DAL)Dallas/Fort Worth Love Field Airport10:50 (AUS)Austin-Bergstrom International Airport
-
09:00 (AUS)Austin-Bergstrom International Airport13:20 (MDW)Chicago Midway Airport
-
(WN 462)Boeing 737 700 (WN 3033)Boeing 737 700 - 5h 20m (1h 50m)
- AUS Austin 1h 50m
-
- -
- T
- W
- -
- -
- -
- -
-
08:05 - 11:05DAL - ATL13:00 - 13:55ATL - MDW
-
08:05 (DAL)Dallas/Fort Worth Love Field Airport13:00 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
11:05 (ATL)Atlanta Hartsfield-Jackson Intl Airport13:55 (MDW)Chicago Midway Airport
-
(WN 2530)Boeing 737 Max 8 Passenger (WN 1751)Boeing 737 Max 8 Passenger - 5h 50m (1h 55m)
- ATL Atlanta 1h 55m
-
- -
- -
- -
- -
- -
- -
- S
-
08:15 - 09:20DAL - DEN10:25 - 13:40DEN - MDW
-
08:15 (DAL)Dallas/Fort Worth Love Field Airport10:25 (DEN)Denver Intl Airport
-
09:20 (DEN)Denver Intl Airport13:40 (MDW)Chicago Midway Airport
-
(WN 2566)Boeing 737 800 (WN 2503)Boeing 737 800 - 5h 25m (1h 05m)
- DEN Denver 1h 05m
-
- -
- T
- W
- -
- -
- -
- -
-
08:15 - 09:45DAL - MCI11:15 - 12:35MCI - MDW
-
08:15 (DAL)Dallas/Fort Worth Love Field Airport11:15 (MCI)Kansas City International Airport
-
09:45 (MCI)Kansas City International Airport12:35 (MDW)Chicago Midway Airport
-
(WN 4972)Boeing 737 700 (WN 4988)Boeing 737 700 - 4h 20m (1h 30m)
- MCI Kansas City 1h 30m
-
- -
- -
- -
- -
- -
- S
- -
-
08:25 - 10:10DAL - BNA11:00 - 12:45BNA - ORD
-
08:25 (DAL)Dallas/Fort Worth Love Field Airport11:00 (BNA)Nashville Airport
-
10:10 (BNA)Nashville Airport12:45 (ORD)Chicago O'Hare International Airport
-
(WN 3402)Boeing 737 700 (WN 3624)Boeing 737 800 - 4h 20m (50m)
- BNA Nashville 50m
-
- -
- -
- -
- -
- -
- -
- S
-
08:25 - 09:30DAL - DEN10:35 - 14:00DEN - ORD
-
08:25 (DAL)Dallas/Fort Worth Love Field Airport10:35 (DEN)Denver Intl Airport
-
09:30 (DEN)Denver Intl Airport14:00 (ORD)Chicago O'Hare International Airport
-
(WN 2566)Boeing 737 800 (WN 2315)Boeing 737 800 - 5h 35m (1h 05m)
- DEN Denver 1h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
08:30 - 09:40DAL - HOU11:40 - 14:10HOU - MDW
-
08:30 (DAL)Dallas/Fort Worth Love Field Airport11:40 (HOU)Houston Hobby Airport
-
09:40 (HOU)Houston Hobby Airport14:10 (MDW)Chicago Midway Airport
-
(WN 7)Boeing 737 700 (WN 460)Boeing 737 700 - 5h 40m (2h)
- HOU Houston 2h
-
- M
- -
- -
- T
- F
- -
- -
-
08:30 - 12:00DAL - MCO12:40 - 14:25MCO - MDW
-
08:30 (DAL)Dallas/Fort Worth Love Field Airport12:40 (MCO)Orlando International Airport
-
12:00 (MCO)Orlando International Airport14:25 (MDW)Chicago Midway Airport
-
(WN 2836)Boeing 737 800 (WN 3157)Boeing 737 Max 8 Passenger - 5h 55m (40m)
- MCO Orlando 40m
-
- -
- -
- -
- -
- -
- S
- -
-
08:45 - 10:15DAL - MCI12:25 - 13:45MCI - MDW
-
08:45 (DAL)Dallas/Fort Worth Love Field Airport12:25 (MCI)Kansas City International Airport
-
10:15 (MCI)Kansas City International Airport13:45 (MDW)Chicago Midway Airport
-
(WN 2703)Boeing 737 Max 8 Passenger (WN 4988)Boeing 737 800 - 5h (2h 10m)
- MCI Kansas City 2h 10m
-
- -
- -
- -
- -
- -
- -
- S
-
08:50 - 12:45DAL - BWI13:45 - 14:45BWI - MDW
-
08:50 (DAL)Dallas/Fort Worth Love Field Airport13:45 (BWI)Baltimore Washington International Airport
-
12:45 (BWI)Baltimore Washington International Airport14:45 (MDW)Chicago Midway Airport
-
(WN 5205)Boeing 737 Max 8 Passenger (WN 5950)Boeing 737 800 - 5h 55m (1h)
- BWI Baltimore 1h
-
- M
- -
- -
- T
- F
- -
- -
-
09:00 - 10:40DAL - OMA11:40 - 13:05OMA - MDW
-
09:00 (DAL)Dallas/Fort Worth Love Field Airport11:40 (OMA)Omaha Eppley Airfield Airport
-
10:40 (OMA)Omaha Eppley Airfield Airport13:05 (MDW)Chicago Midway Airport
-
(WN 493)Boeing 737 800 (WN 4380)Boeing 737 700 - 4h 05m (1h)
- OMA Omaha 1h
-
- -
- T
- W
- -
- -
- -
- -
-
09:05 - 10:35DAL - MCI12:15 - 13:40MCI - MDW
-
09:05 (DAL)Dallas/Fort Worth Love Field Airport12:15 (MCI)Kansas City International Airport
-
10:35 (MCI)Kansas City International Airport13:40 (MDW)Chicago Midway Airport
-
(WN 4972)Boeing 737 Max 8 Passenger (WN 5424)Boeing 737 700 - 4h 35m (1h 40m)
- MCI Kansas City 1h 40m
-
- M
- -
- -
- T
- F
- -
- -
-
09:20 - 11:05DAL - BNA12:30 - 14:15BNA - ORD
-
09:20 (DAL)Dallas/Fort Worth Love Field Airport12:30 (BNA)Nashville Airport
-
11:05 (BNA)Nashville Airport14:15 (ORD)Chicago O'Hare International Airport
-
(WN 551)Boeing 737 Max 8 Passenger (WN 3623)Boeing 737 700 - 4h 55m (1h 25m)
- BNA Nashville 1h 25m
-
- M
- -
- -
- T
- F
- -
- -
-
09:25 - 10:25DAL - AUS11:10 - 13:40AUS - MDW
-
09:25 (DAL)Dallas/Fort Worth Love Field Airport11:10 (AUS)Austin-Bergstrom International Airport
-
10:25 (AUS)Austin-Bergstrom International Airport13:40 (MDW)Chicago Midway Airport
-
(WN 374)Boeing 737 Max 8 Passenger (WN 3033)Boeing 737 800 - 4h 15m (45m)
- AUS Austin 45m
-
- M
- -
- -
- T
- F
- -
- -
-
09:25 - 10:55DAL - MCI13:10 - 14:30MCI - MDW
-
09:25 (DAL)Dallas/Fort Worth Love Field Airport13:10 (MCI)Kansas City International Airport
-
10:55 (MCI)Kansas City International Airport14:30 (MDW)Chicago Midway Airport
-
(WN 2703)Boeing 737 700 (WN 5424)Boeing 737 Max 8 Passenger - 5h 05m (2h 15m)
- MCI Kansas City 2h 15m
-
- -
- T
- W
- -
- -
- -
- -
-
10:00 - 11:05DAL - IAH12:40 - 15:05IAH - MDW
-
10:00 (DAL)Dallas/Fort Worth Love Field Airport12:40 (IAH)Houston George Bush Intercontinental Airport
-
11:05 (IAH)Houston George Bush Intercontinental Airport15:05 (MDW)Chicago Midway Airport
-
(WN 5795)Boeing 737 700 (WN 549)Boeing 737 700 - 5h 05m (1h 35m)
- IAH 1h 35m
-
- -
- -
- -
- -
- -
- S
- -
-
10:10 - 11:10DAL - AUS13:05 - 15:35AUS - MDW
-
10:10 (DAL)Dallas/Fort Worth Love Field Airport13:05 (AUS)Austin-Bergstrom International Airport
-
11:10 (AUS)Austin-Bergstrom International Airport15:35 (MDW)Chicago Midway Airport
-
(WN 1324)Boeing 737 700 (WN 2496)Boeing 737 Max 8 Passenger - 5h 25m (1h 55m)
- AUS Austin 1h 55m
-
- -
- -
- -
- -
- -
- -
- S
-
10:15 - 12:00DAL - BNA12:55 - 14:30BNA - MDW
-
10:15 (DAL)Dallas/Fort Worth Love Field Airport12:55 (BNA)Nashville Airport
-
12:00 (BNA)Nashville Airport14:30 (MDW)Chicago Midway Airport
-
(WN 551)Boeing 737 800 (WN 5597)Boeing 737 800 - 4h 15m (55m)
- BNA Nashville 55m
-
- -
- -
- -
- -
- -
- S
- -
-
10:25 - 13:30DAL - ATL14:10 - 15:05ATL - MDW
-
10:25 (DAL)Dallas/Fort Worth Love Field Airport14:10 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
13:30 (ATL)Atlanta Hartsfield-Jackson Intl Airport15:05 (MDW)Chicago Midway Airport
-
(WN 2530)Boeing 737 Max 8 Passenger (WN 1751)Boeing 737 800 - 4h 40m (40m)
- ATL Atlanta 40m
-
- -
- -
- -
- -
- -
- S
- -
-
10:30 - 11:30DAL - AUS13:25 - 16:00AUS - MDW
-
10:30 (DAL)Dallas/Fort Worth Love Field Airport13:25 (AUS)Austin-Bergstrom International Airport
-
11:30 (AUS)Austin-Bergstrom International Airport16:00 (MDW)Chicago Midway Airport
-
(WN 372)Boeing 737 Max 8 Passenger (WN 2496)Boeing 737 800 - 5h 30m (1h 55m)
- AUS Austin 1h 55m
-
- -
- -
- -
- -
- -
- S
- -
-
10:50 - 12:35DAL - OMA14:45 - 16:10OMA - MDW
-
10:50 (DAL)Dallas/Fort Worth Love Field Airport14:45 (OMA)Omaha Eppley Airfield Airport
-
12:35 (OMA)Omaha Eppley Airfield Airport16:10 (MDW)Chicago Midway Airport
-
(WN 2368)Boeing 737 700 (WN 298)Boeing 737 800 - 5h 20m (2h 10m)
- OMA Omaha 2h 10m
-
- -
- -
- -
- -
- -
- S
- -
-
10:55 - 12:35DAL - STL13:15 - 14:20STL - MDW
-
10:55 (DAL)Dallas/Fort Worth Love Field Airport13:15 (STL)St Louis Lambert Intl Airport
-
12:35 (STL)St Louis Lambert Intl Airport14:20 (MDW)Chicago Midway Airport
-
(WN 2210)Boeing 737 Max 8 Passenger (WN 3242)Boeing 737 700 - 3h 25m (40m)
- STL Saint Louis 40m
-
- -
- -
- -
- -
- -
- S
- -
-
11:10 - 14:05DAL - SDF16:30 - 16:45SDF - MDW
-
11:10 (DAL)Dallas/Fort Worth Love Field Airport16:30 (SDF)Louisville International Airport
-
14:05 (SDF)Louisville International Airport16:45 (MDW)Chicago Midway Airport
-
(WN 4034)Boeing 737 700 (WN 4247)Boeing 737 Max 8 Passenger - 5h 35m (2h 25m)
- SDF Louisville 2h 25m
-
- -
- -
- -
- -
- -
- S
- -
-
11:10 - 12:20DAL - HOU14:15 - 16:40HOU - MDW
-
11:10 (DAL)Dallas/Fort Worth Love Field Airport14:15 (HOU)Houston Hobby Airport
-
12:20 (HOU)Houston Hobby Airport16:40 (MDW)Chicago Midway Airport
-
(WN 19)Boeing 737 700 (WN 3970)Boeing 737 700 - 5h 30m (1h 55m)
- HOU Houston 1h 55m
-
- -
- -
- -
- -
- -
- S
- -
The fastest flight time for direct flights from Dallas to Chicago is 2 hours 5 minutes. Check latest flight schedules & prices on Wego.
The flight distance between Dallas and Chicago is 1295km. Check all available flights on Wego.
The earliest flight of the day departs at 05:00. The last flight of the day departs at 19:00. See the full list of flight times on Wego.
There are 3 airlines that offer direct flights from Dallas to Chicago. Find out the list of airlines on Wego.
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