Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from Dallas to Chicago is Frontier Airlines.
Cheapest Month
May
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
Cheapest Day of the Week
Saturday
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
Cheapest Time
10pm
The cheapest time of the day to fly from Dallas to Chicago is in the evening.
Early Morning 12:01am - 06:00am
Morning 6:01am - 12:00pm
Afternoon 12:01pm - 6:00pm
Evening 6:01pm to 12:00am
12am
6am
12pm
6pm
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
- M
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- S
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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
-
- 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
-
- -
- -
- -
- -
- -
- -
- 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
-
- 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
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
-
21:10 - 23:20DAL - MDW
-
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
-
- -
- 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
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
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05:00 - 07:28DFW - ORD
-
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
-
- 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
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
06:00 - 08:10DAL - MDW
-
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
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
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06:05 - 08:25DAL - ORD
-
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
-
06:05 - 08:25DAL - ORD
-
06:05 (DAL)Dallas/Fort Worth Love Field Airport
-
08:25 (ORD)Chicago O'Hare International Airport
-
(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
-
- 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
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
-
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
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
-
07:10 - 09:37DFW - ORD
-
07:10 (DFW)Dallas/Fort Worth Intl Airport
-
09:37 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1210)Boeing 737 800 - 2h 27m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
07:15 - 09:20DAL - MDW
-
07:15 (DAL)Dallas/Fort Worth Love Field Airport
-
09:20 (MDW)Chicago Midway Airport
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(WN 3079)Boeing 737 800 - 2h 05m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 800
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07:25 - 09:46DFW - ORD
-
07:25 (DFW)Dallas/Fort Worth Intl Airport
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09:46 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 380)Airbus - 2h 21m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
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07:30 - 09:40DAL - MDW
-
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
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
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07:35 - 09:45DAL - MDW
-
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
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
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08:25 - 10:55DFW - ORD
-
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
- -
- -
- 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
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 Max 8 Passenger
-
09:40 - 13:45DAL - MDW
-
09:40 (DAL)Dallas/Fort Worth Love Field Airport
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13:45 (MDW)Chicago Midway Airport
-
(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
-
- 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
-
United Airlines (UA 1634)Boeing 737 700 - 2h 20m
- Direct
-
- 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
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
-
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
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
-
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
-
- 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
-
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
-
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
-
11:55 - 14:10DAL - MDW
-
11:55 (DAL)Dallas/Fort Worth Love Field Airport
-
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
-
12:35 (DAL)Dallas/Fort Worth Love Field Airport
-
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
-
12:35 - 14:45DAL - MDW
-
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
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
-
12:40 - 15:00DAL - ORD
-
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
-
12:50 - 15:00DAL - MDW
-
12:50 (DAL)Dallas/Fort Worth Love Field Airport
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15:00 (MDW)Chicago Midway Airport
-
(WN 473)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 Max 8 Passenger
-
13:00 - 15:27DFW - ORD
-
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
-
(WN 473)Boeing 737 Max 8 Passenger - 2h 10m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
-
14:20 - 16:49DFW - ORD
-
14:20 (DFW)Dallas/Fort Worth Intl Airport
-
16:49 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1583)Airbus - 2h 29m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Airbus
-
14:25 - 18:20DAL - MDW
-
14:25 (DAL)Dallas/Fort Worth Love Field Airport
-
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
-
16:55 (MDW)Chicago Midway Airport
-
(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
-
(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
-
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
-
(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
-
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
-
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 Houston 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 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 Houston 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 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
- -
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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 5 minutes. Check latest flight schedules & prices 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 19:00. See the full list of flight times on Wego.
How many airlines offer direct flights from Dallas to Chicago?
There are 3 airlines that offer direct flights from Dallas to Chicago. Find out the list of airlines on Wego.
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