Airlines with flights from Denver to Chicago

There are three airlines with scheduled flights between DEN and MDW. Southwest is the only airline with non-stop flights from Denver International to Midway International Airport and the flight time is 2 hours and 20 minutes.

Change direction

Choose airline

Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 20 minutes
  • Low-cost airline
  • Denver and Chicago are both Southwest Airlines focus cities.
  • 58 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
DEN
Direct
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN1598
05:55
06:15
06:15
05:55
05:55
05:15
----
WN114
07:10
----
----
07:10
07:10
----
07:15
WN1183
----
----
----
----
----
07:15
----
WN280
----
07:40
07:40
----
----
----
----
WN755
10:00
10:15
10:15
10:00
10:00
10:00
10:05
WN1601
13:00
----
----
13:00
13:00
----
11:50
WN284
----
12:00
12:00
----
----
----
----
WN1603
15:50
13:30
13:30
15:50
15:50
15:00
14:40
WN1604
17:35
17:20
17:20
17:35
17:35
----
17:35
WN223
----
----
----
----
----
18:25
----
WN1614
----
19:00
19:00
----
----
----
19:00
WN636
----
----
----
----
----
20:20
----
WN1615
20:50
----
----
20:50
20:50
----
20:55
SHOW RETURN SCHEDULE
CHECK PRICES FOR DEN - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Kansas City with Southwest Airlines

  • Total flight time: 3h 35m - 7h 30m.
  • Low-cost airline
  • Denver and Chicago are both Southwest Airlines focus cities.
  • 114 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
DEN
 
Via MCI
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN1584
WN1774
----
06:10
06:10
----
----
----
----
WN1584
WN2572
08:40
----
----
08:40
08:40
07:45
----
WN3114
WN2571
----
08:05
08:05
----
----
----
----
WN3114
WN2572
10:00
----
----
10:00
10:00
----
----
WN2572
WN1286
----
----
----
----
----
10:00
----
WN1586
WN2571
----
----
----
----
----
----
10:05
WN1586
WN2953
----
10:25
10:25
----
----
----
----
WN1229
WN2571
----
----
----
----
----
----
11:15
WN351
WN2478
----
12:05
12:05
----
----
----
----
WN351
WN2029
12:30
----
----
12:30
12:30
----
----
WN1587
WN2572
----
----
----
----
----
----
14:05
WN1587
WN345
15:10
----
----
15:10
15:10
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR DEN - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Milwaukee with Southwest Airlines

  • Total flight time: 3h 45m - 6h 05m.
  • Low-cost airline
  • Denver and Chicago are both Southwest Airlines focus cities.
  • 14 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
DEN
 
Via MKE
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN1626
WN2909
----
----
----
----
----
10:10
----
WN2367
WN1734
----
----
----
----
----
----
10:30
WN1626
WN2953
----
10:30
10:30
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR DEN - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Saint Louis with Southwest Airlines

  • Total flight time: 3h 50m - 7h 25m.
  • Low-cost airline
  • Denver and Chicago are both Southwest Airlines focus cities.
  • 122 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
DEN
 
Via STL
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN1751
WN1373
----
06:15
06:15
----
----
----
----
WN1373
WN3344
07:20
----
----
07:20
07:20
----
----
WN1753
WN2468
----
----
----
----
----
10:00
----
WN681
WN556
----
----
----
----
----
----
10:00
WN1753
WN556
10:05
10:20
10:20
10:05
10:05
----
----
WN5066
WN2468
----
----
----
----
----
11:15
----
WN3152
WN556
11:45
----
----
11:45
11:45
----
11:55
WN3152
WN2289
----
13:00
13:00
----
----
----
----
WN4213
WN3957
----
15:55
15:55
----
----
----
----
WN1718
WN3957
----
----
----
----
----
----
17:50
SHOW RETURN SCHEDULE
CHECK PRICES FOR DEN - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Omaha with Southwest Airlines

  • Total flight time: 3h 50m - 5h 45m.
  • Low-cost airline
  • Denver and Chicago are both Southwest Airlines focus cities.
  • 40 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
DEN
 
Via OMA
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN1655
WN4470
----
08:10
08:10
----
----
----
----
WN1123
WN280
----
----
----
----
----
10:15
----
WN748
WN4094
----
10:30
10:30
----
----
----
----
WN1705
WN4094
12:35
----
----
12:35
12:35
----
12:35
WN1658
WN5114
----
----
----
----
----
----
14:20
SHOW RETURN SCHEDULE
CHECK PRICES FOR DEN - MDW

The timetable & schedule information was updated at 2026-04-21

Change direction

Staying up-to-date with the airlines

At Airlineinformation.com you can learn all about the airlines operating around the world together with their destinations and where they operate. You will get a transparent overview of airlines with scheduled flights between any two destinations with non-stop or 1-stop flights regardless of price or availability.
Flight data on this page was last updated on 2026-06-02
© 2026 Westcoast Digital