All airlines flying from Denver (DEN) to Chicago Midway (MDW).

FLIGHT SCHEDULE
Direct Flights:
Mon,Thu,Fri 07:10 Denver (DEN) 10:30 Chicago Midway (MDW) Southwest Airlines WN 114 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-06-04 through 2026-08-03
Sun 07:15 Denver (DEN) 10:35 Chicago Midway (MDW) Southwest Airlines WN 114 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-06-07 through 2026-08-02
Sat 07:20 Denver (DEN) 10:55 Chicago Midway (MDW) Southwest Airlines WN 127 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-02-14 through 2026-02-28
Sat 18:25 Denver (DEN) 21:55 Chicago Midway (MDW) Southwest Airlines WN 223 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-06-06 through 2026-08-01
Sun 13:45 Denver (DEN) 17:10 Chicago Midway (MDW) Southwest Airlines WN 254 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-05-24
Tue,Wed 07:40 Denver (DEN) 11:05 Chicago Midway (MDW) Southwest Airlines WN 280 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-06-09 through 2026-07-29
Tue,Wed 12:00 Denver (DEN) 15:25 Chicago Midway (MDW) Southwest Airlines WN 284 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-06-09 through 2026-07-29
Sun 07:50 Denver (DEN) 11:15 Chicago Midway (MDW) Southwest Airlines WN 482 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-04-12 through 2026-05-17
Sun 07:50 Denver (DEN) 11:15 Chicago Midway (MDW) Southwest Airlines WN 482 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-05-31
Mon,Thu,Fri 08:25 Denver (DEN) 11:50 Chicago Midway (MDW) Southwest Airlines WN 482 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-04-09 through 2026-06-01
Tue,Wed 08:35 Denver (DEN) 11:55 Chicago Midway (MDW) Southwest Airlines WN 482 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-04-07 through 2026-06-03
Sun 08:40 Denver (DEN) 12:00 Chicago Midway (MDW) Southwest Airlines WN 482 Non-stop Boeing 737-800 (73H) 2:20 Operates only on 2026-05-24
Sun 09:40 Denver (DEN) 13:05 Chicago Midway (MDW) Southwest Airlines WN 492 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-08-09 through 2026-09-27
Sun 05:20 Denver (DEN) 08:45 Chicago Midway (MDW) Southwest Airlines WN 497 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Valid until 2026-01-04
Fri 05:20 Denver (DEN) 08:45 Chicago Midway (MDW) Southwest Airlines WN 497 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Operates only on 2026-01-02
Sat 05:30 Denver (DEN) 09:00 Chicago Midway (MDW) Southwest Airlines WN 497 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Valid until 2026-01-03
Sat 06:35 Denver (DEN) 10:10 Chicago Midway (MDW) Southwest Airlines WN 563 Non-stop Boeing 737-800 (73H) 2:35 Operates only on 2026-01-10
Sat 08:20 Denver (DEN) 11:45 Chicago Midway (MDW) Southwest Airlines WN 563 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-01-17 through 2026-02-07
Mon,Thu,Fri 09:30 Denver (DEN) 12:55 Chicago Midway (MDW) Southwest Airlines WN 563 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 09:30 Denver (DEN) 12:55 Chicago Midway (MDW) Southwest Airlines WN 563 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-02-20 through 2026-03-01
Mon,Thu,Fri 11:05 Denver (DEN) 14:25 Chicago Midway (MDW) Southwest Airlines WN 563 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-02-05 through 2026-02-09
Tue,Thu,Sun 11:05 Denver (DEN) 14:25 Chicago Midway (MDW) Southwest Airlines WN 563 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-02-15 through 2026-02-19
Mon 11:05 Denver (DEN) 14:25 Chicago Midway (MDW) Southwest Airlines WN 563 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-02-23 through 2026-03-02
Sat 11:10 Denver (DEN) 14:30 Chicago Midway (MDW) Southwest Airlines WN 563 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-02-14 through 2026-02-28
Thu,Fri,Sun 11:25 Denver (DEN) 14:50 Chicago Midway (MDW) Southwest Airlines WN 563 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-01-11 through 2026-01-16
Mon,Sun 11:25 Denver (DEN) 14:50 Chicago Midway (MDW) Southwest Airlines WN 563 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-01-19 through 2026-01-25
Sun 11:25 Denver (DEN) 14:50 Chicago Midway (MDW) Southwest Airlines WN 563 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-02-01
Sat 20:20 Denver (DEN) 23:40 Chicago Midway (MDW) Southwest Airlines WN 636 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-06-06 through 2026-08-01
Mon,Thu-Sat 10:00 Denver (DEN) 13:25 Chicago Midway (MDW) Southwest Airlines WN 755 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-06-04 through 2026-08-03
Sun 10:05 Denver (DEN) 13:30 Chicago Midway (MDW) Southwest Airlines WN 755 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-06-07 through 2026-08-02
Tue,Wed 10:15 Denver (DEN) 13:50 Chicago Midway (MDW) Southwest Airlines WN 755 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-06-09 through 2026-07-29
Mon-Fri 13:25 Denver (DEN) 16:45 Chicago Midway (MDW) Southwest Airlines WN 818 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-01-06 through 2026-01-14
Tue-Fri,Sun 13:25 Denver (DEN) 16:45 Chicago Midway (MDW) Southwest Airlines WN 818 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-01-18 through 2026-01-23
Mon-Fri 13:25 Denver (DEN) 16:45 Chicago Midway (MDW) Southwest Airlines WN 818 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-01-26 through 2026-02-04
Tue,Wed,Sun 13:25 Denver (DEN) 16:45 Chicago Midway (MDW) Southwest Airlines WN 818 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-02-08 through 2026-02-11
Tue,Wed 13:25 Denver (DEN) 16:45 Chicago Midway (MDW) Southwest Airlines WN 818 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-02-18 through 2026-03-04
Thu,Fri,Sun 13:45 Denver (DEN) 17:05 Chicago Midway (MDW) Southwest Airlines WN 818 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-01-11 through 2026-01-16
Mon,Sun 13:45 Denver (DEN) 17:05 Chicago Midway (MDW) Southwest Airlines WN 818 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 13:45 Denver (DEN) 17:05 Chicago Midway (MDW) Southwest Airlines WN 818 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-02-01 through 2026-02-06
Mon,Sun 13:45 Denver (DEN) 17:05 Chicago Midway (MDW) Southwest Airlines WN 818 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 13:45 Denver (DEN) 17:05 Chicago Midway (MDW) Southwest Airlines WN 818 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-02-17 through 2026-02-23
Mon 13:45 Denver (DEN) 17:05 Chicago Midway (MDW) Southwest Airlines WN 818 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2026-03-02
Mon,Thu,Fri 07:35 Denver (DEN) 11:10 Chicago Midway (MDW) Southwest Airlines WN 1101 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-02-05 through 2026-02-09
Tue,Thu,Sun 07:35 Denver (DEN) 11:10 Chicago Midway (MDW) Southwest Airlines WN 1101 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-02-15 through 2026-02-19
Mon 07:35 Denver (DEN) 11:10 Chicago Midway (MDW) Southwest Airlines WN 1101 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-02-23 through 2026-03-02
Thu,Fri,Sun 07:40 Denver (DEN) 11:10 Chicago Midway (MDW) Southwest Airlines WN 1101 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-01-11 through 2026-01-16
Mon,Sun 07:40 Denver (DEN) 11:10 Chicago Midway (MDW) Southwest Airlines WN 1101 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-01-19 through 2026-01-25
Sun 07:40 Denver (DEN) 11:10 Chicago Midway (MDW) Southwest Airlines WN 1101 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Operates only on 2026-02-01
Sat 07:15 Denver (DEN) 10:35 Chicago Midway (MDW) Southwest Airlines WN 1183 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-06-06 through 2026-08-01
Sat 07:15 Denver (DEN) 10:35 Chicago Midway (MDW) Southwest Airlines WN 1223 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-08-08 through 2026-09-26

1 2 3 4 5 6

A domestic route departing from the Denver airport (DEN) and arriving at Chicago Midway airport (MDW).
The flight distance is 893 miles, or 1436 km.
The timezone of the departure airport is UTC-7 , and the timezone of the arrival airport is UTC-6 . Current time at the point of departure is (loading...), and (loading...) at the point of arrival. There is a (loading...) hour time difference between the airports.
For direct flights, the flight time varies between 2:15 and 2:35.

Return (MDW-DEN) flights

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All airlines flying from Denver (DEN) to Chicago Midway (MDW).

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN114

07:10

Denver (DEN)

10:30

Chicago Midway (MDW)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN114

07:15

Denver (DEN)

10:35

Chicago Midway (MDW)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN127

07:20

Denver (DEN)

10:55

Chicago Midway (MDW)

Effective 2026-02-14 through 2026-02-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN223

18:25

Denver (DEN)

21:55

Chicago Midway (MDW)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN254

13:45

Denver (DEN)

17:10

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN280

07:40

Denver (DEN)

11:05

Chicago Midway (MDW)

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN284

12:00

Denver (DEN)

15:25

Chicago Midway (MDW)

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN482

07:50

Denver (DEN)

11:15

Chicago Midway (MDW)

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN482

07:50

Denver (DEN)

11:15

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN482

08:25

Denver (DEN)

11:50

Chicago Midway (MDW)

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN482

08:35

Denver (DEN)

11:55

Chicago Midway (MDW)

Effective 2026-04-07 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN482

08:40

Denver (DEN)

12:00

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN492

09:40

Denver (DEN)

13:05

Chicago Midway (MDW)

Effective 2026-08-09 through 2026-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN497

05:20

Denver (DEN)

08:45

Chicago Midway (MDW)

Valid until 2026-01-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN497

05:20

Denver (DEN)

08:45

Chicago Midway (MDW)

Operates only on 2026-01-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN497

05:30

Denver (DEN)

09:00

Chicago Midway (MDW)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN563

06:35

Denver (DEN)

10:10

Chicago Midway (MDW)

Operates only on 2026-01-10

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:35, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN563

08:20

Denver (DEN)

11:45

Chicago Midway (MDW)

Effective 2026-01-17 through 2026-02-07

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN563

09:30

Denver (DEN)

12:55

Chicago Midway (MDW)

Effective 2026-02-12 through 2026-02-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN563

09:30

Denver (DEN)

12:55

Chicago Midway (MDW)

Effective 2026-02-20 through 2026-03-01

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN563

11:05

Denver (DEN)

14:25

Chicago Midway (MDW)

Effective 2026-02-05 through 2026-02-09

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN563

11:05

Denver (DEN)

14:25

Chicago Midway (MDW)

Effective 2026-02-15 through 2026-02-19

Mon
-

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN563

11:05

Denver (DEN)

14:25

Chicago Midway (MDW)

Effective 2026-02-23 through 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN563

11:10

Denver (DEN)

14:30

Chicago Midway (MDW)

Effective 2026-02-14 through 2026-02-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN563

11:25

Denver (DEN)

14:50

Chicago Midway (MDW)

Effective 2026-01-11 through 2026-01-16

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN563

11:25

Denver (DEN)

14:50

Chicago Midway (MDW)

Effective 2026-01-19 through 2026-01-25

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN563

11:25

Denver (DEN)

14:50

Chicago Midway (MDW)

Operates only on 2026-02-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN636

20:20

Denver (DEN)

23:40

Chicago Midway (MDW)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN755

10:00

Denver (DEN)

13:25

Chicago Midway (MDW)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN755

10:05

Denver (DEN)

13:30

Chicago Midway (MDW)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN755

10:15

Denver (DEN)

13:50

Chicago Midway (MDW)

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN818

13:25

Denver (DEN)

16:45

Chicago Midway (MDW)

Effective 2026-01-06 through 2026-01-14

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN818

13:25

Denver (DEN)

16:45

Chicago Midway (MDW)

Effective 2026-01-18 through 2026-01-23

Mon
-

Tue

Wed

Thu

Fri

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN818

13:25

Denver (DEN)

16:45

Chicago Midway (MDW)

Effective 2026-01-26 through 2026-02-04

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN818

13:25

Denver (DEN)

16:45

Chicago Midway (MDW)

Effective 2026-02-08 through 2026-02-11

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN818

13:25

Denver (DEN)

16:45

Chicago Midway (MDW)

Effective 2026-02-18 through 2026-03-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN818

13:45

Denver (DEN)

17:05

Chicago Midway (MDW)

Effective 2026-01-11 through 2026-01-16

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN818

13:45

Denver (DEN)

17:05

Chicago Midway (MDW)

Effective 2026-01-19 through 2026-01-25

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN818

13:45

Denver (DEN)

17:05

Chicago Midway (MDW)

Effective 2026-02-01 through 2026-02-06

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN818

13:45

Denver (DEN)

17:05

Chicago Midway (MDW)

Effective 2026-02-09 through 2026-02-15

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN818

13:45

Denver (DEN)

17:05

Chicago Midway (MDW)

Effective 2026-02-17 through 2026-02-23

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN818

13:45

Denver (DEN)

17:05

Chicago Midway (MDW)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1101

07:35

Denver (DEN)

11:10

Chicago Midway (MDW)

Effective 2026-02-05 through 2026-02-09

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1101

07:35

Denver (DEN)

11:10

Chicago Midway (MDW)

Effective 2026-02-15 through 2026-02-19

Mon
-

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1101

07:35

Denver (DEN)

11:10

Chicago Midway (MDW)

Effective 2026-02-23 through 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1101

07:40

Denver (DEN)

11:10

Chicago Midway (MDW)

Effective 2026-01-11 through 2026-01-16

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1101

07:40

Denver (DEN)

11:10

Chicago Midway (MDW)

Effective 2026-01-19 through 2026-01-25

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1101

07:40

Denver (DEN)

11:10

Chicago Midway (MDW)

Operates only on 2026-02-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1183

07:15

Denver (DEN)

10:35

Chicago Midway (MDW)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1223

07:15

Denver (DEN)

10:35

Chicago Midway (MDW)

Effective 2026-08-08 through 2026-09-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:20, non-stop
Boeing 737-800 (73H)

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A domestic route departing from the Denver airport (DEN) and arriving at Chicago Midway airport (MDW).
The flight distance is 893 miles, or 1436 km.
The timezone of the departure airport is UTC-7 , and the timezone of the arrival airport is UTC-6 . Current time at the point of departure is (loading...), and (loading...) at the point of arrival. There is a (loading...) hour time difference between the airports.
For direct flights, the flight time varies between 2:15 and 2:35.

Return (MDW-DEN) flights

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