All airlines flying from Colorado Springs (COS) to Midway, Chicago (MDW).

FLIGHT SCHEDULE
Direct Flights:
Sun 13:30 Colorado Springs (COS) 16:50 Midway, Chicago (MDW) Southwest Airlines WN 158 Non-stop Boeing 737-700 (73W) 2:20 Operates only on 2025-05-25
Sat 08:20 Colorado Springs (COS) 11:40 Midway, Chicago (MDW) Southwest Airlines WN 1823 Non-stop Boeing 737-800 (73H) 2:20 Effective 2025-08-09 through 2025-09-27
Mon,Thu,Fri 09:45 Colorado Springs (COS) 13:10 Midway, Chicago (MDW) Southwest Airlines WN 1823 Non-stop Boeing 737-700 (73W) 2:25 Effective 2025-08-07 through 2025-09-29
Tue,Wed 11:55 Colorado Springs (COS) 15:15 Midway, Chicago (MDW) Southwest Airlines WN 1823 Non-stop Boeing 737-800 (73H) 2:20 Effective 2025-08-05 through 2025-10-01
Sat 11:10 Colorado Springs (COS) 14:35 Midway, Chicago (MDW) Southwest Airlines WN 2082 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-11-22 through 2025-11-29
Sat 11:10 Colorado Springs (COS) 14:35 Midway, Chicago (MDW) Southwest Airlines WN 2082 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2025-12-20 through 2026-01-03
Mon,Thu,Fri,Sun 15:10 Colorado Springs (COS) 18:30 Midway, Chicago (MDW) Southwest Airlines WN 2082 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 15:10 Colorado Springs (COS) 18:30 Midway, Chicago (MDW) Southwest Airlines WN 2082 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2025-11-21 through 2025-11-28
Fri,Sun 15:10 Colorado Springs (COS) 18:30 Midway, Chicago (MDW) Southwest Airlines WN 2082 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2025-12-07 through 2025-12-14
Thu 15:10 Colorado Springs (COS) 18:30 Midway, Chicago (MDW) Southwest Airlines WN 2082 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Operates only on 2025-12-18
Mon 15:10 Colorado Springs (COS) 18:30 Midway, Chicago (MDW) Southwest Airlines WN 2082 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Operates only on 2026-01-05
Mon-Wed 15:25 Colorado Springs (COS) 18:50 Midway, Chicago (MDW) Southwest Airlines WN 2082 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 15:25 Colorado Springs (COS) 18:50 Midway, Chicago (MDW) Southwest Airlines WN 2082 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-12-19 through 2026-01-04
Sun 16:30 Colorado Springs (COS) 19:45 Midway, Chicago (MDW) Southwest Airlines WN 2082 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Operates only on 2025-11-30
Sat 08:25 Colorado Springs (COS) 11:50 Midway, Chicago (MDW) Southwest Airlines WN 2108 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-10-04 through 2025-11-01
Sun 11:45 Colorado Springs (COS) 15:10 Midway, Chicago (MDW) Southwest Airlines WN 2108 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2025-10-05 through 2025-10-26
Tue,Wed 13:55 Colorado Springs (COS) 17:15 Midway, Chicago (MDW) Southwest Airlines WN 2108 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2025-10-07 through 2025-10-29
Mon,Thu,Fri 14:10 Colorado Springs (COS) 17:30 Midway, Chicago (MDW) Southwest Airlines WN 2108 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2025-10-02 through 2025-10-31
Mon,Thu,Fri 09:55 Colorado Springs (COS) 13:20 Midway, Chicago (MDW) Southwest Airlines WN 2127 Non-stop Boeing 737-700 (73W) 2:25 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 09:55 Colorado Springs (COS) 13:20 Midway, Chicago (MDW) Southwest Airlines WN 2127 Non-stop Boeing 737-700 (73W) 2:25 Effective 2025-07-07 through 2025-08-04
Fri 10:05 Colorado Springs (COS) 13:25 Midway, Chicago (MDW) Southwest Airlines WN 2127 Non-stop Boeing 737-800 (73H) 2:20 Operates only on 2025-07-04
Sat 12:05 Colorado Springs (COS) 15:30 Midway, Chicago (MDW) Southwest Airlines WN 2127 Non-stop Boeing 737-800 (73H) 2:25 Effective 2025-06-07 through 2025-08-02
Tue,Wed 14:55 Colorado Springs (COS) 18:15 Midway, Chicago (MDW) Southwest Airlines WN 2127 Non-stop Boeing 737-800 (73H) 2:20 Effective 2025-06-10 through 2025-07-30
Sun 13:40 Colorado Springs (COS) 17:00 Midway, Chicago (MDW) Southwest Airlines WN 2272 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2025-08-31
Fri 14:40 Colorado Springs (COS) 18:00 Midway, Chicago (MDW) Southwest Airlines WN 2340 Non-stop Boeing 737-700 (73W) 2:20 Operates only on 2025-07-04
Sun 16:40 Colorado Springs (COS) 20:00 Midway, Chicago (MDW) Southwest Airlines WN 2413 Non-stop Boeing 737-800 (73H) 2:20 Effective 2025-06-08 through 2025-08-03
Tue,Wed 10:05 Colorado Springs (COS) 13:25 Midway, Chicago (MDW) Southwest Airlines WN 2681 Non-stop Boeing 737-700 (73W) 2:20 Effective 2025-06-10 through 2025-07-30
Mon,Thu,Fri 15:50 Colorado Springs (COS) 19:15 Midway, Chicago (MDW) Southwest Airlines WN 2681 Non-stop Boeing 737-700 (73W) 2:25 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 15:50 Colorado Springs (COS) 19:15 Midway, Chicago (MDW) Southwest Airlines WN 2681 Non-stop Boeing 737-700 (73W) 2:25 Effective 2025-07-07 through 2025-08-04
Tue,Wed 13:50 Colorado Springs (COS) 17:10 Midway, Chicago (MDW) Southwest Airlines WN 3234 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Valid until 2025-06-04
Mon,Thu,Fri 14:10 Colorado Springs (COS) 17:30 Midway, Chicago (MDW) Southwest Airlines WN 3234 Non-stop Boeing 737-700 (73W) 2:20 Valid until 2025-06-02
Sun 15:55 Colorado Springs (COS) 19:20 Midway, Chicago (MDW) Southwest Airlines WN 3661 Non-stop Boeing 737-700 (73W) 2:25 Valid until 2025-05-18
Sun 15:55 Colorado Springs (COS) 19:20 Midway, Chicago (MDW) Southwest Airlines WN 3661 Non-stop Boeing 737-700 (73W) 2:25 Operates only on 2025-06-01
Sun 11:25 Colorado Springs (COS) 14:50 Midway, Chicago (MDW) Southwest Airlines WN 4025 Non-stop Boeing 737-700 (73W) 2:25 Effective 2025-08-10 through 2025-08-24
Sun 11:25 Colorado Springs (COS) 14:50 Midway, Chicago (MDW) Southwest Airlines WN 4025 Non-stop Boeing 737-700 (73W) 2:25 Effective 2025-09-07 through 2025-09-28
Non-Direct Flights:
Tue,Wed 05:15 Colorado Springs (COS) 11:15 Midway, Chicago (MDW) Southwest Airlines WN 265 1-stop Boeing 737 MAX 8 (7M8) 5:00 Effective 2025-11-04 through 2025-11-12
Mon-Thu 05:15 Colorado Springs (COS) 11:15 Midway, Chicago (MDW) Southwest Airlines WN 265 1-stop Boeing 737 MAX 8 (7M8) 5:00 Effective 2025-11-17 through 2025-11-20
Mon-Fri 05:15 Colorado Springs (COS) 11:15 Midway, Chicago (MDW) Southwest Airlines WN 265 1-stop Boeing 737 MAX 8 (7M8) 5:00 Effective 2025-12-02 through 2025-12-11
Mon-Wed 05:15 Colorado Springs (COS) 11:15 Midway, Chicago (MDW) Southwest Airlines WN 265 1-stop Boeing 737 MAX 8 (7M8) 5:00 Effective 2025-12-15 through 2025-12-17
Wed,Thu 05:15 Colorado Springs (COS) 11:15 Midway, Chicago (MDW) Southwest Airlines WN 265 1-stop Boeing 737 MAX 8 (7M8) 5:00 Effective 2025-12-24 through 2026-01-01
Sat 14:40 Colorado Springs (COS) 20:20 Midway, Chicago (MDW) Southwest Airlines WN 4230 1-stop Boeing 737-700 (Scimitar Winglets) 4:40 Effective 2025-10-04 through 2025-11-01

A domestic route departing from the Colorado Springs airport (COS) and arriving at Midway, Chicago airport (MDW).
The flight distance is 915 miles, or 1472 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 2:25.

Return (MDW-COS) flights

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All airlines flying from Colorado Springs (COS) to Midway, Chicago (MDW).

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN158

13:30

Colorado Springs (COS)

16:50

Midway, Chicago (MDW)

Operates only on 2025-05-25

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN1823

08:20

Colorado Springs (COS)

11:40

Midway, Chicago (MDW)

Effective 2025-08-09 through 2025-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN1823

09:45

Colorado Springs (COS)

13:10

Midway, Chicago (MDW)

Effective 2025-08-07 through 2025-09-29

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN1823

11:55

Colorado Springs (COS)

15:15

Midway, Chicago (MDW)

Effective 2025-08-05 through 2025-10-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2082

11:10

Colorado Springs (COS)

14:35

Midway, Chicago (MDW)

Effective 2025-11-22 through 2025-11-29

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN2082

11:10

Colorado Springs (COS)

14:35

Midway, Chicago (MDW)

Effective 2025-12-20 through 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN2082

15:10

Colorado Springs (COS)

18:30

Midway, Chicago (MDW)

Effective 2025-11-02 through 2025-11-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Southwest Airlines WN2082

15:10

Colorado Springs (COS)

18:30

Midway, Chicago (MDW)

Effective 2025-11-21 through 2025-11-28

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Southwest Airlines WN2082

15:10

Colorado Springs (COS)

18:30

Midway, Chicago (MDW)

Effective 2025-12-07 through 2025-12-14

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Southwest Airlines WN2082

15:10

Colorado Springs (COS)

18:30

Midway, Chicago (MDW)

Operates only on 2025-12-18

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2082

15:10

Colorado Springs (COS)

18:30

Midway, Chicago (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2082

15:25

Colorado Springs (COS)

18:50

Midway, Chicago (MDW)

Effective 2025-11-25 through 2025-12-01

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2082

15:25

Colorado Springs (COS)

18:50

Midway, Chicago (MDW)

Effective 2025-12-19 through 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Southwest Airlines WN2082

16:30

Colorado Springs (COS)

19:45

Midway, Chicago (MDW)

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN2108

08:25

Colorado Springs (COS)

11:50

Midway, Chicago (MDW)

Effective 2025-10-04 through 2025-11-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN2108

11:45

Colorado Springs (COS)

15:10

Midway, Chicago (MDW)

Effective 2025-10-05 through 2025-10-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2108

13:55

Colorado Springs (COS)

17:15

Midway, Chicago (MDW)

Effective 2025-10-07 through 2025-10-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2108

14:10

Colorado Springs (COS)

17:30

Midway, Chicago (MDW)

Effective 2025-10-02 through 2025-10-31

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN2127

09:55

Colorado Springs (COS)

13:20

Midway, Chicago (MDW)

Effective 2025-06-05 through 2025-07-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2127

09:55

Colorado Springs (COS)

13:20

Midway, Chicago (MDW)

Effective 2025-07-07 through 2025-08-04

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2127

10:05

Colorado Springs (COS)

13:25

Midway, Chicago (MDW)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

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

Southwest Airlines WN2127

12:05

Colorado Springs (COS)

15:30

Midway, Chicago (MDW)

Effective 2025-06-07 through 2025-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN2127

14:55

Colorado Springs (COS)

18:15

Midway, Chicago (MDW)

Effective 2025-06-10 through 2025-07-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2272

13:40

Colorado Springs (COS)

17:00

Midway, Chicago (MDW)

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2340

14:40

Colorado Springs (COS)

18:00

Midway, Chicago (MDW)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2413

16:40

Colorado Springs (COS)

20:00

Midway, Chicago (MDW)

Effective 2025-06-08 through 2025-08-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2681

10:05

Colorado Springs (COS)

13:25

Midway, Chicago (MDW)

Effective 2025-06-10 through 2025-07-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2681

15:50

Colorado Springs (COS)

19:15

Midway, Chicago (MDW)

Effective 2025-06-05 through 2025-07-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2681

15:50

Colorado Springs (COS)

19:15

Midway, Chicago (MDW)

Effective 2025-07-07 through 2025-08-04

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3234

13:50

Colorado Springs (COS)

17:10

Midway, Chicago (MDW)

Valid until 2025-06-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN3234

14:10

Colorado Springs (COS)

17:30

Midway, Chicago (MDW)

Valid until 2025-06-02

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3661

15:55

Colorado Springs (COS)

19:20

Midway, Chicago (MDW)

Valid until 2025-05-18

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3661

15:55

Colorado Springs (COS)

19:20

Midway, Chicago (MDW)

Operates only on 2025-06-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN4025

11:25

Colorado Springs (COS)

14:50

Midway, Chicago (MDW)

Effective 2025-08-10 through 2025-08-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN4025

11:25

Colorado Springs (COS)

14:50

Midway, Chicago (MDW)

Effective 2025-09-07 through 2025-09-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-700 (73W)

Non-Direct Flights:

Southwest Airlines WN265

05:15

Colorado Springs (COS)

11:15

Midway, Chicago (MDW)

Effective 2025-11-04 through 2025-11-12

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 5:00, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN265

05:15

Colorado Springs (COS)

11:15

Midway, Chicago (MDW)

Effective 2025-11-17 through 2025-11-20

Mon

Tue

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 5:00, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN265

05:15

Colorado Springs (COS)

11:15

Midway, Chicago (MDW)

Effective 2025-12-02 through 2025-12-11

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 5:00, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN265

05:15

Colorado Springs (COS)

11:15

Midway, Chicago (MDW)

Effective 2025-12-15 through 2025-12-17

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 5:00, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN265

05:15

Colorado Springs (COS)

11:15

Midway, Chicago (MDW)

Effective 2025-12-24 through 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 5:00, 1-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4230

14:40

Colorado Springs (COS)

20:20

Midway, Chicago (MDW)

Effective 2025-10-04 through 2025-11-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

A domestic route departing from the Colorado Springs airport (COS) and arriving at Midway, Chicago airport (MDW).
The flight distance is 915 miles, or 1472 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 2:25.

Return (MDW-COS) flights

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