Southwest Airlines flights from Denver (DEN) to Chicago O'Hare (ORD).

FLIGHT SCHEDULE
Direct Flights:
Tue,Wed 10:10 Denver (DEN) 13:55 Chicago O'Hare (ORD) 5 Southwest Airlines WN 104 Non-stop Boeing 737 MAX 8 (7M8) 2:45 Effective 2026-03-10 through 2026-04-01
Sat,Sun 11:25 Denver (DEN) 15:00 Chicago O'Hare (ORD) 5 Southwest Airlines WN 104 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-03-07 through 2026-04-05
Mon,Thu,Fri 11:30 Denver (DEN) 15:05 Chicago O'Hare (ORD) 5 Southwest Airlines WN 104 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-03-05 through 2026-04-06
Sun 10:55 Denver (DEN) 14:25 Chicago O'Hare (ORD) 5 Southwest Airlines WN 1599 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Effective 2026-08-09 through 2026-09-27
Tue,Wed 11:00 Denver (DEN) 14:30 Chicago O'Hare (ORD) 5 Southwest Airlines WN 1599 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-08-04 through 2026-09-30
Mon,Thu,Fri 11:35 Denver (DEN) 15:15 Chicago O'Hare (ORD) 5 Southwest Airlines WN 1599 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2026-08-06 through 2026-09-28
Sat 11:35 Denver (DEN) 15:15 Chicago O'Hare (ORD) 5 Southwest Airlines WN 1599 Non-stop Boeing 737-800 (73H) 2:40 Effective 2026-08-08 through 2026-09-26
Sun 10:50 Denver (DEN) 14:20 Chicago O'Hare (ORD) 5 Southwest Airlines WN 1664 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 11:05 Denver (DEN) 14:35 Chicago O'Hare (ORD) 5 Southwest Airlines WN 1664 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-06-04 through 2026-08-03
Sat 11:25 Denver (DEN) 15:00 Chicago O'Hare (ORD) 5 Southwest Airlines WN 1664 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-06-06 through 2026-08-01
Sat 10:50 Denver (DEN) 14:20 Chicago O'Hare (ORD) 5 Southwest Airlines WN 2367 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-04-11 through 2026-05-30
Mon-Fri,Sun 11:25 Denver (DEN) 15:00 Chicago O'Hare (ORD) 5 Southwest Airlines WN 2367 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-04-07 through 2026-06-03
Sat 10:35 Denver (DEN) 14:05 Chicago O'Hare (ORD) 5 Southwest Airlines WN 2634 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Valid until 2026-01-03
Fri,Sun 10:35 Denver (DEN) 14:05 Chicago O'Hare (ORD) 5 Southwest Airlines WN 2634 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Effective 2026-01-02 through 2026-01-04
Tue,Wed 11:25 Denver (DEN) 15:00 Chicago O'Hare (ORD) 5 Southwest Airlines WN 3725 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-06-09 through 2026-07-29
Sat 10:25 Denver (DEN) 14:05 Chicago O'Hare (ORD) 5 Southwest Airlines WN 4467 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Effective 2026-02-14 through 2026-02-28
Mon,Thu,Fri 10:30 Denver (DEN) 14:05 Chicago O'Hare (ORD) 5 Southwest Airlines WN 4467 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 10:30 Denver (DEN) 14:05 Chicago O'Hare (ORD) 5 Southwest Airlines WN 4467 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-02-20 through 2026-03-01
Non-Direct Flights:
Mon 06:35 Denver (DEN) 13:00 Chicago O'Hare (ORD) 5 Southwest Airlines WN 2271 1-stop Boeing 737 MAX 8 (7M8) 5:25 Operates only on 2026-01-05
Thu,Fri,Sun 12:55 Denver (DEN) 22:35 Chicago O'Hare (ORD) 5 Southwest Airlines WN 4646 2-stop Boeing 737-700 (Scimitar Winglets) 8:40 Effective 2026-01-11 through 2026-01-16
Mon,Sun 12:55 Denver (DEN) 22:35 Chicago O'Hare (ORD) 5 Southwest Airlines WN 4646 2-stop Boeing 737-700 (Scimitar Winglets) 8:40 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 12:55 Denver (DEN) 22:35 Chicago O'Hare (ORD) 5 Southwest Airlines WN 4646 2-stop Boeing 737-700 (Scimitar Winglets) 8:40 Effective 2026-02-01 through 2026-02-06
Mon,Sun 12:55 Denver (DEN) 22:35 Chicago O'Hare (ORD) 5 Southwest Airlines WN 4646 2-stop Boeing 737-700 (Scimitar Winglets) 8:40 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 12:55 Denver (DEN) 22:35 Chicago O'Hare (ORD) 5 Southwest Airlines WN 4646 2-stop Boeing 737-700 (Scimitar Winglets) 8:40 Effective 2026-02-17 through 2026-02-23
Mon 12:55 Denver (DEN) 22:35 Chicago O'Hare (ORD) 5 Southwest Airlines WN 4646 2-stop Boeing 737-700 (Scimitar Winglets) 8:40 Operates only on 2026-03-02

A domestic route departing from the Denver airport (DEN) and arriving at Chicago O'Hare airport (ORD).
The flight distance is 885 miles, or 1425 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 2:30 and 2:45.

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FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN104

10:10

Denver (DEN)

13:55

Chicago O'Hare (ORD) 5

Effective 2026-03-10 through 2026-04-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:45, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN104

11:25

Denver (DEN)

15:00

Chicago O'Hare (ORD) 5

Effective 2026-03-07 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun

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

Direct Flights:

Southwest Airlines WN104

11:30

Denver (DEN)

15:05

Chicago O'Hare (ORD) 5

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1599

10:55

Denver (DEN)

14:25

Chicago O'Hare (ORD) 5

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1599

11:00

Denver (DEN)

14:30

Chicago O'Hare (ORD) 5

Effective 2026-08-04 through 2026-09-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1599

11:35

Denver (DEN)

15:15

Chicago O'Hare (ORD) 5

Effective 2026-08-06 through 2026-09-28

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1599

11:35

Denver (DEN)

15:15

Chicago O'Hare (ORD) 5

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:40, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN1664

10:50

Denver (DEN)

14:20

Chicago O'Hare (ORD) 5

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1664

11:05

Denver (DEN)

14:35

Chicago O'Hare (ORD) 5

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1664

11:25

Denver (DEN)

15:00

Chicago O'Hare (ORD) 5

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2367

10:50

Denver (DEN)

14:20

Chicago O'Hare (ORD) 5

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN2367

11:25

Denver (DEN)

15:00

Chicago O'Hare (ORD) 5

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

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2634

10:35

Denver (DEN)

14:05

Chicago O'Hare (ORD) 5

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 WN2634

10:35

Denver (DEN)

14:05

Chicago O'Hare (ORD) 5

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3725

11:25

Denver (DEN)

15:00

Chicago O'Hare (ORD) 5

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 WN4467

10:25

Denver (DEN)

14:05

Chicago O'Hare (ORD) 5

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4467

10:30

Denver (DEN)

14:05

Chicago O'Hare (ORD) 5

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN4467

10:30

Denver (DEN)

14:05

Chicago O'Hare (ORD) 5

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Non-Direct Flights:

Southwest Airlines WN2271

06:35

Denver (DEN)

13:00

Chicago O'Hare (ORD) 5

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 5:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4646

12:55

Denver (DEN)

22:35

Chicago O'Hare (ORD) 5

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 8:40, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4646

12:55

Denver (DEN)

22:35

Chicago O'Hare (ORD) 5

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 8:40, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4646

12:55

Denver (DEN)

22:35

Chicago O'Hare (ORD) 5

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 8:40, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4646

12:55

Denver (DEN)

22:35

Chicago O'Hare (ORD) 5

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 8:40, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4646

12:55

Denver (DEN)

22:35

Chicago O'Hare (ORD) 5

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

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 8:40, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4646

12:55

Denver (DEN)

22:35

Chicago O'Hare (ORD) 5

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 8:40, 2-stop
Boeing 737-700 (Scimitar Winglets)

A domestic route departing from the Denver airport (DEN) and arriving at Chicago O'Hare airport (ORD).
The flight distance is 885 miles, or 1425 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 2:30 and 2:45.

All DEN-ORD flights

All Southwest Airlines flights

Return (ORD-DEN) flights

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