All airlines flying from Luis Munoz Marin, San Juan (SJU) to Chicago Midway (MDW).

FLIGHT SCHEDULE
Direct Flights:
Sat 16:20 Luis Munoz Marin, San Juan (SJU) B 19:40 Chicago Midway (MDW) Southwest Airlines WN 342 Non-stop Boeing 737 MAX 8 (7M8) 5:20 Effective 2026-02-14 through 2026-02-28
Sat 14:35 Luis Munoz Marin, San Juan (SJU) B 18:55 Chicago Midway (MDW) Southwest Airlines WN 512 Non-stop Boeing 737-800 (73H) 5:20 Effective 2026-03-14 through 2026-04-04
Sat 15:35 Luis Munoz Marin, San Juan (SJU) B 18:55 Chicago Midway (MDW) Southwest Airlines WN 512 Non-stop Boeing 737-800 (73H) 5:20 Operates only on 2026-03-07
Sat 15:50 Luis Munoz Marin, San Juan (SJU) B 19:10 Chicago Midway (MDW) Southwest Airlines WN 910 Non-stop Boeing 737 MAX 8 (7M8) 5:20 Valid until 2026-01-03
Sat 13:10 Luis Munoz Marin, San Juan (SJU) B 17:20 Chicago Midway (MDW) Southwest Airlines WN 1093 Non-stop Boeing 737 MAX 8 (7M8) 5:10 Effective 2026-04-11 through 2026-05-30
Sat 05:30 Luis Munoz Marin, San Juan (SJU) B 09:20 Chicago Midway (MDW) Southwest Airlines WN 2177 Non-stop Boeing 737 MAX 8 (7M8) 4:50 Effective 2026-06-06 through 2026-08-01
Sun 14:20 Luis Munoz Marin, San Juan (SJU) B 18:40 Chicago Midway (MDW) Southwest Airlines WN 2536 Non-stop Boeing 737-700 (Scimitar Winglets) 5:20 Effective 2026-03-08 through 2026-04-05
Sat 15:00 Luis Munoz Marin, San Juan (SJU) B 18:20 Chicago Midway (MDW) Southwest Airlines WN 2952 Non-stop Boeing 737-700 (Scimitar Winglets) 5:20 Effective 2026-01-10 through 2026-02-07
Sun 16:30 Luis Munoz Marin, San Juan (SJU) B 20:20 Chicago Midway (MDW) Southwest Airlines WN 3639 Non-stop Boeing 737-800 (73H) 4:50 Effective 2026-06-07 through 2026-08-02

An international route departing from Luis Munoz Marin, San Juan airport, Puerto Rico (SJU) and arriving at Chicago Midway airport, United States (MDW).
The flight distance is 2058 miles, or 3311 km.
The timezone of the departure airport is UTC-4 , 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 4:50 and 5:20.

Return (MDW-SJU) flights

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All airlines flying from Luis Munoz Marin, San Juan (SJU) to Chicago Midway (MDW).

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN342

16:20

Luis Munoz Marin, San Juan (SJU) B

19:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN512

14:35

Luis Munoz Marin, San Juan (SJU) B

18:55

Chicago Midway (MDW)

Effective 2026-03-14 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN512

15:35

Luis Munoz Marin, San Juan (SJU) B

18:55

Chicago Midway (MDW)

Operates only on 2026-03-07

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN910

15:50

Luis Munoz Marin, San Juan (SJU) B

19:10

Chicago Midway (MDW)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1093

13:10

Luis Munoz Marin, San Juan (SJU) B

17:20

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2177

05:30

Luis Munoz Marin, San Juan (SJU) B

09:20

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:50, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2536

14:20

Luis Munoz Marin, San Juan (SJU) B

18:40

Chicago Midway (MDW)

Effective 2026-03-08 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 5:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2952

15:00

Luis Munoz Marin, San Juan (SJU) B

18:20

Chicago Midway (MDW)

Effective 2026-01-10 through 2026-02-07

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3639

16:30

Luis Munoz Marin, San Juan (SJU) B

20:20

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:50, non-stop
Boeing 737-800 (73H)

An international route departing from Luis Munoz Marin, San Juan airport, Puerto Rico (SJU) and arriving at Chicago Midway airport, United States (MDW).
The flight distance is 2058 miles, or 3311 km.
The timezone of the departure airport is UTC-4 , 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 4:50 and 5:20.

Return (MDW-SJU) flights

Feedback - Disclaimer - Privacy