Airlines with flights from Chicago to San Juan
There are three airlines with scheduled flights between MDW and SJU. Southwest is the only airline with non-stop flights from Midway International Airport to Luis Munoz Marin International and the flight time is 4 hours and 40 minutes.
There are three airlines with scheduled flights between MDW and SJU. Southwest is the only airline with non-stop flights from Midway International Airport to Luis Munoz Marin International and the flight time is 4 hours and 40 minutes. Choose airline
Direct
Non-stop
4h 40min
Via Orlando
5h 55min
Via Fort Lauderdale
6h 0min
Via Tampa
6h 15min
Via Atlanta
6h 16min
Via Baltimore
6h 35min
Via Atlanta
7h 7min
Via Orlando
7h 56min
Via Nashville
8h 30min
Via Saint Louis
7h 30min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 4 hours and 40 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
2 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)
MDW
Direct
SJU
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
WN1924
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----
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07:55
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WN2531
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----
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----
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08:45
The timetable & schedule information was updated at 2026-04-21
Via Orlando with Southwest Airlines
-
Total flight time: 5h 55m - 13h 20m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
270 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)
MDW
Via MCO
SJU
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
WN2815
WN1465
WN1465
05:10
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----
05:10
05:10
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----
WN2815
WN1656
WN1656
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05:10
05:10
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----
----
----
WN2815
WN2705
WN2705
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----
----
----
----
----
05:20
WN1428
WN1465
WN1465
----
----
----
----
----
06:10
----
WN2816
WN1465
WN1465
06:30
----
----
06:30
06:30
----
----
WN1267
WN2705
WN2705
----
----
----
----
----
07:40
----
WN4122
WN1656
WN1656
----
----
----
----
----
----
07:45
WN2816
WN4998
WN4998
----
----
----
----
----
07:45
----
WN2816
WN291
WN291
----
----
----
----
----
----
07:50
WN3535
WN396
WN396
----
07:55
07:55
----
----
----
----
WN3222
WN2705
WN2705
----
----
----
----
----
07:55
----
WN1194
WN2705
WN2705
----
----
----
----
----
07:55
----
WN2817
WN1465
WN1465
08:00
----
----
08:00
08:00
----
----
WN1355
WN2705
WN2705
----
----
----
----
----
08:55
----
WN2732
WN396
WN396
----
09:00
09:00
----
----
----
----
WN1102
WN4998
WN4998
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----
----
----
----
----
09:05
WN3222
WN424
WN424
----
09:10
09:10
----
----
----
----
WN2818
WN2705
WN2705
11:00
----
----
11:00
11:00
10:05
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WN1011
WN2705
WN2705
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----
----
----
----
10:15
----
WN3271
WN2705
WN2705
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----
----
----
----
10:20
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WN2327
WN191
WN191
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----
----
----
----
10:25
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WN114
WN2788
WN2788
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----
----
----
----
----
11:15
WN3579
WN2707
WN2707
12:40
----
----
12:40
12:40
----
11:55
WN2818
WN424
WN424
----
12:00
12:00
----
----
----
----
WN2877
WN2707
WN2707
13:20
----
----
13:20
13:20
----
12:00
WN435
WN2707
WN2707
----
----
----
----
----
----
12:00
WN692
WN2708
WN2708
12:50
12:50
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----
WN114
WN191
WN191
----
----
----
----
----
12:50
----
WN644
WN191
WN191
----
----
----
----
----
12:50
----
WN692
WN2707
WN2707
13:30
----
----
13:30
13:30
----
----
WN160
WN250
WN250
----
----
----
----
----
----
13:35
WN2819
WN2706
WN2706
13:40
----
----
13:40
13:40
----
----
WN1779
WN250
WN250
----
----
----
----
----
----
14:50
WN2819
WN2708
WN2708
----
14:50
14:50
----
----
----
----
WN496
WN2708
WN2708
----
15:00
15:00
----
----
----
----
WN2820
WN1656
WN1656
----
----
----
----
----
15:50
----
WN2817
WN2708
WN2708
----
16:35
16:35
----
----
----
----
WN251
WN3644
WN3644
----
----
----
----
----
17:05
----
WN164
WN2708
WN2708
17:10
----
----
17:10
17:10
----
----
The timetable & schedule information was updated at 2026-04-21
Via Fort Lauderdale with Southwest Airlines
-
Total flight time: 6h 00m - 9h 20m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
28 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)
MDW
Via FLL
SJU
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2026-04-21
Via Tampa with Southwest Airlines
-
Total flight time: 6h 15m - 12h 05m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
48 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)
MDW
Via TPA
SJU
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
WN4406
WN4047
WN4047
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----
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12:50
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WN4546
WN4047
WN4047
14:25
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14:25
14:25
12:50
16:05
WN807
WN4047
WN4047
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----
----
----
----
12:55
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WN4546
WN2760
WN2760
----
13:05
13:05
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----
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The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta Air Lines
-
Total flight time: 6h 16m - 10h 34m.
-
Sky Team Alliance
-
96 flights per week
MDW
Via ATL
SJU
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
DL1285
DL1882
DL1882
06:05
06:05
06:05
06:05
06:05
06:05
06:05
DL1063
DL1791
DL1791
11:05
11:05
11:05
11:05
11:05
10:55
11:05
DL2417
DL1791
DL1791
12:41
12:41
12:41
12:41
12:41
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12:41
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Frontier