Airlines with flights from Chicago to San Juan

There are two 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 35 minutes.

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Choose airline

Schedules

Non-stop with Southwest Airlines

  • Total flight time: 4 hours and 35 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 1 flight per week
  • Boeing 737MAX 8 Passenger
MDW
Direct
SJU
 
Flight
Mon
Jan 20
Tue
Jan 21
Wed
Jan 22
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Jan 23
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Jan 24
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Jan 25
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Jan 26
WN3799
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08:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SJU

The timetable & schedule information was updated at 2024-12-13

Via Orlando with Southwest Airlines

  • Total flight time: 6h 00m - 12h 35m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 61 flights per week
  • Boeing 737MAX 8 Passenger
MDW
 
Via MCO
 
SJU
 
Flight
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Jan 20
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WN215
WN2410
05:35
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05:45
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WN1301
WN449
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WN1301
WN2728
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WN1601
WN2128
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05:45
05:45
05:45
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WN2665
WN1409
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WN281
WN2240
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06:35
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WN952
WN2932
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06:55
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WN3210
WN1971
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07:05
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WN3210
WN2728
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08:25
08:25
08:25
08:25
07:05
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WN215
WN1082
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08:00
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WN4325
WN2240
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WN3350
WN1971
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WN3488
WN1971
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09:00
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WN3488
WN209
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WN2420
WN2932
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10:20
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WN1373
WN5615
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10:25
10:25
10:25
10:25
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WN1669
WN5615
10:35
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10:35
WN3378
WN209
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11:25
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WN186
WN209
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11:40
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WN3378
WN1561
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12:25
12:25
12:25
12:25
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WN1158
WN1902
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12:50
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WN4951
WN5615
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13:20
13:20
13:20
13:20
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WN977
WN1902
13:20
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13:20
WN4951
WN1561
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13:20
13:20
13:20
13:20
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WN3254
WN1902
13:25
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13:25
WN2544
WN1561
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13:45
13:45
13:45
13:45
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WN4951
WN1507
14:20
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14:20
WN1035
WN1902
14:20
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14:20
WN1453
WN209
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14:35
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WN154
WN1561
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15:25
15:25
15:25
15:25
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WN1722
WN1507
15:50
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15:50
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SJU

The timetable & schedule information was updated at 2024-12-13

Via Baltimore with Southwest Airlines

  • Total flight time: 6h 35m - 12h 40m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 18 flights per week
  • Boeing 737MAX 8 Passenger
MDW
 
Via BWI
 
SJU
 
Flight
Mon
Jan 20
Tue
Jan 21
Wed
Jan 22
Thu
Jan 23
Fri
Jan 24
Sat
Jan 25
Sun
Jan 26
WN215
WN2410
05:35
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----
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05:35
WN1601
WN2728
05:40
05:45
05:45
05:45
05:45
----
05:40
WN1301
WN449
----
----
----
----
----
05:45
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WN1301
WN2728
----
----
----
----
----
05:45
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WN1601
WN2128
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05:45
05:45
05:45
05:45
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WN2665
WN1409
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05:55
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WN281
WN2240
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06:35
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WN952
WN2932
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06:55
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WN3210
WN1971
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07:05
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WN3210
WN2728
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08:25
08:25
08:25
08:25
07:05
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WN215
WN1082
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08:00
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WN4325
WN2240
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08:35
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WN3350
WN1971
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08:55
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WN3488
WN1971
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09:00
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WN3488
WN209
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09:00
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WN2420
WN2932
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10:20
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WN1373
WN5615
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10:25
10:25
10:25
10:25
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WN1669
WN5615
10:35
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10:35
WN3378
WN209
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11:25
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WN186
WN209
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11:40
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WN3378
WN1561
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12:25
12:25
12:25
12:25
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WN1158
WN1902
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12:50
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WN4951
WN5615
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13:20
13:20
13:20
13:20
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WN977
WN1902
13:20
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13:20
WN4951
WN1561
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13:20
13:20
13:20
13:20
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WN3254
WN1902
13:25
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13:25
WN2544
WN1561
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13:45
13:45
13:45
13:45
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WN4951
WN1507
14:20
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14:20
WN1035
WN1902
14:20
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14:20
WN1453
WN209
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14:35
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WN154
WN1561
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15:25
15:25
15:25
15:25
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WN1722
WN1507
15:50
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15:50
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SJU

The timetable & schedule information was updated at 2024-12-13

Via Atlanta with Delta Air Lines

  • Total flight time: 6h 03m - 9h 29m.
  • Sky Team Alliance
  • 13 flights per week
MDW
 
Via ATL
 
SJU
 
Flight
Mon
Jan 20
Tue
Jan 21
Wed
Jan 22
Thu
Jan 23
Fri
Jan 24
Sat
Jan 25
Sun
Jan 26
DL1285
DL1946
06:00
06:00
06:00
06:00
06:00
06:00
06:00
DL1285
DL1882
06:00
06:00
06:00
06:00
06:00
06:00
06:00
DL1063
DL1791
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10:10
10:10
10:10
10:10
DL2417
DL1861
13:05
13:05
13:05
13:05
13:05
13:05
13:05
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SJU

The timetable & schedule information was updated at 2024-12-13

Via Fort Lauderdale with Southwest Airlines

  • Total flight time: 6h 20m - 12h 35m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 12 flights per week
  • Boeing 737MAX 8 Passenger
MDW
 
Via FLL
 
SJU
 
Flight
Mon
Jan 20
Tue
Jan 21
Wed
Jan 22
Thu
Jan 23
Fri
Jan 24
Sat
Jan 25
Sun
Jan 26
WN215
WN2410
05:35
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----
----
05:35
WN1601
WN2728
05:40
05:45
05:45
05:45
05:45
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05:40
WN1301
WN449
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----
----
----
----
05:45
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WN1301
WN2728
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----
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05:45
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WN1601
WN2128
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05:45
05:45
05:45
05:45
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WN2665
WN1409
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05:55
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WN281
WN2240
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06:35
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WN952
WN2932
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06:55
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WN3210
WN1971
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07:05
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WN3210
WN2728
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08:25
08:25
08:25
08:25
07:05
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WN215
WN1082
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08:00
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WN4325
WN2240
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08:35
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WN3350
WN1971
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08:55
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WN3488
WN1971
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09:00
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WN3488
WN209
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09:00
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WN2420
WN2932
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10:20
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WN1373
WN5615
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10:25
10:25
10:25
10:25
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WN1669
WN5615
10:35
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10:35
WN3378
WN209
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11:25
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WN186
WN209
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11:40
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WN3378
WN1561
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12:25
12:25
12:25
12:25
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WN1158
WN1902
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12:50
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WN4951
WN5615
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13:20
13:20
13:20
13:20
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WN977
WN1902
13:20
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----
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----
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13:20
WN4951
WN1561
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13:20
13:20
13:20
13:20
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WN3254
WN1902
13:25
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----
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13:25
WN2544
WN1561
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13:45
13:45
13:45
13:45
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WN4951
WN1507
14:20
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14:20
WN1035
WN1902
14:20
----
----
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14:20
WN1453
WN209
----
----
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----
----
14:35
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WN154
WN1561
----
15:25
15:25
15:25
15:25
----
----
WN1722
WN1507
15:50
----
----
----
----
----
15:50
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SJU

The timetable & schedule information was updated at 2024-12-13

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