Airlines with flights from San Juan to Chicago

There are two airlines with scheduled flights between SJU and MDW. Southwest is the only airline with non-stop flights from Luis Munoz Marin International to Midway International Airport and the flight time is 5 hours and 15 minutes.

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Choose airline

Schedules

Non-stop with Southwest Airlines

  • Total flight time: 5 hours and 15 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 1 flight per week
  • Boeing 737MAX 8 Passenger
SJU
Direct
MDW
 
Flight
Mon
Jan 20
Tue
Jan 21
Wed
Jan 22
Thu
Jan 23
Fri
Jan 24
Sat
Jan 25
Sun
Jan 26
WN3331
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14:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR SJU - MDW

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

Via Orlando with Southwest Airlines

  • Total flight time: 6h 30m - 13h 15m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 28 flights per week
  • Boeing 737MAX 8 Passenger
SJU
 
Via MCO
 
MDW
 
Flight
Mon
Jan 20
Tue
Jan 21
Wed
Jan 22
Thu
Jan 23
Fri
Jan 24
Sat
Jan 25
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Jan 26
WN365
WN733
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05:35
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WN365
WN2756
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05:35
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WN365
WN546
05:35
06:50
06:50
06:50
06:50
05:35
05:35
WN365
WN6385
05:35
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WN424
WN5265
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06:00
06:00
06:00
06:00
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WN424
WN4544
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06:05
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WN424
WN2833
06:05
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06:05
WN365
WN4265
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06:50
06:50
06:50
06:50
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WN1109
WN546
07:55
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07:55
WN1109
WN1637
07:55
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07:55
WN1109
WN4265
07:55
09:05
09:05
09:05
09:05
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07:55
WN1109
WN733
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08:45
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WN1109
WN1740
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08:45
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WN1109
WN995
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08:45
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WN1109
WN2756
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08:45
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WN1109
WN4165
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08:45
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WN1109
WN1202
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08:45
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WN1109
WN1786
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08:45
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WN1109
WN647
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09:05
09:05
09:05
09:05
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WN1109
WN1385
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09:05
09:05
09:05
09:05
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WN900
WN493
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11:00
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WN900
WN1325
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11:00
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WN2709
WN995
11:45
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11:45
11:45
WN2709
WN2401
11:45
12:15
12:15
12:15
12:15
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11:45
WN2709
WN2711
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11:45
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WN914
WN1449
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11:45
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WN2709
WN647
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12:15
12:15
12:15
12:15
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WN2709
WN1385
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12:15
12:15
12:15
12:15
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WN2671
WN2037
13:45
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13:45
WN2660
WN2444
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13:55
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WN900
WN427
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14:55
14:55
14:55
14:55
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WN3557
WN2401
15:20
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15:20
WN3557
WN2836
15:20
15:55
15:55
15:55
15:55
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15:20
WN603
WN4710
16:30
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16:30
WN3557
WN2715
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16:40
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SHOW RETURN SCHEDULE
CHECK PRICES FOR SJU - MDW

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

Via Atlanta with Delta Air Lines

  • Total flight time: 6h 26m - 11h 01m.
  • Sky Team Alliance
  • 19 flights per week
SJU
 
Via ATL
 
MDW
 
Flight
Mon
Jan 20
Tue
Jan 21
Wed
Jan 22
Thu
Jan 23
Fri
Jan 24
Sat
Jan 25
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Jan 26
DL1879
DL2417
06:00
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06:00
06:00
06:00
DL1763
DL1739
07:30
07:30
07:30
07:30
07:30
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07:30
DL1840
DL1076
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12:48
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12:48
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DL573
DL1076
13:56
13:56
13:56
13:56
13:56
13:56
13:56
DL1882
DL1076
15:28
15:28
15:28
15:28
15:28
15:28
15:28
SHOW RETURN SCHEDULE
CHECK PRICES FOR SJU - MDW

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

Via Baltimore with Southwest Airlines

  • Total flight time: 7h 00m - 12h 55m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 7 flights per week
  • Boeing 737MAX 8 Passenger
SJU
 
Via BWI
 
MDW
 
Flight
Mon
Jan 20
Tue
Jan 21
Wed
Jan 22
Thu
Jan 23
Fri
Jan 24
Sat
Jan 25
Sun
Jan 26
WN365
WN733
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05:35
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WN365
WN2756
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----
05:35
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WN365
WN546
05:35
06:50
06:50
06:50
06:50
05:35
05:35
WN365
WN6385
05:35
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----
----
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WN424
WN5265
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06:00
06:00
06:00
06:00
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WN424
WN4544
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06:05
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WN424
WN2833
06:05
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06:05
WN365
WN4265
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06:50
06:50
06:50
06:50
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WN1109
WN546
07:55
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07:55
WN1109
WN1637
07:55
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----
07:55
WN1109
WN4265
07:55
09:05
09:05
09:05
09:05
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07:55
WN1109
WN733
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08:45
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WN1109
WN1740
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08:45
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WN1109
WN995
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08:45
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WN1109
WN2756
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08:45
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WN1109
WN4165
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08:45
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WN1109
WN1202
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08:45
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WN1109
WN1786
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08:45
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WN1109
WN647
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09:05
09:05
09:05
09:05
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WN1109
WN1385
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09:05
09:05
09:05
09:05
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WN900
WN493
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11:00
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WN900
WN1325
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11:00
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WN2709
WN995
11:45
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11:45
11:45
WN2709
WN2401
11:45
12:15
12:15
12:15
12:15
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11:45
WN2709
WN2711
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11:45
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WN914
WN1449
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11:45
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WN2709
WN647
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12:15
12:15
12:15
12:15
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WN2709
WN1385
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12:15
12:15
12:15
12:15
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WN2671
WN2037
13:45
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13:45
WN2660
WN2444
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13:55
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WN900
WN427
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14:55
14:55
14:55
14:55
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WN3557
WN2401
15:20
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15:20
WN3557
WN2836
15:20
15:55
15:55
15:55
15:55
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15:20
WN603
WN4710
16:30
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----
----
----
----
16:30
WN3557
WN2715
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----
----
----
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16:40
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SHOW RETURN SCHEDULE
CHECK PRICES FOR SJU - MDW

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

Via Fort Lauderdale with Southwest Airlines

  • Total flight time: 6h 35m - 11h 00m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 5 flights per week
  • Boeing 737MAX 8 Passenger
SJU
 
Via FLL
 
MDW
 
Flight
Mon
Jan 20
Tue
Jan 21
Wed
Jan 22
Thu
Jan 23
Fri
Jan 24
Sat
Jan 25
Sun
Jan 26
WN365
WN733
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----
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----
----
05:35
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WN365
WN2756
----
----
----
----
----
05:35
----
WN365
WN546
05:35
06:50
06:50
06:50
06:50
05:35
05:35
WN365
WN6385
05:35
----
----
----
----
----
----
WN424
WN5265
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06:00
06:00
06:00
06:00
----
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WN424
WN4544
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----
----
----
----
06:05
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WN424
WN2833
06:05
----
----
----
----
----
06:05
WN365
WN4265
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06:50
06:50
06:50
06:50
----
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WN1109
WN546
07:55
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----
----
----
----
07:55
WN1109
WN1637
07:55
----
----
----
----
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07:55
WN1109
WN4265
07:55
09:05
09:05
09:05
09:05
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07:55
WN1109
WN733
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----
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08:45
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WN1109
WN1740
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08:45
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WN1109
WN995
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----
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----
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08:45
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WN1109
WN2756
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08:45
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WN1109
WN4165
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08:45
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WN1109
WN1202
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----
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----
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08:45
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WN1109
WN1786
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----
----
----
----
08:45
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WN1109
WN647
----
09:05
09:05
09:05
09:05
----
----
WN1109
WN1385
----
09:05
09:05
09:05
09:05
----
----
WN900
WN493
----
----
----
----
----
11:00
----
WN900
WN1325
----
----
----
----
----
11:00
----
WN2709
WN995
11:45
----
----
----
----
11:45
11:45
WN2709
WN2401
11:45
12:15
12:15
12:15
12:15
----
11:45
WN2709
WN2711
----
----
----
----
----
11:45
----
WN914
WN1449
----
----
----
----
----
11:45
----
WN2709
WN647
----
12:15
12:15
12:15
12:15
----
----
WN2709
WN1385
----
12:15
12:15
12:15
12:15
----
----
WN2671
WN2037
13:45
----
----
----
----
----
13:45
WN2660
WN2444
----
----
----
----
----
13:55
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WN900
WN427
----
14:55
14:55
14:55
14:55
----
----
WN3557
WN2401
15:20
----
----
----
----
----
15:20
WN3557
WN2836
15:20
15:55
15:55
15:55
15:55
----
15:20
WN603
WN4710
16:30
----
----
----
----
----
16:30
WN3557
WN2715
----
----
----
----
----
16:40
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR SJU - MDW

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

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