How to get to Puerto Rico from Chicago by flight ? You can check flights from Chicago to Puerto Rico below.
You can find flight ticket prices from Chicago to Puerto Rico with our flight tickets search tool below
You take a flight from Chicago Midway to San Juan and cost approximately 480 USD.
You take a bus, shuttle or taxi from San Juan to your destination in Puerto Rico.
Flight | Depart | Arrive | |
---|---|---|---|
WN3469
Southwest Airlines
WN2482
Southwest Airlines
|
05:00
Chicago Midway
10:00
Orlando
|
08:30
Orlando
12:55
San Juan
|
Connect |
WN3448
Southwest Airlines
WN2165 2853
Southwest Airlines
|
05:05
Chicago Midway
10:45
Fort Lauderdale
|
09:05
Fort Lauderdale
13:40
San Juan
|
Connect |
WN3534
Southwest Airlines
WN1412
Southwest Airlines
|
05:05
Chicago Midway
11:50
Orlando
|
08:35
Orlando
14:45
San Juan
|
Connect |
WN3508
Southwest Airlines
WN2165 2853
Southwest Airlines
|
05:10
Chicago Midway
10:45
Fort Lauderdale
|
09:10
Fort Lauderdale
13:40
San Juan
|
Connect |
WN5793
Southwest Airlines
WN5793
Southwest Airlines
|
05:50
Chicago Midway
09:25
Baltimore
|
08:35
Baltimore
13:35
San Juan
|
Connect |
WN3417
Southwest Airlines
WN2026
Southwest Airlines
|
06:00
Chicago Midway
08:50
Nashville
|
07:15
Nashville
14:10
San Juan
|
Connect |
DL2030
Delta
DL1387
Delta
|
06:00
Chicago Midway
11:12
Atlanta
|
08:52
Atlanta
14:57
San Juan
|
Connect |
WN3452
Southwest Airlines
WN3324
Southwest Airlines
|
06:00
Chicago Midway
10:15
Houston Hobby Apt
|
08:35
Houston Hobby Apt
15:40
San Juan
|
Connect |
WN3473
Southwest Airlines
WN4596
Southwest Airlines
|
06:00
Chicago Midway
12:10
Orlando
|
09:30
Orlando
15:05
San Juan
|
Connect |
WN3542
Southwest Airlines
WN1412
Southwest Airlines
|
06:20
Chicago Midway
11:50
Orlando
|
09:50
Orlando
14:45
San Juan
|
Connect |
WN4843
Southwest Airlines
WN3366
Southwest Airlines
|
07:00
Chicago Midway
10:20
Houston Hobby Apt
|
09:30
Houston Hobby Apt
15:45
San Juan
|
Connect |
WN3512
Southwest Airlines
WN4596
Southwest Airlines
|
07:00
Chicago Midway
12:10
Orlando
|
10:35
Orlando
15:05
San Juan
|
Connect |
WN940
Southwest Airlines
WN665
Southwest Airlines
|
07:00
Chicago Midway
11:50
Tampa
|
10:25
Tampa
14:50
San Juan
|
Connect |
WN3512
Southwest Airlines
WN5052 2310
Southwest Airlines
|
07:00
Chicago Midway
14:05
Orlando
|
10:35
Orlando
17:00
San Juan
|
Connect |
WN5702
Southwest Airlines
WN1009
Southwest Airlines
|
07:00
Chicago Midway
12:40
Orlando
|
10:30
Orlando
15:35
San Juan
|
Connect |
DL2701
Delta
DL1387
Delta
|
07:15
Chicago Midway
11:12
Atlanta
|
10:08
Atlanta
14:57
San Juan
|
Connect |
WN3613
Southwest Airlines
WN2863 4073
Southwest Airlines
|
07:20
Chicago Midway
12:05
Baltimore
|
10:15
Baltimore
16:10
San Juan
|
Connect |
WN3146
Southwest Airlines
WN2863 4073
Southwest Airlines
|
07:35
Chicago Midway
12:05
Baltimore
|
10:25
Baltimore
16:10
San Juan
|
Connect |
WN3736
Southwest Airlines
WN3878
Southwest Airlines
|
07:35
Chicago Midway
14:30
Fort Lauderdale
|
11:40
Fort Lauderdale
17:15
San Juan
|
Connect |
WN4057
Southwest Airlines
WN5052 2310
Southwest Airlines
|
07:40
Chicago Midway
14:05
Orlando
|
11:15
Orlando
17:00
San Juan
|
Connect |
WN3881
Southwest Airlines
WN5052 2310
Southwest Airlines
|
08:25
Chicago Midway
14:05
Orlando
|
12:05
Orlando
17:00
San Juan
|
Connect |
WN5972
Southwest Airlines
|
08:50
Chicago Midway
|
14:35 San Juan | Direct |
WN2891 3479
Southwest Airlines
|
09:00
Chicago Midway
|
14:45 San Juan | Direct |
WN3559
Southwest Airlines
WN162 3477
Southwest Airlines
|
09:00
Chicago Midway
15:05
Tampa
|
12:35
Tampa
18:05
San Juan
|
Connect |
WN2269
Southwest Airlines
WN3514 5318
Southwest Airlines
|
10:35
Chicago Midway
16:35
Orlando
|
14:10
Orlando
19:35
San Juan
|
Connect |
WN5843
Southwest Airlines
WN5799
Southwest Airlines
|
10:35
Chicago Midway
16:50
Orlando
|
14:15
Orlando
19:45
San Juan
|
Connect |
WN3841
Southwest Airlines
WN3514 5318
Southwest Airlines
|
11:35
Chicago Midway
16:35
Orlando
|
15:15
Orlando
19:35
San Juan
|
Connect |
WN4105
Southwest Airlines
WN2384 5055
Southwest Airlines
|
12:15
Chicago Midway
18:45
Orlando
|
16:00
Orlando
21:45
San Juan
|
Connect |
WN755
Southwest Airlines
WN6344
Southwest Airlines
|
12:25
Chicago Midway
18:15
Baltimore
|
15:15
Baltimore
22:25
San Juan
|
Connect |
DL2573
Delta
DL549
Delta
|
12:41
Chicago Midway
18:21
Atlanta
|
15:44
Atlanta
22:10
San Juan
|
Connect |
WN1270
Southwest Airlines
WN365
Southwest Airlines
|
13:40
Chicago Midway
20:35
Orlando
|
17:20
Orlando
23:30
San Juan
|
Connect |
WN1270
Southwest Airlines
WN784
Southwest Airlines
|
13:40
Chicago Midway
18:30
Orlando
|
17:20
Orlando
21:30
San Juan
|
Connect |
WN1738
Southwest Airlines
WN2384 5055
Southwest Airlines
|
13:50
Chicago Midway
18:45
Orlando
|
17:30
Orlando
21:45
San Juan
|
Connect |
WN1738
Southwest Airlines
WN4344
Southwest Airlines
|
13:50
Chicago Midway
20:55
Orlando
|
17:30
Orlando
23:50
San Juan
|
Connect |
WN4933
Southwest Airlines
WN5401
Southwest Airlines
|
13:55
Chicago Midway
18:30
Houston Hobby Apt
|
16:35
Houston Hobby Apt
23:55
San Juan
|
Connect |
WN5055
Southwest Airlines
WN2384 5055
Southwest Airlines
|
14:10
Chicago Midway
18:45
Orlando
|
17:55
Orlando
21:45
San Juan
|
Connect |
WN5055
Southwest Airlines
WN3967
Southwest Airlines
|
14:10
Chicago Midway
21:15
Orlando
|
17:55
Orlando
00:10
San Juan
|
Connect |
WN5444
Southwest Airlines
WN262
Southwest Airlines
|
15:15
Chicago Midway
19:50
Tampa
|
18:55
Tampa
22:50
San Juan
|
Connect |
WN3345
Southwest Airlines
WN4344
Southwest Airlines
|
15:45
Chicago Midway
20:55
Orlando
|
19:30
Orlando
23:50
San Juan
|
Connect |
WN5992
Southwest Airlines
WN5992
Southwest Airlines
|
16:15
Chicago Midway
21:05
Fort Lauderdale
|
20:15
Fort Lauderdale
23:45
San Juan
|
Connect |
You take a flight from Chicago O'Hare to San Juan and cost approximately 220 USD.
You take a bus, shuttle or taxi from San Juan to your destination in Puerto Rico.
Flight | Depart | Arrive | |
---|---|---|---|
B6563
JetBlue Airways
B61653
JetBlue Airways
|
05:09
Chicago O'Hare
12:25
Fort Lauderdale
|
09:10
Fort Lauderdale
15:04
San Juan
|
Connect |
B6563
JetBlue Airways
B6353
JetBlue Airways
|
05:09
Chicago O'Hare
11:44
Fort Lauderdale
|
09:10
Fort Lauderdale
14:25
San Juan
|
Connect |
AA1411
American Airlines
AA1613
American Airlines
|
05:36
Chicago O'Hare
12:00
Miami
|
09:40
Miami
14:31
San Juan
|
Connect |
AA1784
American Airlines
AA1852
American Airlines
|
05:45
Chicago O'Hare
09:50
Charlotte
|
08:41
Charlotte
13:23
San Juan
|
Connect |
AA1784
American Airlines
AA783
American Airlines
|
05:45
Chicago O'Hare
11:45
Charlotte
|
08:41
Charlotte
15:13
San Juan
|
Connect |
UA675
United Airlines
UA205
United Airlines
|
06:00
Chicago O'Hare
11:35
Newark
|
09:11
Newark
15:30
San Juan
|
Connect |
DL5947
Delta
DL1063
Delta
|
06:00
Chicago O'Hare
11:58
New York JFK
|
09:17
New York JFK
15:55
San Juan
|
Connect |
UA1754
United Airlines
UA1192
United Airlines
|
06:00
Chicago O'Hare
10:07
Houston
|
08:45
Houston
15:45
San Juan
|
Connect |
AA2498
American Airlines
AA1613
American Airlines
|
06:30
Chicago O'Hare
12:00
Miami
|
10:34
Miami
14:31
San Juan
|
Connect |
DL3153
Delta
DL1387
Delta
|
07:00
Chicago O'Hare
11:12
Atlanta
|
09:55
Atlanta
14:57
San Juan
|
Connect |
AA2507
American Airlines
AA1613
American Airlines
|
07:00
Chicago O'Hare
12:00
Miami
|
11:04
Miami
14:31
San Juan
|
Connect |
DL379
Delta
DL1387
Delta
|
07:00
Chicago O'Hare
11:12
Atlanta
|
09:53
Atlanta
14:57
San Juan
|
Connect |
F9128
Frontier Airlines
|
07:07
Chicago O'Hare
|
13:04 San Juan | Direct |
DL3153
Delta
DL1387
Delta
|
07:10
Chicago O'Hare
11:12
Atlanta
|
10:05
Atlanta
14:57
San Juan
|
Connect |
AA2052
American Airlines
AA783
American Airlines
|
07:24
Chicago O'Hare
11:45
Charlotte
|
10:21
Charlotte
15:13
San Juan
|
Connect |
UA1996
United Airlines
|
07:49
Chicago O'Hare
|
13:37 San Juan | Direct |
UA2182
United Airlines
9K8301
Cape Air
|
08:55
Chicago O'Hare
15:33
Charlotte Amalie
|
14:34
Charlotte Amalie
16:08
San Juan
|
Connect |
B61012
JetBlue Airways
B6261
JetBlue Airways
|
08:58
Chicago O'Hare
15:20
Boston
|
12:24
Boston
19:19
San Juan
|
Connect |
AA395
American Airlines
|
09:05
Chicago O'Hare
|
15:00 San Juan | Direct |
B6906
JetBlue Airways
B62003
JetBlue Airways
|
09:55
Chicago O'Hare
14:50
New York JFK
|
13:10
New York JFK
18:52
San Juan
|
Connect |
B6906
JetBlue Airways
B63
JetBlue Airways
|
09:55
Chicago O'Hare
16:48
New York JFK
|
13:10
New York JFK
20:53
San Juan
|
Connect |
AA1106
American Airlines
AA2481
American Airlines
|
11:45
Chicago O'Hare
16:45
Dallas/Ft.Worth
|
14:08
Dallas/Ft.Worth
22:41
San Juan
|
Connect |
AA2095
American Airlines
AA1529
American Airlines
|
11:50
Chicago O'Hare
17:45
Philadelphia
|
14:50
Philadelphia
21:25
San Juan
|
Connect |
AA335
American Airlines
AA397
American Airlines
|
12:00
Chicago O'Hare
19:40
Miami
|
16:04
Miami
22:15
San Juan
|
Connect |
AA335
American Airlines
AA1570
American Airlines
|
12:00
Chicago O'Hare
17:25
Miami
|
16:04
Miami
20:00
San Juan
|
Connect |
DL5509
Delta
DL433
Delta
|
12:02
Chicago O'Hare
18:20
New York JFK
|
15:35
New York JFK
22:26
San Juan
|
Connect |
DL812
Delta
DL549
Delta
|
12:53
Chicago O'Hare
18:21
Atlanta
|
15:55
Atlanta
22:10
San Juan
|
Connect |
AA2754
American Airlines
AA2481
American Airlines
|
13:20
Chicago O'Hare
16:45
Dallas/Ft.Worth
|
15:45
Dallas/Ft.Worth
22:41
San Juan
|
Connect |
AA1920
American Airlines
AA1529
American Airlines
|
13:35
Chicago O'Hare
17:45
Philadelphia
|
16:40
Philadelphia
21:25
San Juan
|
Connect |
AA2796
American Airlines
AA397
American Airlines
|
13:35
Chicago O'Hare
19:40
Miami
|
17:42
Miami
22:15
San Juan
|
Connect |
DL2062
Delta
DL549
Delta
|
14:00
Chicago O'Hare
18:21
Atlanta
|
17:05
Atlanta
22:10
San Juan
|
Connect |
UA1842
United Airlines
UA1543
United Airlines
|
14:24
Chicago O'Hare
20:13
Newark
|
18:00
Newark
00:15
San Juan
|
Connect |
AA1308
American Airlines
AA2414
American Airlines
|
15:10
Chicago O'Hare
23:00
Miami
|
19:16
Miami
01:33
San Juan
|
Connect |
AA2323
American Airlines
AA2414
American Airlines
|
16:50
Chicago O'Hare
23:00
Miami
|
20:57
Miami
01:33
San Juan
|
Connect |
AA1027
American Airlines
AA2190
American Airlines
|
17:25
Chicago O'Hare
22:50
Dallas/Ft.Worth
|
19:45
Dallas/Ft.Worth
04:22
San Juan
|
Connect |
B62112
JetBlue Airways
B6661
JetBlue Airways
|
17:48
Chicago O'Hare
23:27
Boston
|
21:19
Boston
03:22
San Juan
|
Connect |
AA2300
American Airlines
AA2190
American Airlines
|
18:35
Chicago O'Hare
22:50
Dallas/Ft.Worth
|
21:05
Dallas/Ft.Worth
04:22
San Juan
|
Connect |
F91482
Frontier Airlines
F9123
Frontier Airlines
|
19:13
Chicago O'Hare
01:39
Newark
|
22:29
Newark
06:06
San Juan
|
Connect |
UA695
United Airlines
|
19:35
Chicago O'Hare
|
01:28 San Juan | Direct |
UA1872
United Airlines
UA701
United Airlines
|
19:40
Chicago O'Hare
23:44
Houston
|
22:24
Houston
05:15
San Juan
|
Connect |
You take a flight from Chicago O'Hare to Mayaguez and cost approximately 220 USD.
You take a bus, shuttle or taxi from Mayaguez to your destination in Puerto Rico.
Flight | Depart | Arrive | |
---|---|---|---|
B6563
JetBlue Airways
B61653
JetBlue Airways
9K39
Cape Air
|
05:09
Chicago O'Hare
12:25
Fort Lauderdale
18:48
San Juan
|
09:10
Fort Lauderdale
15:04
San Juan
19:25
Mayaguez
|
Connect |
B6563
JetBlue Airways
B6353
JetBlue Airways
9K39
Cape Air
|
05:09
Chicago O'Hare
11:44
Fort Lauderdale
18:48
San Juan
|
09:10
Fort Lauderdale
14:25
San Juan
19:25
Mayaguez
|
Connect |
AA1784
American Airlines
AA1852
American Airlines
9K37
Cape Air
|
05:45
Chicago O'Hare
09:50
Charlotte
14:50
San Juan
|
08:41
Charlotte
13:23
San Juan
15:27
Mayaguez
|
Connect |
UA1754
United Airlines
UA1192
United Airlines
9K39
Cape Air
|
06:00
Chicago O'Hare
10:07
Houston
18:48
San Juan
|
08:45
Houston
15:45
San Juan
19:25
Mayaguez
|
Connect |
UA675
United Airlines
UA205
United Airlines
9K39
Cape Air
|
06:00
Chicago O'Hare
11:35
Newark
18:48
San Juan
|
09:11
Newark
15:30
San Juan
19:25
Mayaguez
|
Connect |
F9128
Frontier Airlines
9K37
Cape Air
|
07:07
Chicago O'Hare
14:50
San Juan
|
13:04
San Juan
15:27
Mayaguez
|
Connect |
F9128
Frontier Airlines
9K39
Cape Air
|
07:07
Chicago O'Hare
18:48
San Juan
|
13:04
San Juan
19:25
Mayaguez
|
Connect |
UA1996
United Airlines
9K39
Cape Air
|
07:49
Chicago O'Hare
18:48
San Juan
|
13:37
San Juan
19:25
Mayaguez
|
Connect |
UA1996
United Airlines
9K37
Cape Air
|
07:49
Chicago O'Hare
14:50
San Juan
|
13:37
San Juan
15:27
Mayaguez
|
Connect |
UA2182
United Airlines
9K8301
Cape Air
9K39
Cape Air
|
08:55
Chicago O'Hare
15:33
Charlotte Amalie
18:48
San Juan
|
14:34
Charlotte Amalie
16:08
San Juan
19:25
Mayaguez
|
Connect |
AA395
American Airlines
9K39
Cape Air
|
09:05
Chicago O'Hare
18:48
San Juan
|
15:00
San Juan
19:25
Mayaguez
|
Connect |
UA695
United Airlines
9K31
Cape Air
|
19:35
Chicago O'Hare
08:57
San Juan
|
01:28
San Juan
09:34
Mayaguez
|
Connect |
UA1872
United Airlines
UA701
United Airlines
9K31
Cape Air
|
19:40
Chicago O'Hare
23:44
Houston
08:57
San Juan
|
22:24
Houston
05:15
San Juan
09:34
Mayaguez
|
Connect |
You can find hotels and accommodations in Puerto Rico with our hotels search tool below
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