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Flight from Chicago to Puerto Rico

How to get to Puerto Rico from Chicago by flight ? You can check flights from Chicago to Puerto Rico below.

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You can find flight ticket prices from Chicago to Puerto Rico with our flight tickets search tool below

1. Chicago Midway to San Juan

  1. You take a flight from Chicago Midway to San Juan and cost approximately 480 USD.

  2. 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

2. Chicago O'Hare to San Juan

  1. You take a flight from Chicago O'Hare to San Juan and cost approximately 220 USD.

  2. 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

3. Chicago O'Hare to Mayaguez

  1. You take a flight from Chicago O'Hare to Mayaguez and cost approximately 220 USD.

  2. 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

References

Find Hotels in Puerto Rico

You can find hotels and accommodations in Puerto Rico with our hotels search tool below

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