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Flight from Puerto Rico to Chicago, IL, USA

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

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

1. San Juan to Chicago O'Hare

  1. You take a bus, shuttle or taxi from your location in Puerto Rico to San Juan.

  2. You take a flight from San Juan to Chicago O'Hare and cost approximately 90 USD.

  3. You take a bus, shuttle or taxi from Chicago O'Hare to your destination in Chicago, IL, USA.

Flight Depart Arrive
UA1803 United Airlines
UA1071 United Airlines
02:01 San Juan
06:30 Newark
05:06 Newark
08:01 Chicago O'Hare
Connect
UA1803 United Airlines
UA2001 United Airlines
02:01 San Juan
07:30 Newark
05:06 Newark
09:01 Chicago O'Hare
Connect
B62504 JetBlue Airways
B61105 JetBlue Airways
03:00 San Juan
08:00 New York JFK
05:56 New York JFK
09:38 Chicago O'Hare
Connect
UA1495 United Airlines
UA1253 United Airlines
03:06 San Juan
07:45 Houston
05:57 Houston
10:20 Chicago O'Hare
Connect
UA2339 United Airlines
UA2483 United Airlines
03:51 San Juan
08:15 Washington Dulles
06:43 Washington Dulles
09:17 Chicago O'Hare
Connect
NK1236 Spirit Airlines
NK478 Spirit Airlines
04:30 San Juan
07:30 Fort Lauderdale-Hollywood International
06:16 Fort Lauderdale-Hollywood International
09:41 Chicago O'Hare
Connect
AA287 American Airlines
AA2796 American Airlines
05:46 San Juan
10:20 Miami
07:39 Miami
12:43 Chicago O'Hare
Connect
AA287 American Airlines
AA1495 American Airlines
05:46 San Juan
08:45 Miami
07:39 Miami
11:20 Chicago O'Hare
Connect
UA598 United Airlines
06:05 San Juan
09:12 Chicago O'Hare Direct
AA1836 American Airlines
AA2758 American Airlines
06:58 San Juan
11:28 Charlotte
10:00 Charlotte
12:45 Chicago O'Hare
Connect
AA1836 American Airlines
AA550 American Airlines
06:58 San Juan
11:05 Charlotte
10:00 Charlotte
12:22 Chicago O'Hare
Connect
DL1858 Delta
DL2204 Delta
07:00 San Juan
11:20 Atlanta
09:55 Atlanta
12:15 Chicago O'Hare
Connect
NK1042 Spirit Airlines
NK2767 Spirit Airlines
07:00 San Juan
11:03 Orlando
09:06 Orlando
12:51 Chicago O'Hare
Connect
NK884 Spirit Airlines
NK2767 Spirit Airlines
07:30 San Juan
11:03 Orlando
09:36 Orlando
12:51 Chicago O'Hare
Connect
AA1091 American Airlines
AA1179 American Airlines
07:55 San Juan
12:25 Miami
09:42 Miami
14:56 Chicago O'Hare
Connect
AA1591 American Airlines
AA1258 American Airlines
08:00 San Juan
12:30 Dallas/Ft.Worth
11:33 Dallas/Ft.Worth
14:54 Chicago O'Hare
Connect
NK2367 Spirit Airlines
NK6 Spirit Airlines
12:21 San Juan
17:26 Fort Lauderdale-Hollywood International
14:08 Fort Lauderdale-Hollywood International
19:37 Chicago O'Hare
Connect
UA434 United Airlines
UA1180 United Airlines
12:55 San Juan
16:59 Newark
16:08 Newark
18:46 Chicago O'Hare
Connect
AA395 American Airlines
14:38 San Juan
18:11 Chicago O'Hare Direct
UA1173 United Airlines
UA550 United Airlines
14:40 San Juan
19:57 Newark
17:51 Newark
21:40 Chicago O'Hare
Connect
AA145 American Airlines
AA1308 American Airlines
14:53 San Juan
19:35 Miami
16:52 Miami
21:56 Chicago O'Hare
Connect
WN4466 Southwest Airlines
WN1597 Southwest Airlines
15:10 San Juan
21:10 Baltimore
18:25 Baltimore
22:20 Chicago O'Hare
Connect
DL1913 Delta
DL5597 Delta
15:20 San Juan
20:50 Detroit
19:14 Detroit
21:23 Chicago O'Hare
Connect
NK539 Spirit Airlines
NK2659 Spirit Airlines
15:30 San Juan
19:39 Tampa
17:37 Tampa
21:21 Chicago O'Hare
Connect
UA2088 United Airlines
15:35 San Juan
18:46 Chicago O'Hare Direct
DL634 Delta
DL1319 Delta
15:38 San Juan
19:59 Atlanta
18:37 Atlanta
20:59 Chicago O'Hare
Connect
AA1496 American Airlines
AA1680 American Airlines
15:38 San Juan
20:35 Philadelphia
18:52 Philadelphia
22:11 Chicago O'Hare
Connect
AA1852 American Airlines
AA2257 American Airlines
15:43 San Juan
20:25 Charlotte
18:41 Charlotte
21:44 Chicago O'Hare
Connect
AA1852 American Airlines
AA873 American Airlines
15:43 San Juan
20:39 Charlotte
18:41 Charlotte
21:56 Chicago O'Hare
Connect
AA90 American Airlines
AA1308 American Airlines
15:53 San Juan
19:35 Miami
17:55 Miami
21:56 Chicago O'Hare
Connect
AC957 Air Canada
AC7683 Air Canada
15:55 San Juan
20:55 Toronto
19:55 Toronto
21:50 Chicago O'Hare
Connect
AA1009 American Airlines
16:36 San Juan
20:10 Chicago O'Hare Direct
AA2773 American Airlines
AA873 American Airlines
16:38 San Juan
20:39 Charlotte
19:35 Charlotte
21:56 Chicago O'Hare
Connect
AA2773 American Airlines
AA2257 American Airlines
16:38 San Juan
20:25 Charlotte
19:35 Charlotte
21:44 Chicago O'Hare
Connect
F9119 Frontier Airlines
F91422 Frontier Airlines
16:45 San Juan
20:39 Miami
18:38 Miami
23:17 Chicago O'Hare
Connect
DL636 Delta
DL1374 Delta
17:05 San Juan
22:36 Atlanta
20:01 Atlanta
23:31 Chicago O'Hare
Connect
UA668 United Airlines
UA1578 United Airlines
17:15 San Juan
21:40 Houston
20:06 Houston
00:10 Chicago O'Hare
Connect
AA1451 American Airlines
AA2323 American Airlines
17:28 San Juan
21:15 Miami
19:27 Miami
23:44 Chicago O'Hare
Connect
NK2354 Spirit Airlines
NK1 Spirit Airlines
19:11 San Juan
21:59 Fort Lauderdale-Hollywood International
20:58 Fort Lauderdale-Hollywood International
00:10 Chicago O'Hare
Connect
F9129 Frontier Airlines
19:39 San Juan
23:20 Chicago O'Hare Direct

2. San Juan to Chicago Midway

  1. You take a bus, shuttle or taxi from your location in Puerto Rico to San Juan.

  2. You take a flight from San Juan to Chicago Midway and cost approximately 470 USD.

  3. You take a bus, shuttle or taxi from Chicago Midway to your destination in Chicago, IL, USA.

Flight Depart Arrive
DL1858 Delta
DL5694 Delta
07:00 San Juan
15:25 Atlanta
09:55 Atlanta
16:23 Chicago Midway
Connect
WN4904 Southwest Airlines
WN4172 Southwest Airlines
07:55 San Juan
14:00 Orlando
10:05 Orlando
15:50 Chicago Midway
Connect
WN4904 Southwest Airlines
WN2443 Southwest Airlines
07:55 San Juan
12:20 Orlando
10:05 Orlando
14:10 Chicago Midway
Connect
WN1473 Southwest Airlines
WN3521 Southwest Airlines
08:00 San Juan
16:05 Orlando
10:10 Orlando
17:50 Chicago Midway
Connect
WN1473 Southwest Airlines
WN1964 Southwest Airlines
08:00 San Juan
11:45 Orlando
10:10 Orlando
13:35 Chicago Midway
Connect
WN1473 Southwest Airlines
WN2551 Southwest Airlines
08:00 San Juan
13:45 Orlando
10:10 Orlando
15:35 Chicago Midway
Connect
WN4003 Southwest Airlines
WN3521 Southwest Airlines
12:25 San Juan
16:05 Orlando
14:35 Orlando
17:50 Chicago Midway
Connect
WN4003 Southwest Airlines
WN4115 Southwest Airlines
12:25 San Juan
17:30 Orlando
14:35 Orlando
19:20 Chicago Midway
Connect
WN4003 Southwest Airlines
WN1645 Southwest Airlines
12:25 San Juan
17:20 Orlando
14:35 Orlando
19:10 Chicago Midway
Connect
WN223 Southwest Airlines
WN568 Southwest Airlines
13:50 San Juan
20:05 Houston Hobby Apt
16:55 Houston Hobby Apt
22:25 Chicago Midway
Connect
WN3852 Southwest Airlines
WN1689 Southwest Airlines
14:35 San Juan
21:40 Tampa
16:50 Tampa
23:20 Chicago Midway
Connect
WN3852 Southwest Airlines
WN1676 Southwest Airlines
14:35 San Juan
17:55 Tampa
16:50 Tampa
19:40 Chicago Midway
Connect
DL634 Delta
DL5662 Delta
15:38 San Juan
20:59 Atlanta
18:37 Atlanta
21:57 Chicago Midway
Connect
WN2602 Southwest Airlines
15:45 San Juan
19:10 Chicago Midway Direct
DL636 Delta
DL5662 Delta
17:05 San Juan
20:59 Atlanta
20:01 Atlanta
21:57 Chicago Midway
Connect
WN3023 Southwest Airlines
WN1689 Southwest Airlines
17:45 San Juan
21:40 Tampa
20:00 Tampa
23:20 Chicago Midway
Connect

3. Mayaguez to Chicago O'Hare

  1. You take a bus, shuttle or taxi from your location in Puerto Rico to Mayaguez.

  2. You take a flight from Mayaguez to Chicago O'Hare and cost approximately 380 USD.

  3. You take a bus, shuttle or taxi from Chicago O'Hare to your destination in Chicago, IL, USA.

Flight Depart Arrive
9K30 Cape Air
UA2088 United Airlines
08:30 Mayaguez
15:35 San Juan
09:07 San Juan
18:46 Chicago O'Hare
Connect
9K30 Cape Air
UA434 United Airlines
UA550 United Airlines
08:30 Mayaguez
12:55 San Juan
19:57 Newark
09:07 San Juan
16:08 Newark
21:40 Chicago O'Hare
Connect
9K30 Cape Air
UA2022 United Airlines
UA487 United Airlines
08:30 Mayaguez
13:56 San Juan
22:07 Washington Dulles
09:07 San Juan
16:50 Washington Dulles
23:12 Chicago O'Hare
Connect
9K30 Cape Air
UA668 United Airlines
UA1578 United Airlines
08:30 Mayaguez
17:15 San Juan
21:40 Houston
09:07 San Juan
20:06 Houston
00:10 Chicago O'Hare
Connect
9K30 Cape Air
9K8151 Cape Air
AA510 American Airlines
08:30 Mayaguez
14:10 San Juan
16:05 Charlotte Amalie
09:07 San Juan
14:45 Charlotte Amalie
19:43 Chicago O'Hare
Connect
9K30 Cape Air
UA1173 United Airlines
UA550 United Airlines
08:30 Mayaguez
14:40 San Juan
19:57 Newark
09:07 San Juan
17:51 Newark
21:40 Chicago O'Hare
Connect
9K30 Cape Air
DL634 Delta
DL1319 Delta
08:30 Mayaguez
15:38 San Juan
19:59 Atlanta
09:07 San Juan
18:37 Atlanta
20:59 Chicago O'Hare
Connect
9K30 Cape Air
3M4142 Silver Airways
UA1707 United Airlines
08:30 Mayaguez
11:15 San Juan
14:24 St Maarten
09:07 San Juan
12:25 St Maarten
18:08 Chicago O'Hare
Connect
9K30 Cape Air
B61052 JetBlue Airways
UA670 United Airlines
08:30 Mayaguez
12:40 San Juan
16:25 Tampa
09:07 San Juan
14:44 Tampa
18:15 Chicago O'Hare
Connect
9K30 Cape Air
B6462 JetBlue Airways
UA503 United Airlines
08:30 Mayaguez
12:16 San Juan
16:30 Boston
09:07 San Juan
15:18 Boston
18:17 Chicago O'Hare
Connect
9K30 Cape Air
B61052 JetBlue Airways
F91446 Frontier Airlines
08:30 Mayaguez
12:40 San Juan
16:25 Tampa
09:07 San Juan
14:44 Tampa
18:19 Chicago O'Hare
Connect
9K30 Cape Air
AA395 American Airlines
08:30 Mayaguez
14:38 San Juan
09:07 San Juan
18:11 Chicago O'Hare
Connect
9K30 Cape Air
NK539 Spirit Airlines
NK2659 Spirit Airlines
08:30 Mayaguez
15:30 San Juan
19:39 Tampa
09:07 San Juan
17:37 Tampa
21:21 Chicago O'Hare
Connect
9K30 Cape Air
UA434 United Airlines
UA1672 United Airlines
08:30 Mayaguez
12:55 San Juan
18:25 Newark
09:07 San Juan
16:08 Newark
20:12 Chicago O'Hare
Connect
9K30 Cape Air
DL1913 Delta
DL5597 Delta
08:30 Mayaguez
15:20 San Juan
20:50 Detroit
09:07 San Juan
19:14 Detroit
21:23 Chicago O'Hare
Connect
9K30 Cape Air
UA434 United Airlines
UA1180 United Airlines
08:30 Mayaguez
12:55 San Juan
16:59 Newark
09:07 San Juan
16:08 Newark
18:46 Chicago O'Hare
Connect
9K30 Cape Air
B61754 JetBlue Airways
UA2386 United Airlines
08:30 Mayaguez
13:35 San Juan
16:26 Fort Lauderdale-Hollywood International
09:07 San Juan
15:14 Fort Lauderdale-Hollywood International
18:40 Chicago O'Hare
Connect
9K30 Cape Air
B61804 JetBlue Airways
B61105 JetBlue Airways
08:30 Mayaguez
10:46 San Juan
17:00 New York JFK
09:07 San Juan
13:44 New York JFK
18:36 Chicago O'Hare
Connect
9K30 Cape Air
AA1852 American Airlines
AA2257 American Airlines
08:30 Mayaguez
15:43 San Juan
20:25 Charlotte
09:07 San Juan
18:41 Charlotte
21:44 Chicago O'Hare
Connect
9K30 Cape Air
9K8031 Cape Air
UA365 United Airlines
08:30 Mayaguez
12:00 San Juan
15:10 Charlotte Amalie
09:07 San Juan
12:35 Charlotte Amalie
18:36 Chicago O'Hare
Connect
9K30 Cape Air
AA2773 American Airlines
AA2257 American Airlines
08:30 Mayaguez
16:38 San Juan
20:25 Charlotte
09:07 San Juan
19:35 Charlotte
21:44 Chicago O'Hare
Connect
9K30 Cape Air
9K8031 Cape Air
AA510 American Airlines
08:30 Mayaguez
12:00 San Juan
16:05 Charlotte Amalie
09:07 San Juan
12:35 Charlotte Amalie
19:43 Chicago O'Hare
Connect

4. Aguadilla to Chicago O'Hare

  1. You take a bus, shuttle or taxi from your location in Puerto Rico to Aguadilla.

  2. You take a flight from Aguadilla to Chicago O'Hare and cost approximately 170 USD.

  3. You take a bus, shuttle or taxi from Chicago O'Hare to your destination in Chicago, IL, USA.

Flight Depart Arrive
UA1162 United Airlines
UA2001 United Airlines
02:25 Aguadilla
07:30 Newark
05:27 Newark
09:01 Chicago O'Hare
Connect
UA1162 United Airlines
UA1660 United Airlines
02:25 Aguadilla
08:30 Newark
05:27 Newark
10:24 Chicago O'Hare
Connect
UA1162 United Airlines
UA1071 United Airlines
02:25 Aguadilla
06:30 Newark
05:27 Newark
08:01 Chicago O'Hare
Connect
NK143 Spirit Airlines
UA1546 United Airlines
04:00 Aguadilla
07:00 Orlando
05:51 Orlando
09:00 Chicago O'Hare
Connect
NK143 Spirit Airlines
NK2767 Spirit Airlines
04:00 Aguadilla
11:03 Orlando
05:51 Orlando
12:51 Chicago O'Hare
Connect
NK374 Spirit Airlines
NK478 Spirit Airlines
04:18 Aguadilla
07:30 Fort Lauderdale-Hollywood International
05:48 Fort Lauderdale-Hollywood International
09:41 Chicago O'Hare
Connect
NK374 Spirit Airlines
NK3040 Spirit Airlines
NK842 Spirit Airlines
04:18 Aguadilla
07:40 Fort Lauderdale-Hollywood International
11:58 Myrtle Beach
05:48 Fort Lauderdale-Hollywood International
09:21 Myrtle Beach
13:08 Chicago O'Hare
Connect
NK374 Spirit Airlines
NK198 Spirit Airlines
NK2767 Spirit Airlines
04:18 Aguadilla
07:49 Fort Lauderdale-Hollywood International
11:03 Orlando
05:48 Fort Lauderdale-Hollywood International
08:46 Orlando
12:51 Chicago O'Hare
Connect
B6838 JetBlue Airways
B6105 JetBlue Airways
05:01 Aguadilla
12:00 New York JFK
08:01 New York JFK
13:37 Chicago O'Hare
Connect
B6730 JetBlue Airways
UA1500 United Airlines
11:40 Aguadilla
14:35 Orlando
13:37 Orlando
16:35 Chicago O'Hare
Connect
B6730 JetBlue Airways
AA2671 American Airlines
11:40 Aguadilla
14:51 Orlando
13:37 Orlando
17:06 Chicago O'Hare
Connect
B6730 JetBlue Airways
AA337 American Airlines
11:40 Aguadilla
16:00 Orlando
13:37 Orlando
18:15 Chicago O'Hare
Connect
B61092 JetBlue Airways
AA1274 American Airlines
15:09 Aguadilla
18:30 Fort Lauderdale-Hollywood International
16:49 Fort Lauderdale-Hollywood International
21:03 Chicago O'Hare
Connect

References

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