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Flight from Puerto Rico to Chicago (Station), IL, USA

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

Search Transfer from Puerto Rico to Chicago (Station), IL, USA

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

1. 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 270 USD.

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

Flight Depart Arrive
F9105 Frontier Airlines
F91022 Frontier Airlines
03:00 San Juan
08:33 Orlando
06:05 Orlando
10:35 Chicago Midway
Connect
WN2546 Southwest Airlines
WN137 Southwest Airlines
05:00 San Juan
12:30 Baltimore
09:05 Baltimore
13:30 Chicago Midway
Connect
WN4550 Southwest Airlines
WN3189 Southwest Airlines
05:00 San Juan
09:55 Orlando
08:00 Orlando
11:35 Chicago Midway
Connect
WN3024 Southwest Airlines
WN3815 Southwest Airlines
05:30 San Juan
11:05 Baltimore
09:35 Baltimore
12:00 Chicago Midway
Connect
WN121 Southwest Airlines
WN766 Southwest Airlines
05:30 San Juan
11:00 Orlando
08:35 Orlando
12:40 Chicago Midway
Connect
WN121 Southwest Airlines
WN544 Southwest Airlines
05:30 San Juan
09:30 Orlando
08:35 Orlando
11:10 Chicago Midway
Connect
WN3111 4208 Southwest Airlines
WN854 Southwest Airlines
06:00 San Juan
10:15 Fort Lauderdale-Hollywood International
08:45 Fort Lauderdale-Hollywood International
12:20 Chicago Midway
Connect
WN3111 4208 Southwest Airlines
WN4557 Southwest Airlines
06:00 San Juan
13:45 Fort Lauderdale-Hollywood International
08:45 Fort Lauderdale-Hollywood International
15:55 Chicago Midway
Connect
WN3 Southwest Airlines
WN1717 Southwest Airlines
06:45 San Juan
14:00 Orlando
09:50 Orlando
15:45 Chicago Midway
Connect
DL1763 Delta
DL2526 Delta
07:00 San Juan
15:35 Atlanta
10:41 Atlanta
16:27 Chicago Midway
Connect
WN5717 Southwest Airlines
WN3141 Southwest Airlines
WN1120 Southwest Airlines
09:55 San Juan
13:55 Orlando
16:15 Birmingham
12:55 Orlando
14:35 Birmingham
18:00 Chicago Midway
Connect
WN5717 Southwest Airlines
WN1651 Southwest Airlines
09:55 San Juan
14:25 Orlando
12:55 Orlando
16:10 Chicago Midway
Connect
WN1717 Southwest Airlines
WN1717 Southwest Airlines
10:05 San Juan
14:00 Orlando
13:05 Orlando
15:45 Chicago Midway
Connect
WN1717 Southwest Airlines
WN3345 Southwest Airlines
10:05 San Juan
17:40 Orlando
13:05 Orlando
19:35 Chicago Midway
Connect
WN1717 Southwest Airlines
WN2240 Southwest Airlines
10:05 San Juan
15:10 Orlando
13:05 Orlando
16:55 Chicago Midway
Connect
WN4783 Southwest Airlines
WN2494 Southwest Airlines
11:45 San Juan
19:00 Baltimore
15:55 Baltimore
19:55 Chicago Midway
Connect
WN1335 Southwest Airlines
WN4780 Southwest Airlines
12:05 San Juan
18:55 Orlando
15:05 Orlando
20:45 Chicago Midway
Connect
WN4008 Southwest Airlines
WN3345 Southwest Airlines
13:00 San Juan
17:40 Orlando
16:05 Orlando
19:35 Chicago Midway
Connect
WN4008 Southwest Airlines
WN4295 Southwest Airlines
13:00 San Juan
19:45 Orlando
16:05 Orlando
21:30 Chicago Midway
Connect
WN4008 Southwest Airlines
WN4780 Southwest Airlines
13:00 San Juan
18:55 Orlando
16:05 Orlando
20:45 Chicago Midway
Connect
WN1205 Southwest Airlines
WN3258 Southwest Airlines
13:20 San Juan
20:00 Tampa
16:25 Tampa
21:35 Chicago Midway
Connect
WN2772 Southwest Airlines
WN2183 Southwest Airlines
13:35 San Juan
19:45 Fort Lauderdale-Hollywood International
16:25 Fort Lauderdale-Hollywood International
21:55 Chicago Midway
Connect
WN3181 Southwest Airlines
WN4780 Southwest Airlines
14:20 San Juan
18:55 Orlando
17:25 Orlando
20:45 Chicago Midway
Connect
WN3181 Southwest Airlines
WN4295 Southwest Airlines
14:20 San Juan
19:45 Orlando
17:25 Orlando
21:30 Chicago Midway
Connect
WN3303 Southwest Airlines
WN3756 Southwest Airlines
14:40 San Juan
21:45 Nashville
17:55 Nashville
23:15 Chicago Midway
Connect
DL634 Delta
DL2819 Delta
14:47 San Juan
21:59 Atlanta
18:32 Atlanta
22:48 Chicago Midway
Connect
WN946 Southwest Airlines
15:25 San Juan
19:25 Chicago Midway Direct
WN4771 Southwest Airlines
WN5571 Southwest Airlines
16:00 San Juan
21:55 Baltimore
20:10 Baltimore
22:55 Chicago Midway
Connect
WN419 Southwest Airlines
WN174 Southwest Airlines
16:05 San Juan
22:55 Orlando
19:05 Orlando
00:35 Chicago Midway
Connect
WN419 Southwest Airlines
WN428 Southwest Airlines
16:05 San Juan
21:50 Orlando
19:05 Orlando
23:30 Chicago Midway
Connect
WN4188 Southwest Airlines
WN4213 Southwest Airlines
17:15 San Juan
22:15 Houston Hobby Apt
20:50 Houston Hobby Apt
00:35 Chicago Midway
Connect
WN840 Southwest Airlines
WN1732 Southwest Airlines
17:45 San Juan
22:50 Orlando
20:45 Orlando
00:30 Chicago Midway
Connect
WN1719 Southwest Airlines
WN428 Southwest Airlines
17:55 San Juan
21:50 Orlando
21:00 Orlando
23:30 Chicago Midway
Connect
WN1719 Southwest Airlines
WN174 Southwest Airlines
17:55 San Juan
22:55 Orlando
21:00 Orlando
00:35 Chicago Midway
Connect

2. 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 220 USD.

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

Flight Depart Arrive
UA2218 United Airlines
UA1071 United Airlines
01:05 San Juan
06:29 Newark
05:06 Newark
07:59 Chicago O'Hare
Connect
UA2218 United Airlines
UA1793 United Airlines
01:05 San Juan
07:59 Newark
05:06 Newark
09:27 Chicago O'Hare
Connect
B61904 JetBlue Airways
B61105 JetBlue Airways
02:59 San Juan
08:07 New York JFK
06:51 New York JFK
09:55 Chicago O'Hare
Connect
F9105 Frontier Airlines
F944 Frontier Airlines
03:00 San Juan
07:30 Orlando
06:05 Orlando
09:34 Chicago O'Hare
Connect
WN2546 Southwest Airlines
WN1956 Southwest Airlines
05:00 San Juan
11:40 Baltimore
09:05 Baltimore
12:45 Chicago O'Hare
Connect
WN4550 Southwest Airlines
WN2596 Southwest Airlines
05:00 San Juan
09:50 Orlando
08:00 Orlando
11:50 Chicago O'Hare
Connect
WN3024 Southwest Airlines
WN1956 Southwest Airlines
05:30 San Juan
11:40 Baltimore
09:35 Baltimore
12:45 Chicago O'Hare
Connect
WN121 Southwest Airlines
WN2678 Southwest Airlines
05:30 San Juan
09:55 Orlando
08:35 Orlando
11:55 Chicago O'Hare
Connect
AA1528 American Airlines
AA1920 American Airlines
05:35 San Juan
10:46 Philadelphia
09:32 Philadelphia
12:11 Chicago O'Hare
Connect
AA1528 American Airlines
AA1071 American Airlines
05:35 San Juan
12:39 Philadelphia
09:32 Philadelphia
13:57 Chicago O'Hare
Connect
WN3111 4208 Southwest Airlines
WN3119 Southwest Airlines
06:00 San Juan
11:55 Fort Lauderdale-Hollywood International
08:45 Fort Lauderdale-Hollywood International
14:15 Chicago O'Hare
Connect
AA1913 American Airlines
06:00 San Juan
10:09 Chicago O'Hare Direct
WN2555 Southwest Airlines
WN830 Southwest Airlines
06:30 San Juan
11:10 Tampa
09:35 Tampa
13:00 Chicago O'Hare
Connect
AA1236 American Airlines
AA791 American Airlines
06:33 San Juan
10:10 Miami
09:15 Miami
12:33 Chicago O'Hare
Connect
DL1763 Delta
DL739 Delta
07:00 San Juan
13:15 Atlanta
10:41 Atlanta
14:19 Chicago O'Hare
Connect
UA2048 United Airlines
UA2338 United Airlines
07:30 San Juan
12:55 Washington Dulles
11:23 Washington Dulles
13:55 Chicago O'Hare
Connect
AA386 American Airlines
AA2279 American Airlines
07:57 San Juan
13:49 Miami
10:46 Miami
16:17 Chicago O'Hare
Connect
AA783 American Airlines
AA2895 American Airlines
08:09 San Juan
13:10 Charlotte
11:55 Charlotte
14:15 Chicago O'Hare
Connect
AA783 American Airlines
AA424 American Airlines
08:09 San Juan
15:12 Charlotte
11:55 Charlotte
16:17 Chicago O'Hare
Connect
NK3147 Spirit Airlines
NK3164 Spirit Airlines
09:15 San Juan
13:30 Miami
12:13 Miami
16:02 Chicago O'Hare
Connect
WN1717 Southwest Airlines
WN3327 Southwest Airlines
10:05 San Juan
14:10 Orlando
13:05 Orlando
16:15 Chicago O'Hare
Connect
NK884 Spirit Airlines
NK912 Spirit Airlines
10:17 San Juan
16:24 Orlando
13:26 Orlando
18:36 Chicago O'Hare
Connect
UA2022 United Airlines
UA2608 United Airlines
11:10 San Juan
17:22 Washington Dulles
15:07 Washington Dulles
18:38 Chicago O'Hare
Connect
NK893 Spirit Airlines
NK912 Spirit Airlines
11:40 San Juan
16:24 Orlando
14:49 Orlando
18:36 Chicago O'Hare
Connect
NK319 Spirit Airlines
NK912 Spirit Airlines
11:56 San Juan
16:24 Orlando
15:05 Orlando
18:36 Chicago O'Hare
Connect
AA1847 American Airlines
AA2857 American Airlines
12:03 San Juan
18:11 Charlotte
15:44 Charlotte
19:25 Chicago O'Hare
Connect
AA1341 American Airlines
AA1159 American Airlines
12:05 San Juan
16:24 Miami
14:50 Miami
18:48 Chicago O'Hare
Connect
DL639 Delta
DL5784 Delta
13:15 San Juan
19:35 New York JFK
17:14 New York JFK
21:37 Chicago O'Hare
Connect
UA1495 United Airlines
UA2425 United Airlines
13:23 San Juan
18:09 Houston
17:16 Houston
20:55 Chicago O'Hare
Connect
UA1173 United Airlines
UA1234 United Airlines
13:38 San Juan
19:55 Newark
17:55 Newark
21:30 Chicago O'Hare
Connect
AA1613 American Airlines
AA2457 American Airlines
13:51 San Juan
19:36 Miami
16:39 Miami
22:01 Chicago O'Hare
Connect
AC1719 Air Canada
AC8915 Air Canada
14:05 San Juan
20:30 Toronto
19:10 Toronto
21:20 Chicago O'Hare
Connect
UA2088 United Airlines
14:20 San Juan
18:33 Chicago O'Hare Direct
DL634 Delta
DL1453 Delta
14:47 San Juan
19:59 Atlanta
18:32 Atlanta
21:08 Chicago O'Hare
Connect
AA1184 American Airlines
15:18 San Juan
19:34 Chicago O'Hare Direct
AA1591 American Airlines
AA2346 American Airlines
15:26 San Juan
20:40 Dallas/Ft.Worth
19:30 Dallas/Ft.Worth
23:05 Chicago O'Hare
Connect
AA1852 American Airlines
AA689 American Airlines
15:35 San Juan
22:37 Charlotte
19:21 Charlotte
23:39 Chicago O'Hare
Connect
AA1852 American Airlines
AA815 American Airlines
15:35 San Juan
20:12 Charlotte
19:21 Charlotte
21:15 Chicago O'Hare
Connect
AA1790 American Airlines
AA2323 American Airlines
16:04 San Juan
21:13 Miami
18:54 Miami
23:43 Chicago O'Hare
Connect
UA668 United Airlines
UA2420 United Airlines
16:30 San Juan
22:07 Houston
20:23 Houston
00:45 Chicago O'Hare
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 650 USD.

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

Flight Depart Arrive
9K34 Cape Air
AA1341 American Airlines
AA1159 American Airlines
08:20 Mayaguez
12:05 San Juan
16:24 Miami
08:57 San Juan
14:50 Miami
18:48 Chicago O'Hare
Connect
9K34 Cape Air
UA2022 United Airlines
UA2608 United Airlines
08:20 Mayaguez
11:10 San Juan
17:22 Washington Dulles
08:57 San Juan
15:07 Washington Dulles
18:38 Chicago O'Hare
Connect
9K34 Cape Air
B61454 JetBlue Airways
B6566 JetBlue Airways
08:20 Mayaguez
10:35 San Juan
21:45 Fort Lauderdale-Hollywood International
08:57 San Juan
13:17 Fort Lauderdale-Hollywood International
23:56 Chicago O'Hare
Connect
9K34 Cape Air
B6808 JetBlue Airways
AA4010 American Airlines
08:20 Mayaguez
13:12 San Juan
18:35 Boston
08:57 San Juan
17:20 Boston
20:30 Chicago O'Hare
Connect
9K34 Cape Air
B61604 JetBlue Airways
AA532 American Airlines
08:20 Mayaguez
10:09 San Juan
15:55 New York JFK
08:57 San Juan
14:06 New York JFK
17:34 Chicago O'Hare
Connect
9K34 Cape Air
9K8051 Cape Air
UA365 United Airlines
08:20 Mayaguez
09:50 San Juan
14:10 Charlotte Amalie
08:57 San Juan
10:25 Charlotte Amalie
18:34 Chicago O'Hare
Connect
9K34 Cape Air
UA1495 United Airlines
UA715 United Airlines
08:20 Mayaguez
13:23 San Juan
20:09 Houston
08:57 San Juan
17:16 Houston
22:52 Chicago O'Hare
Connect
9K34 Cape Air
UA1495 United Airlines
UA2425 United Airlines
08:20 Mayaguez
13:23 San Juan
18:09 Houston
08:57 San Juan
17:16 Houston
20:55 Chicago O'Hare
Connect
9K34 Cape Air
UA1173 United Airlines
UA1234 United Airlines
08:20 Mayaguez
13:38 San Juan
19:55 Newark
08:57 San Juan
17:55 Newark
21:30 Chicago O'Hare
Connect
9K34 Cape Air
UA2088 United Airlines
08:20 Mayaguez
14:20 San Juan
08:57 San Juan
18:33 Chicago O'Hare
Connect
9K34 Cape Air
AA1847 American Airlines
AA2857 American Airlines
08:20 Mayaguez
12:03 San Juan
18:11 Charlotte
08:57 San Juan
15:44 Charlotte
19:25 Chicago O'Hare
Connect
9K34 Cape Air
UA2022 United Airlines
UA2467 United Airlines
08:20 Mayaguez
11:10 San Juan
22:19 Washington Dulles
08:57 San Juan
15:07 Washington Dulles
23:25 Chicago O'Hare
Connect
9K34 Cape Air
AA1184 American Airlines
08:20 Mayaguez
15:18 San Juan
08:57 San Juan
19:34 Chicago O'Hare
Connect
9K38 Cape Air
UA668 United Airlines
UA2420 United Airlines
10:19 Mayaguez
16:30 San Juan
22:07 Houston
10:56 San Juan
20:23 Houston
00:45 Chicago O'Hare
Connect
9K38 Cape Air
B6808 JetBlue Airways
AA4010 American Airlines
10:19 Mayaguez
13:12 San Juan
18:35 Boston
10:56 San Juan
17:20 Boston
20:30 Chicago O'Hare
Connect
9K38 Cape Air
UA1495 United Airlines
UA715 United Airlines
10:19 Mayaguez
13:23 San Juan
20:09 Houston
10:56 San Juan
17:16 Houston
22:52 Chicago O'Hare
Connect
9K38 Cape Air
AC1719 Air Canada
AC8915 Air Canada
10:19 Mayaguez
14:05 San Juan
20:30 Toronto
10:56 San Juan
19:10 Toronto
21:20 Chicago O'Hare
Connect
9K38 Cape Air
AA1184 American Airlines
10:19 Mayaguez
15:18 San Juan
10:56 San Juan
19:34 Chicago O'Hare
Connect
9K38 Cape Air
UA1495 United Airlines
UA2420 United Airlines
10:19 Mayaguez
13:23 San Juan
22:07 Houston
10:56 San Juan
17:16 Houston
00:45 Chicago O'Hare
Connect
9K38 Cape Air
UA1173 United Airlines
UA1234 United Airlines
10:19 Mayaguez
13:38 San Juan
19:55 Newark
10:56 San Juan
17:55 Newark
21:30 Chicago O'Hare
Connect
9K38 Cape Air
AA1852 American Airlines
AA815 American Airlines
10:19 Mayaguez
15:35 San Juan
20:12 Charlotte
10:56 San Juan
19:21 Charlotte
21:15 Chicago O'Hare
Connect
9K38 Cape Air
UA1495 United Airlines
UA2425 United Airlines
10:19 Mayaguez
13:23 San Juan
18:09 Houston
10:56 San Juan
17:16 Houston
20:55 Chicago O'Hare
Connect
9K38 Cape Air
DL634 Delta
DL1453 Delta
10:19 Mayaguez
14:47 San Juan
19:59 Atlanta
10:56 San Juan
18:32 Atlanta
21:08 Chicago O'Hare
Connect
9K38 Cape Air
UA2088 United Airlines
10:19 Mayaguez
14:20 San Juan
10:56 San Juan
18:33 Chicago O'Hare
Connect
9K38 Cape Air
AA1847 American Airlines
AA2857 American Airlines
10:19 Mayaguez
12:03 San Juan
18:11 Charlotte
10:56 San Juan
15:44 Charlotte
19:25 Chicago O'Hare
Connect
9K38 Cape Air
AA1341 American Airlines
AA1159 American Airlines
10:19 Mayaguez
12:05 San Juan
16:24 Miami
10:56 San Juan
14:50 Miami
18:48 Chicago O'Hare
Connect
9K40 Cape Air
AA1790 American Airlines
AA2323 American Airlines
14:32 Mayaguez
16:04 San Juan
21:13 Miami
15:09 San Juan
18:54 Miami
23:43 Chicago O'Hare
Connect
9K40 Cape Air
UA668 United Airlines
UA2420 United Airlines
14:32 Mayaguez
16:30 San Juan
22:07 Houston
15:09 San Juan
20:23 Houston
00:45 Chicago O'Hare
Connect
9K41 Cape Air
B61904 JetBlue Airways
B61105 JetBlue Airways
17:16 Mayaguez
02:59 San Juan
08:07 New York JFK
17:53 San Juan
06:51 New York JFK
09:55 Chicago O'Hare
Connect
9K41 Cape Air
UA2218 United Airlines
UA1793 United Airlines
17:16 Mayaguez
01:05 San Juan
07:59 Newark
17:53 San Juan
05:06 Newark
09:27 Chicago O'Hare
Connect
9K41 Cape Air
UA2218 United Airlines
UA1071 United Airlines
17:16 Mayaguez
01:05 San Juan
06:29 Newark
17:53 San Juan
05:06 Newark
07:59 Chicago O'Hare
Connect
9K41 Cape Air
B6562 JetBlue Airways
AA2265 American Airlines
17:16 Mayaguez
18:50 San Juan
05:30 Boston
17:53 San Juan
22:50 Boston
07:22 Chicago O'Hare
Connect

4. Ponce to Chicago O'Hare

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

  2. You take a flight from Ponce to Chicago O'Hare and cost approximately 270 USD.

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

Flight Depart Arrive
B6746 JetBlue Airways
B6105 JetBlue Airways
05:31 Ponce
13:21 New York JFK
09:29 New York JFK
15:12 Chicago O'Hare
Connect
B6746 JetBlue Airways
AA532 American Airlines
05:31 Ponce
15:55 New York JFK
09:29 New York JFK
17:34 Chicago O'Hare
Connect
NK3027 Spirit Airlines
NK621 Spirit Airlines
NK992 Spirit Airlines
13:30 Ponce
17:55 Orlando
20:59 New Orleans
16:35 Orlando
18:50 New Orleans
23:34 Chicago O'Hare
Connect
NK3027 Spirit Airlines
UA1626 United Airlines
13:30 Ponce
17:35 Orlando
16:35 Orlando
19:40 Chicago O'Hare
Connect
NK3027 Spirit Airlines
AA1638 American Airlines
AA815 American Airlines
13:30 Ponce
17:27 Orlando
20:12 Charlotte
16:35 Orlando
19:17 Charlotte
21:15 Chicago O'Hare
Connect
B6768 JetBlue Airways
F944 Frontier Airlines
22:49 Ponce
06:07 Orlando
01:43 Orlando
08:11 Chicago O'Hare
Connect
B6768 JetBlue Airways
WN4379 Southwest Airlines
22:49 Ponce
06:25 Orlando
01:43 Orlando
08:30 Chicago O'Hare
Connect
B6768 JetBlue Airways
F91154 Frontier Airlines
22:49 Ponce
06:30 Orlando
01:43 Orlando
08:34 Chicago O'Hare
Connect

References

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