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Flight from Chicago (Station) to Puerto Rico

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

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

1. Chicago Midway to San Juan

  1. You take a bus, shuttle or taxi from your location in Chicago (Station) to Chicago Midway.

  2. You take a flight from Chicago Midway to San Juan and cost approximately 270 USD.

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

Flight Depart Arrive
WN1671 Southwest Airlines
WN2194 Southwest Airlines
05:15 Chicago Midway
12:15 Orlando
08:50 Orlando
15:10 San Juan
Connect
WN4745 Southwest Airlines
WN1232 Southwest Airlines
05:25 Chicago Midway
10:55 Nashville
06:50 Nashville
15:55 San Juan
Connect
WN4673 Southwest Airlines
WN1113 Southwest Airlines
05:45 Chicago Midway
13:25 Tampa
09:15 Tampa
16:25 San Juan
Connect
DL2500 Delta
DL634 Delta
06:00 Chicago Midway
09:56 Atlanta
08:49 Atlanta
13:37 San Juan
Connect
WN1677 Southwest Airlines
WN2194 Southwest Airlines
06:20 Chicago Midway
12:15 Orlando
09:55 Orlando
15:10 San Juan
Connect
WN1206 Southwest Airlines
WN738 Southwest Airlines
06:35 Chicago Midway
12:20 Orlando
10:05 Orlando
15:15 San Juan
Connect
WN1206 Southwest Airlines
WN1718 Southwest Airlines
06:35 Chicago Midway
14:05 Orlando
10:05 Orlando
17:05 San Juan
Connect
WN1729 Southwest Airlines
WN1675 Southwest Airlines
06:45 Chicago Midway
13:50 Fort Lauderdale-Hollywood International
10:40 Fort Lauderdale-Hollywood International
16:30 San Juan
Connect
WN4758 Southwest Airlines
WN1232 Southwest Airlines
07:00 Chicago Midway
10:55 Nashville
08:25 Nashville
15:55 San Juan
Connect
WN527 Southwest Airlines
WN738 Southwest Airlines
07:40 Chicago Midway
12:20 Orlando
11:10 Orlando
15:15 San Juan
Connect
WN527 Southwest Airlines
WN1718 Southwest Airlines
07:40 Chicago Midway
14:05 Orlando
11:10 Orlando
17:05 San Juan
Connect
WN2661 Southwest Airlines
08:10 Chicago Midway
13:50 San Juan Direct
WN3388 Southwest Airlines
WN4632 Southwest Airlines
08:10 Chicago Midway
15:50 Orlando
11:40 Orlando
18:45 San Juan
Connect
WN1699 Southwest Airlines
WN2813 Southwest Airlines
10:50 Chicago Midway
17:10 Orlando
14:25 Orlando
20:05 San Juan
Connect
WN2593 Southwest Airlines
WN4561 Southwest Airlines
11:20 Chicago Midway
15:15 Baltimore
14:05 Baltimore
19:20 San Juan
Connect
WN1500 Southwest Airlines
WN4318 Southwest Airlines
11:35 Chicago Midway
19:15 Orlando
15:05 Orlando
22:10 San Juan
Connect
WN1347 Southwest Airlines
WN2427 Southwest Airlines
12:55 Chicago Midway
20:00 Tampa
16:25 Tampa
23:00 San Juan
Connect
WN3202 Southwest Airlines
WN4318 Southwest Airlines
13:30 Chicago Midway
19:15 Orlando
17:05 Orlando
22:10 San Juan
Connect
WN3202 Southwest Airlines
WN2599 Southwest Airlines
13:30 Chicago Midway
22:00 Orlando
17:05 Orlando
00:50 San Juan
Connect
WN3402 Southwest Airlines
WN1927 Southwest Airlines
14:35 Chicago Midway
20:55 Fort Lauderdale-Hollywood International
18:40 Fort Lauderdale-Hollywood International
23:35 San Juan
Connect
WN235 Southwest Airlines
WN2361 Southwest Airlines
15:00 Chicago Midway
21:40 Fort Lauderdale-Hollywood International
19:05 Fort Lauderdale-Hollywood International
00:20 San Juan
Connect
WN594 Southwest Airlines
WN1701 Southwest Airlines
15:05 Chicago Midway
21:40 Orlando
18:45 Orlando
00:30 San Juan
Connect
WN3367 Southwest Airlines
WN2599 Southwest Airlines
16:15 Chicago Midway
22:00 Orlando
19:55 Orlando
00:50 San Juan
Connect
WN947 Southwest Airlines
WN1701 Southwest Airlines
17:10 Chicago Midway
21:40 Orlando
20:45 Orlando
00:30 San Juan
Connect
WN3084 Southwest Airlines
WN1716 Southwest Airlines
21:55 Chicago Midway
06:05 Orlando
01:25 Orlando
09:00 San Juan
Connect
WN3084 Southwest Airlines
WN486 Southwest Airlines
21:55 Chicago Midway
06:20 Orlando
01:25 Orlando
09:15 San Juan
Connect

2. Chicago O'Hare to San Juan

  1. You take a bus, shuttle or taxi from your location in Chicago (Station) to Chicago O'Hare.

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

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

Flight Depart Arrive
AA328 American Airlines
AA2481 American Airlines
05:00 Chicago O'Hare
08:40 Dallas/Ft.Worth
07:21 Dallas/Ft.Worth
14:35 San Juan
Connect
AA2341 American Airlines
AA1790 American Airlines
05:07 Chicago O'Hare
12:15 Miami
09:09 Miami
15:14 San Juan
Connect
AA2341 American Airlines
AA1613 American Airlines
05:07 Chicago O'Hare
10:10 Miami
09:09 Miami
12:53 San Juan
Connect
DL2825 Delta
DL634 Delta
05:30 Chicago O'Hare
09:56 Atlanta
08:20 Atlanta
13:37 San Juan
Connect
AA1784 American Airlines
AA1852 American Airlines
05:30 Chicago O'Hare
11:00 Charlotte
08:25 Charlotte
14:42 San Juan
Connect
B6563 JetBlue Airways
B6353 JetBlue Airways
05:40 Chicago O'Hare
12:37 Fort Lauderdale-Hollywood International
09:40 Fort Lauderdale-Hollywood International
15:15 San Juan
Connect
UA2246 United Airlines
UA1192 United Airlines
06:00 Chicago O'Hare
09:48 Houston
08:41 Houston
15:20 San Juan
Connect
AA2507 American Airlines
AA1790 American Airlines
07:05 Chicago O'Hare
12:15 Miami
11:08 Miami
15:14 San Juan
Connect
DL5807 Delta
DL806 Delta
07:10 Chicago O'Hare
12:29 New York JFK
10:27 New York JFK
16:24 San Juan
Connect
AA1058 American Airlines
AA967 American Airlines
08:29 Chicago O'Hare
15:30 Miami
12:32 Miami
18:10 San Juan
Connect
WN2545 Southwest Airlines
WN4632 Southwest Airlines
08:40 Chicago O'Hare
15:50 Orlando
12:20 Orlando
18:45 San Juan
Connect
AA649 American Airlines
08:45 Chicago O'Hare
14:28 San Juan Direct
AA1150 American Airlines
AA559 American Airlines
10:22 Chicago O'Hare
16:50 Charlotte
13:16 Charlotte
20:37 San Juan
Connect
AA2322 American Airlines
AA2011 American Airlines
10:30 Chicago O'Hare
14:35 Dallas/Ft.Worth
12:49 Dallas/Ft.Worth
20:16 San Juan
Connect
B6906 JetBlue Airways
B6703 JetBlue Airways
10:30 Chicago O'Hare
16:59 New York JFK
13:58 New York JFK
20:54 San Juan
Connect
NK929 Spirit Airlines
NK880 Spirit Airlines
10:38 Chicago O'Hare
18:06 Orlando
14:28 Orlando
21:02 San Juan
Connect
NK929 Spirit Airlines
NK318 Spirit Airlines
10:38 Chicago O'Hare
15:57 Orlando
14:28 Orlando
18:53 San Juan
Connect
NK929 Spirit Airlines
NK802 Spirit Airlines
10:38 Chicago O'Hare
15:28 Orlando
14:28 Orlando
18:24 San Juan
Connect
UA2176 United Airlines
3M123 Silver Airways
10:44 Chicago O'Hare
18:00 Charlotte Amalie
16:36 Charlotte Amalie
18:35 San Juan
Connect
UA695 United Airlines
10:54 Chicago O'Hare
16:46 San Juan Direct
DL2435 Delta
DL1861 Delta
12:10 Chicago O'Hare
18:50 Atlanta
15:05 Atlanta
22:27 San Juan
Connect
AA2013 American Airlines
AA1650 American Airlines
12:19 Chicago O'Hare
19:00 Miami
16:20 Miami
21:42 San Juan
Connect
AA2013 American Airlines
AA395 American Airlines
12:19 Chicago O'Hare
19:57 Miami
16:20 Miami
22:54 San Juan
Connect
AA1984 American Airlines
AA559 American Airlines
12:25 Chicago O'Hare
16:50 Charlotte
15:18 Charlotte
20:37 San Juan
Connect
WN3126 Southwest Airlines
WN4318 Southwest Airlines
12:35 Chicago O'Hare
19:15 Orlando
16:15 Orlando
22:10 San Juan
Connect
UA2195 United Airlines
UA335 United Airlines
12:52 Chicago O'Hare
18:10 Houston
15:40 Houston
23:43 San Juan
Connect
UA224 United Airlines
UA1543 United Airlines
13:13 Chicago O'Hare
19:57 Newark
16:35 Newark
23:55 San Juan
Connect
WN4506 Southwest Airlines
WN3288 Southwest Airlines
13:30 Chicago O'Hare
19:45 Baltimore
16:25 Baltimore
23:50 San Juan
Connect
WN2860 Southwest Airlines
WN1701 Southwest Airlines
13:45 Chicago O'Hare
21:40 Orlando
17:25 Orlando
00:30 San Juan
Connect
WN2733 Southwest Airlines
WN2361 Southwest Airlines
13:50 Chicago O'Hare
21:40 Fort Lauderdale-Hollywood International
17:55 Fort Lauderdale-Hollywood International
00:20 San Juan
Connect
UA2197 United Airlines
UA335 United Airlines
14:02 Chicago O'Hare
18:10 Houston
16:57 Houston
23:43 San Juan
Connect
AA2565 American Airlines
AA395 American Airlines
14:16 Chicago O'Hare
19:57 Miami
18:30 Miami
22:54 San Juan
Connect
AA2840 American Airlines
AA2294 American Airlines
14:55 Chicago O'Hare
19:04 Philadelphia
17:50 Philadelphia
23:11 San Juan
Connect
UA378 United Airlines
UA1543 United Airlines
14:58 Chicago O'Hare
19:57 Newark
18:19 Newark
23:55 San Juan
Connect
B61106 JetBlue Airways
B6903 JetBlue Airways
15:57 Chicago O'Hare
21:15 New York JFK
19:30 New York JFK
01:07 San Juan
Connect
B61106 JetBlue Airways
B62103 JetBlue Airways
15:57 Chicago O'Hare
22:29 New York JFK
19:30 New York JFK
02:22 San Juan
Connect
UA2161 United Airlines
UA701 United Airlines
15:59 Chicago O'Hare
19:40 Houston
18:48 Houston
01:13 San Juan
Connect
WN2925 Southwest Airlines
WN2279 Southwest Airlines
17:00 Chicago O'Hare
20:55 Baltimore
20:00 Baltimore
01:00 San Juan
Connect
UA2170 United Airlines
UA2023 United Airlines
18:00 Chicago O'Hare
22:20 Washington Dulles
20:56 Washington Dulles
02:19 San Juan
Connect
AA1890 American Airlines
23:19 Chicago O'Hare
05:00 San Juan Direct

3. Chicago O'Hare to Mayaguez

  1. You take a bus, shuttle or taxi from your location in Chicago (Station) to Chicago O'Hare.

  2. You take a flight from Chicago O'Hare to Mayaguez and cost approximately 650 USD.

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

Flight Depart Arrive
B6563 JetBlue Airways
B6353 JetBlue Airways
9K40 Cape Air
05:40 Chicago O'Hare
12:37 Fort Lauderdale-Hollywood International
16:19 San Juan
09:40 Fort Lauderdale-Hollywood International
15:15 San Juan
16:56 Mayaguez
Connect
B6563 JetBlue Airways
B6353 JetBlue Airways
9K41 Cape Air
05:40 Chicago O'Hare
12:37 Fort Lauderdale-Hollywood International
18:18 San Juan
09:40 Fort Lauderdale-Hollywood International
15:15 San Juan
18:55 Mayaguez
Connect
UA2246 United Airlines
UA1192 United Airlines
9K41 Cape Air
06:00 Chicago O'Hare
09:48 Houston
18:18 San Juan
08:41 Houston
15:20 San Juan
18:55 Mayaguez
Connect
UA2246 United Airlines
UA1192 United Airlines
9K40 Cape Air
06:00 Chicago O'Hare
09:48 Houston
16:19 San Juan
08:41 Houston
15:20 San Juan
16:56 Mayaguez
Connect
AA2507 American Airlines
AA1790 American Airlines
9K40 Cape Air
07:05 Chicago O'Hare
12:15 Miami
16:19 San Juan
11:08 Miami
15:14 San Juan
16:56 Mayaguez
Connect
AA1872 American Airlines
B61589 JetBlue Airways
9K41 Cape Air
07:07 Chicago O'Hare
12:10 Newark
18:18 San Juan
10:08 Newark
16:09 San Juan
18:55 Mayaguez
Connect
AA649 American Airlines
9K41 Cape Air
08:45 Chicago O'Hare
18:18 San Juan
14:28 San Juan
18:55 Mayaguez
Connect
AA649 American Airlines
9K40 Cape Air
08:45 Chicago O'Hare
16:19 San Juan
14:28 San Juan
16:56 Mayaguez
Connect
UA695 United Airlines
9K41 Cape Air
10:54 Chicago O'Hare
18:18 San Juan
16:46 San Juan
18:55 Mayaguez
Connect
UA2170 United Airlines
UA2023 United Airlines
9K34 Cape Air
18:00 Chicago O'Hare
22:20 Washington Dulles
09:22 San Juan
20:56 Washington Dulles
02:19 San Juan
09:59 Mayaguez
Connect
AA1890 American Airlines
9K34 Cape Air
23:19 Chicago O'Hare
09:22 San Juan
05:00 San Juan
09:59 Mayaguez
Connect

4. Chicago O'Hare to Ponce

  1. You take a bus, shuttle or taxi from your location in Chicago (Station) to Chicago O'Hare.

  2. You take a flight from Chicago O'Hare to Ponce and cost approximately 950 USD.

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

Flight Depart Arrive
NK2814 Spirit Airlines
NK554 Spirit Airlines
B6767 JetBlue Airways
11:10 Chicago O'Hare
14:27 New Orleans
19:10 Orlando
13:35 New Orleans
17:21 Orlando
22:04 Ponce
Connect
UA2340 United Airlines
B6767 JetBlue Airways
11:10 Chicago O'Hare
19:10 Orlando
15:01 Orlando
22:04 Ponce
Connect
AA532 American Airlines
B6745 JetBlue Airways
11:38 Chicago O'Hare
22:59 New York JFK
14:55 New York JFK
03:09 Ponce
Connect
DL2435 Delta
DL866 Delta
B6767 JetBlue Airways
12:10 Chicago O'Hare
16:15 Atlanta
19:10 Orlando
15:05 Atlanta
17:55 Orlando
22:04 Ponce
Connect
AA1984 American Airlines
AA1682 American Airlines
B6767 JetBlue Airways
12:25 Chicago O'Hare
16:22 Charlotte
19:10 Orlando
15:18 Charlotte
18:00 Orlando
22:04 Ponce
Connect
WN3126 Southwest Airlines
B6767 JetBlue Airways
12:35 Chicago O'Hare
19:10 Orlando
16:15 Orlando
22:04 Ponce
Connect
WN2860 Southwest Airlines
B6767 JetBlue Airways
13:45 Chicago O'Hare
19:10 Orlando
17:25 Orlando
22:04 Ponce
Connect
DL5244 Delta
B6745 JetBlue Airways
14:25 Chicago O'Hare
22:59 New York JFK
17:59 New York JFK
03:09 Ponce
Connect
B61106 JetBlue Airways
B6745 JetBlue Airways
15:57 Chicago O'Hare
22:59 New York JFK
19:30 New York JFK
03:09 Ponce
Connect
DL5381 Delta
B6745 JetBlue Airways
18:00 Chicago O'Hare
22:59 New York JFK
21:37 New York JFK
03:09 Ponce
Connect
AA2518 American Airlines
B6745 JetBlue Airways
18:04 Chicago O'Hare
22:59 New York JFK
21:29 New York JFK
03:09 Ponce
Connect

References

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