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Flight from Chicago to Cuba

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

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

1. Chicago Midway to Havana

  1. You take a flight from Chicago Midway to Havana and cost approximately 360 USD.

  2. You take a bus, shuttle or taxi from Havana to your destination in Cuba.

Flight Depart Arrive
WN3448 Southwest Airlines
WN3922 Southwest Airlines
05:05 Chicago Midway
12:25 Fort Lauderdale
09:05 Fort Lauderdale
13:50 Havana
Connect
WN3508 Southwest Airlines
WN3922 Southwest Airlines
05:10 Chicago Midway
12:25 Fort Lauderdale
09:10 Fort Lauderdale
13:50 Havana
Connect
WN2282 Southwest Airlines
WN5906 Southwest Airlines
05:15 Chicago Midway
10:50 Tampa
08:35 Tampa
12:10 Havana
Connect
WN5151 Southwest Airlines
WN3922 Southwest Airlines
05:35 Chicago Midway
12:25 Fort Lauderdale
09:35 Fort Lauderdale
13:50 Havana
Connect
WN5151 Southwest Airlines
WN3920 Southwest Airlines
05:35 Chicago Midway
15:05 Fort Lauderdale
09:35 Fort Lauderdale
16:35 Havana
Connect
WN887 Southwest Airlines
DL5201 Delta
05:45 Chicago Midway
11:15 Atlanta
08:35 Atlanta
13:35 Havana
Connect
DL2030 Delta
DL5201 Delta
06:00 Chicago Midway
11:15 Atlanta
08:52 Atlanta
13:35 Havana
Connect
WN2577 Southwest Airlines
DL5201 Delta
07:00 Chicago Midway
11:15 Atlanta
10:00 Atlanta
13:35 Havana
Connect
WN3470 Southwest Airlines
DL5201 Delta
07:00 Chicago Midway
11:15 Atlanta
09:50 Atlanta
13:35 Havana
Connect
DL2701 Delta
DL5201 Delta
07:15 Chicago Midway
11:15 Atlanta
10:08 Atlanta
13:35 Havana
Connect
WN3736 Southwest Airlines
WN3920 Southwest Airlines
07:35 Chicago Midway
15:05 Fort Lauderdale
11:40 Fort Lauderdale
16:35 Havana
Connect
DL3928 Delta
DL2535 Delta
DL513 Delta
09:15 Chicago Midway
12:33 Detroit
18:12 Miami
11:29 Detroit
15:33 Miami
19:30 Havana
Connect
WN3167 Southwest Airlines
WN3920 Southwest Airlines
09:55 Chicago Midway
15:05 Fort Lauderdale
13:55 Fort Lauderdale
16:35 Havana
Connect
WN4822 Southwest Airlines
WN4990 Southwest Airlines
WN3952 Southwest Airlines
20:05 Chicago Midway
22:30 Nashville
07:00 Tampa
21:30 Nashville
01:05 Tampa
08:15 Havana
Connect
WN3044 Southwest Airlines
WN3952 Southwest Airlines
20:55 Chicago Midway
07:00 Tampa
00:20 Tampa
08:15 Havana
Connect
WN5969 Southwest Airlines
WN3952 Southwest Airlines
21:35 Chicago Midway
07:00 Tampa
01:00 Tampa
08:15 Havana
Connect
WN3561 Southwest Airlines
WN3952 Southwest Airlines
21:35 Chicago Midway
07:00 Tampa
01:05 Tampa
08:15 Havana
Connect
WN1029 Southwest Airlines
WN4308 Southwest Airlines
WN3924 Southwest Airlines
22:10 Chicago Midway
06:25 Raleigh/Durham
09:25 Fort Lauderdale
00:55 Raleigh/Durham
08:30 Fort Lauderdale
10:50 Havana
Connect

2. Chicago O'Hare to Havana

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

  2. You take a bus, shuttle or taxi from Havana to your destination in Cuba.

Flight Depart Arrive
4O2983 Interjet
4O2904 Interjet
01:25 Chicago O'Hare
07:30 Mexico City
05:35 Mexico City
11:20 Havana
Connect
B6563 JetBlue Airways
B61899 JetBlue Airways
05:09 Chicago O'Hare
15:05 Fort Lauderdale
09:10 Fort Lauderdale
16:25 Havana
Connect
B6563 JetBlue Airways
B61499 JetBlue Airways
05:09 Chicago O'Hare
12:25 Fort Lauderdale
09:10 Fort Lauderdale
13:45 Havana
Connect
AA1411 American Airlines
AA2705 American Airlines
05:36 Chicago O'Hare
10:40 Miami
09:40 Miami
11:50 Havana
Connect
UA3934 United Airlines
DL5201 Delta
06:00 Chicago O'Hare
11:15 Atlanta
08:53 Atlanta
13:35 Havana
Connect
UA1754 United Airlines
UA6306 United Airlines
06:00 Chicago O'Hare
11:59 Houston
08:45 Houston
16:15 Havana
Connect
UA1754 United Airlines
UA1506 United Airlines
06:00 Chicago O'Hare
11:56 Houston
08:45 Houston
15:35 Havana
Connect
UA675 United Airlines
UA3542 United Airlines
06:00 Chicago O'Hare
10:04 Newark
09:11 Newark
13:55 Havana
Connect
B6412 JetBlue Airways
B6867 JetBlue Airways
06:29 Chicago O'Hare
12:31 Boston
09:55 Boston
16:30 Havana
Connect
AA2498 American Airlines
AA837 American Airlines
06:30 Chicago O'Hare
15:30 Miami
10:34 Miami
16:50 Havana
Connect
AA2379 American Airlines
B61499 JetBlue Airways
07:00 Chicago O'Hare
12:25 Fort Lauderdale
10:57 Fort Lauderdale
13:45 Havana
Connect
AA4213 American Airlines
AA4630 American Airlines
AA1345 American Airlines
07:00 Chicago O'Hare
12:17 Jacksonville
17:00 Miami
10:21 Jacksonville
13:40 Miami
18:15 Havana
Connect
AA2507 American Airlines
AA1345 American Airlines
07:00 Chicago O'Hare
17:00 Miami
11:04 Miami
18:15 Havana
Connect
AA2507 American Airlines
AA837 American Airlines
07:00 Chicago O'Hare
15:30 Miami
11:04 Miami
16:50 Havana
Connect
AA2379 American Airlines
WN3922 Southwest Airlines
07:00 Chicago O'Hare
12:25 Fort Lauderdale
10:57 Fort Lauderdale
13:50 Havana
Connect
DL379 Delta
DL5201 Delta
07:00 Chicago O'Hare
11:15 Atlanta
09:53 Atlanta
13:35 Havana
Connect
DL3153 Delta
DL5201 Delta
07:00 Chicago O'Hare
11:15 Atlanta
09:55 Atlanta
13:35 Havana
Connect
AA4213 American Airlines
AA4630 American Airlines
AA837 American Airlines
07:00 Chicago O'Hare
12:17 Jacksonville
15:30 Miami
10:21 Jacksonville
13:40 Miami
16:50 Havana
Connect
DL3153 Delta
DL5201 Delta
07:10 Chicago O'Hare
11:15 Atlanta
10:05 Atlanta
13:35 Havana
Connect
AA3746 American Airlines
AA3941 American Airlines
AA1345 American Airlines
07:10 Chicago O'Hare
12:11 Charleston
17:00 Miami
10:37 Charleston
13:57 Miami
18:15 Havana
Connect
AA3746 American Airlines
AA3941 American Airlines
AA837 American Airlines
07:10 Chicago O'Hare
12:11 Charleston
15:30 Miami
10:37 Charleston
13:57 Miami
16:50 Havana
Connect
AA1452 American Airlines
DL5201 Delta
07:14 Chicago O'Hare
11:15 Atlanta
09:59 Atlanta
13:35 Havana
Connect
UA1883 United Airlines
UA6306 United Airlines
08:00 Chicago O'Hare
11:59 Houston
10:40 Houston
16:15 Havana
Connect
UA1883 United Airlines
UA1506 United Airlines
08:00 Chicago O'Hare
11:56 Houston
10:40 Houston
15:35 Havana
Connect
AA3392 American Airlines
AA4396 American Airlines
AA837 American Airlines
08:20 Chicago O'Hare
13:22 Key West
15:30 Miami
12:25 Key West
14:34 Miami
16:50 Havana
Connect
AA3392 American Airlines
AA4396 American Airlines
AA2699 American Airlines
08:20 Chicago O'Hare
13:22 Key West
18:50 Miami
12:25 Key West
14:34 Miami
20:10 Havana
Connect
AA3392 American Airlines
AA4396 American Airlines
AA1345 American Airlines
08:20 Chicago O'Hare
13:22 Key West
17:00 Miami
12:25 Key West
14:34 Miami
18:15 Havana
Connect
UA722 United Airlines
B61899 JetBlue Airways
08:30 Chicago O'Hare
15:05 Fort Lauderdale
12:47 Fort Lauderdale
16:25 Havana
Connect
AA1438 American Airlines
AA2699 American Airlines
08:35 Chicago O'Hare
18:50 Miami
12:40 Miami
20:10 Havana
Connect
AA1438 American Airlines
AA1345 American Airlines
08:35 Chicago O'Hare
17:00 Miami
12:40 Miami
18:15 Havana
Connect
AA1438 American Airlines
AA837 American Airlines
08:35 Chicago O'Hare
15:30 Miami
12:40 Miami
16:50 Havana
Connect
AC7590 Air Canada
CA879 Air China
10:40 Chicago O'Hare
15:20 Montreal
13:46 Montreal
19:35 Havana
Connect
UA532 United Airlines
AA1345 American Airlines
11:25 Chicago O'Hare
17:00 Miami
15:31 Miami
18:15 Havana
Connect
UA532 United Airlines
DL513 Delta
11:25 Chicago O'Hare
18:12 Miami
15:31 Miami
19:30 Havana
Connect
AC506 Air Canada
AC1876 Air Canada
11:35 Chicago O'Hare
20:00 Toronto
14:14 Toronto
23:30 Havana
Connect
AA335 American Airlines
AA1345 American Airlines
12:00 Chicago O'Hare
17:00 Miami
16:04 Miami
18:15 Havana
Connect
AA335 American Airlines
AA2699 American Airlines
12:00 Chicago O'Hare
18:50 Miami
16:04 Miami
20:10 Havana
Connect
AA2796 American Airlines
AA2699 American Airlines
13:35 Chicago O'Hare
18:50 Miami
17:42 Miami
20:10 Havana
Connect
AC508 Air Canada
AC1876 Air Canada
14:20 Chicago O'Hare
20:00 Toronto
16:59 Toronto
23:30 Havana
Connect
AC510 Air Canada
AC1876 Air Canada
16:20 Chicago O'Hare
20:00 Toronto
18:59 Toronto
23:30 Havana
Connect

3. Milwaukee to Havana

  1. You take a bus, shuttle or taxi from your location in Chicago to Milwaukee.

  2. You take a flight from Milwaukee to Havana and cost approximately 210 USD.

  3. You take a bus, shuttle or taxi from Havana to your destination in Cuba.

Flight Depart Arrive
WN2090 Southwest Airlines
WN57 Southwest Airlines
WN3920 Southwest Airlines
05:25 Milwaukee
10:10 Nashville
15:05 Fort Lauderdale
06:55 Nashville
13:30 Fort Lauderdale
16:35 Havana
Connect
WN2090 Southwest Airlines
WN2702 Southwest Airlines
WN3920 Southwest Airlines
05:25 Milwaukee
07:45 Nashville
15:05 Fort Lauderdale
06:55 Nashville
11:05 Fort Lauderdale
16:35 Havana
Connect
WN2090 Southwest Airlines
WN2702 Southwest Airlines
WN3922 Southwest Airlines
05:25 Milwaukee
07:45 Nashville
12:25 Fort Lauderdale
06:55 Nashville
11:05 Fort Lauderdale
13:50 Havana
Connect
AA4859 American Airlines
AA2665 American Airlines
AA1345 American Airlines
05:45 Milwaukee
10:40 Philadelphia
17:00 Miami
08:55 Philadelphia
13:39 Miami
18:15 Havana
Connect
DL2085 Delta
DL5201 Delta
05:45 Milwaukee
11:15 Atlanta
08:45 Atlanta
13:35 Havana
Connect
AA4859 American Airlines
AA2665 American Airlines
AA837 American Airlines
05:45 Milwaukee
10:40 Philadelphia
15:30 Miami
08:55 Philadelphia
13:39 Miami
16:50 Havana
Connect
WN4404 Southwest Airlines
WN5906 Southwest Airlines
05:50 Milwaukee
10:50 Tampa
09:30 Tampa
12:10 Havana
Connect
WN4404 Southwest Airlines
WN4591 Southwest Airlines
WN3920 Southwest Airlines
05:50 Milwaukee
12:40 Tampa
15:05 Fort Lauderdale
09:30 Tampa
13:55 Fort Lauderdale
16:35 Havana
Connect
WN954 Southwest Airlines
WN639 Southwest Airlines
WN3920 Southwest Airlines
06:00 Milwaukee
10:30 Atlanta
15:05 Fort Lauderdale
09:05 Atlanta
12:35 Fort Lauderdale
16:35 Havana
Connect
WN954 Southwest Airlines
DL5201 Delta
06:00 Milwaukee
11:15 Atlanta
09:05 Atlanta
13:35 Havana
Connect
WN975 Southwest Airlines
WN1437 Southwest Airlines
WN3920 Southwest Airlines
06:05 Milwaukee
11:55 Orlando
15:05 Fort Lauderdale
09:50 Orlando
13:05 Fort Lauderdale
16:35 Havana
Connect
WN3580 Southwest Airlines
WN4352 Southwest Airlines
WN3920 Southwest Airlines
06:15 Milwaukee
10:50 Nashville
15:05 Fort Lauderdale
07:45 Nashville
14:05 Fort Lauderdale
16:35 Havana
Connect
AA3261 American Airlines
AA1438 American Airlines
AA1345 American Airlines
06:24 Milwaukee
08:35 Chicago O'Hare
17:00 Miami
07:26 Chicago O'Hare
12:40 Miami
18:15 Havana
Connect
AA3261 American Airlines
AA335 American Airlines
AA1345 American Airlines
06:24 Milwaukee
12:00 Chicago O'Hare
17:00 Miami
07:26 Chicago O'Hare
16:04 Miami
18:15 Havana
Connect
AA3261 American Airlines
AA1438 American Airlines
AA837 American Airlines
06:24 Milwaukee
08:35 Chicago O'Hare
15:30 Miami
07:26 Chicago O'Hare
12:40 Miami
16:50 Havana
Connect
WN3839 Southwest Airlines
WN4936 Southwest Airlines
WN3920 Southwest Airlines
06:35 Milwaukee
11:05 Baltimore
15:05 Fort Lauderdale
09:25 Baltimore
13:50 Fort Lauderdale
16:35 Havana
Connect
WN3839 Southwest Airlines
WN3878 Southwest Airlines
WN3920 Southwest Airlines
06:35 Milwaukee
10:55 Baltimore
15:05 Fort Lauderdale
09:25 Baltimore
13:35 Fort Lauderdale
16:35 Havana
Connect
WN3575 Southwest Airlines
DL5201 Delta
06:45 Milwaukee
11:15 Atlanta
09:50 Atlanta
13:35 Havana
Connect
DL2539 Delta
DL5201 Delta
07:00 Milwaukee
11:15 Atlanta
10:00 Atlanta
13:35 Havana
Connect
AA3210 American Airlines
AA335 American Airlines
AA1345 American Airlines
08:08 Milwaukee
12:00 Chicago O'Hare
17:00 Miami
09:09 Chicago O'Hare
16:04 Miami
18:15 Havana
Connect
AA3210 American Airlines
AA2796 American Airlines
AA2699 American Airlines
08:08 Milwaukee
13:35 Chicago O'Hare
18:50 Miami
09:09 Chicago O'Hare
17:42 Miami
20:10 Havana
Connect
AA3210 American Airlines
AA335 American Airlines
AA2699 American Airlines
08:08 Milwaukee
12:00 Chicago O'Hare
18:50 Miami
09:09 Chicago O'Hare
16:04 Miami
20:10 Havana
Connect
UA5599 United Airlines
UA1506 United Airlines
08:21 Milwaukee
11:56 Houston
10:58 Houston
15:35 Havana
Connect
UA5599 United Airlines
UA6306 United Airlines
08:21 Milwaukee
11:59 Houston
10:58 Houston
16:15 Havana
Connect
DL764 Delta
DL1224 Delta
DL513 Delta
10:00 Milwaukee
13:59 Atlanta
18:12 Miami
13:00 Atlanta
15:59 Miami
19:30 Havana
Connect
DL764 Delta
DL1998 Delta
DL513 Delta
10:00 Milwaukee
15:11 Atlanta
18:12 Miami
13:00 Atlanta
17:15 Miami
19:30 Havana
Connect
AA3069 American Airlines
AA2796 American Airlines
AA2699 American Airlines
11:16 Milwaukee
13:35 Chicago O'Hare
18:50 Miami
12:15 Chicago O'Hare
17:42 Miami
20:10 Havana
Connect
DL2941 Delta
DL1998 Delta
DL513 Delta
11:19 Milwaukee
15:11 Atlanta
18:12 Miami
14:20 Atlanta
17:15 Miami
19:30 Havana
Connect
WN6155 Southwest Airlines
WN3952 Southwest Airlines
20:00 Milwaukee
07:00 Tampa
23:35 Tampa
08:15 Havana
Connect

4. Chicago O'Hare to Santa Clara

  1. You take a flight from Chicago O'Hare to Santa Clara and cost approximately 250 USD.

  2. You take a bus, shuttle or taxi from Santa Clara to your destination in Cuba.

Flight Depart Arrive
4O2983 Interjet
4O3950 Interjet
01:25 Chicago O'Hare
07:55 Mexico City
05:35 Mexico City
11:55 Santa Clara
Connect
UA4362 United Airlines
TS554 Air Transat
06:00 Chicago O'Hare
13:00 Montreal
09:12 Montreal
16:55 Santa Clara
Connect
UA4362 United Airlines
TS912 Air Transat
06:00 Chicago O'Hare
12:05 Montreal
09:12 Montreal
16:00 Santa Clara
Connect
UA5672 United Airlines
AC7944 Air Canada
AC1764 Air Canada
06:00 Chicago O'Hare
10:05 Indianapolis
16:10 Toronto
08:01 Indianapolis
11:41 Toronto
19:35 Santa Clara
Connect
AC7598 Air Canada
TS912 Air Transat
06:30 Chicago O'Hare
12:05 Montreal
09:36 Montreal
16:00 Santa Clara
Connect
AC7598 Air Canada
TS554 Air Transat
06:30 Chicago O'Hare
13:00 Montreal
09:36 Montreal
16:55 Santa Clara
Connect
UA5551 United Airlines
AC8916 Air Canada
AC1764 Air Canada
06:30 Chicago O'Hare
10:35 Detroit
16:10 Toronto
08:50 Detroit
11:45 Toronto
19:35 Santa Clara
Connect
UA3696 United Airlines
AC8926 Air Canada
AC1764 Air Canada
06:44 Chicago O'Hare
10:45 Covington
16:10 Toronto
08:57 Covington
12:19 Toronto
19:35 Santa Clara
Connect
AC502 Air Canada
AC1764 Air Canada
08:05 Chicago O'Hare
16:10 Toronto
10:44 Toronto
19:35 Santa Clara
Connect
AA3102 American Airlines
TS554 Air Transat
08:20 Chicago O'Hare
13:00 Montreal
11:37 Montreal
16:55 Santa Clara
Connect
UA4609 United Airlines
AC1764 Air Canada
08:55 Chicago O'Hare
16:10 Toronto
11:24 Toronto
19:35 Santa Clara
Connect
AC504 Air Canada
AC1764 Air Canada
09:55 Chicago O'Hare
16:10 Toronto
12:34 Toronto
19:35 Santa Clara
Connect
AC7590 Air Canada
TS714 Air Transat
10:40 Chicago O'Hare
16:15 Montreal
13:46 Montreal
20:05 Santa Clara
Connect
UA3632 United Airlines
TS504 Air Transat
11:25 Chicago O'Hare
16:50 Quebec
15:05 Quebec
21:05 Santa Clara
Connect
AC506 Air Canada
AC1764 Air Canada
11:35 Chicago O'Hare
16:10 Toronto
14:14 Toronto
19:35 Santa Clara
Connect
UA4370 United Airlines
AC1764 Air Canada
11:40 Chicago O'Hare
16:10 Toronto
14:06 Toronto
19:35 Santa Clara
Connect
AA3080 American Airlines
AC1764 Air Canada
11:55 Chicago O'Hare
16:10 Toronto
14:33 Toronto
19:35 Santa Clara
Connect
AC7592 Air Canada
TS714 Air Transat
12:15 Chicago O'Hare
16:15 Montreal
15:21 Montreal
20:05 Santa Clara
Connect
AC7596 Air Canada
AC1768 Air Canada
19:35 Chicago O'Hare
07:00 Montreal
22:41 Montreal
10:50 Santa Clara
Connect

References

Find Hotels in Cuba

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

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