Take off on cheap flights from Chicago to Havana, your adventure starts now!

Find cheap airline tickets from Chicago to Havana by date

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  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • any
  • May 2018
  • June 2018
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • price
  • month of departure
  • month of return
$273
outward: Nov 6, 2018
1:25a ORD » 2:15p HAV
American Airlines 2 stops (12h50m)
inbound: Nov 10, 2018
7:00p HAV » 3:46p ORD
American Airlines 1 stop (20h46m)
$274
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 11, 2019
7:00p HAV » 4:13a ORD
American Airlines 1 stop (9h13m)
$274
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 11, 2019
7:00p HAV » 6:43a ORD
American Airlines 1 stop (11h43m)
$278
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 12, 2019
7:00p HAV » 4:13a ORD
American Airlines 1 stop (9h13m)
$279
outward: Jun 1, 2018
7:35p ORD » 5:15p HAV
American Airlines 1 stop (21h40m)
inbound: Jun 5, 2018
6:15p HAV » 6:50a ORD
American Airlines 1 stop (12h35m)
$281
outward: Jan 2, 2019
2:00p ORD » 3:10a HAV
American Airlines 2 stops (13h10m)
inbound: Jan 11, 2019
7:00p HAV » 2:15a ORD
American Airlines 1 stop (7h15m)
$283
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 11, 2019
7:00p HAV » 5:16a ORD
American Airlines 2 stops (10h16m)
$283
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 12, 2019
7:00p HAV » 9:32p ORD
American Airlines 1 stop (26h32m)
$283
outward: Jan 2, 2019
2:00p ORD » 3:10a HAV
American Airlines 2 stops (13h10m)
inbound: Jan 12, 2019
7:00p HAV » 5:20a ORD
American Airlines 2 stops (10h20m)
$284
outward: Sep 15, 2018
1:15a ORD » 10:30p HAV
Unknown Company 1 stop (21h15m)
inbound: Sep 17, 2018
8:50p HAV » 4:49a ORD
United Airlines 1 stop (7h59m)
$315
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 12, 2019
7:00p HAV » 5:52p ORD
American Airlines 1 stop (22h52m)
$316
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 12, 2019
7:00p HAV » 5:52p ORD
American Airlines 1 stop (22h52m)
$316
outward: Jan 2, 2019
6:50p ORD » 3:10a HAV
American Airlines 2 stops (8h20m)
inbound: Jan 12, 2019
7:00p HAV » 3:46p ORD
American Airlines 1 stop (20h46m)
$317
outward: Jan 2, 2019
6:50p ORD » 3:10a HAV
American Airlines 2 stops (8h20m)
inbound: Jan 12, 2019
7:00p HAV » 4:13a ORD
American Airlines 1 stop (9h13m)
$317
outward: Jan 2, 2019
12:00p ORD » 3:10a HAV
American Airlines 2 stops (15h10m)
inbound: Jan 12, 2019
7:00p HAV » 5:52p ORD
American Airlines 1 stop (22h52m)
$318
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 12, 2019
7:00p HAV » 3:46p ORD
American Airlines 1 stop (20h46m)
$318
outward: Jan 2, 2019
2:00p ORD » 3:10a HAV
American Airlines 2 stops (13h10m)
inbound: Jan 12, 2019
7:00p HAV » 5:20a ORD
American Airlines 2 stops (10h20m)
$318
outward: Jan 2, 2019
6:50p ORD » 3:10a HAV
American Airlines 2 stops (8h20m)
inbound: Jan 12, 2019
7:00p HAV » 2:40p ORD
American Airlines 2 stops (19h40m)
$318
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 12, 2019
7:00p HAV » 5:20a ORD
American Airlines 2 stops (10h20m)
$321
outward: Jan 2, 2019
2:00p ORD » 3:10a HAV
American Airlines 2 stops (13h10m)
inbound: Jan 12, 2019
7:00p HAV » 4:13a ORD
American Airlines 1 stop (9h13m)
$321
outward: Jan 2, 2019
2:00p ORD » 3:10a HAV
American Airlines 2 stops (13h10m)
inbound: Jan 12, 2019
7:00p HAV » 5:20a ORD
American Airlines 2 stops (10h20m)
$321
outward: Jan 2, 2019
6:50p ORD » 3:10a HAV
American Airlines 2 stops (8h20m)
inbound: Jan 12, 2019
7:00p HAV » 9:32p ORD
American Airlines 1 stop (26h32m)
$321
outward: Jan 2, 2019
6:50p ORD » 3:10a HAV
American Airlines 2 stops (8h20m)
inbound: Jan 12, 2019
7:00p HAV » 9:32p ORD
American Airlines 1 stop (26h32m)
$321
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 12, 2019
7:00p HAV » 2:15a ORD
American Airlines 1 stop (7h15m)
$322
outward: Jan 2, 2019
6:50p ORD » 3:10a HAV
American Airlines 2 stops (8h20m)
inbound: Jan 12, 2019
7:00p HAV » 4:13a ORD
American Airlines 1 stop (9h13m)
$322
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 12, 2019
7:00p HAV » 2:15a ORD
American Airlines 1 stop (7h15m)
$322
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 12, 2019
7:00p HAV » 2:15a ORD
American Airlines 1 stop (7h15m)
$323
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 12, 2019
7:00p HAV » 5:20a ORD
American Airlines 2 stops (10h20m)
$323
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 12, 2019
7:00p HAV » 2:40p ORD
American Airlines 2 stops (19h40m)
$323
outward: Jan 2, 2019
3:50p ORD » 3:10a HAV
American Airlines 2 stops (11h20m)
inbound: Jan 12, 2019
7:00p HAV » 9:32p ORD
American Airlines 1 stop (26h32m)
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$484 $526 $526
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$493 $335 $337
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$493 $520 $520
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Choose when you'd like to depart to Havana (Cuba):
Find the cheapest Chicago Havana flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Chicago - Havana with these new dates, click on an offer. Want to depart from another city? Choose: New York - Havana London - Havana Miami - Havana See more routes

Airlines operating flights from Chicago to Havana

Sorry! We haven't found any airline tickets from Chicago to Havana. Try launching another search above.

Travel tips for flights Chicago - Havana

Average flight duration: 17h43m (flight with stopovers)

  • Arrival city:
  • Havana, Cuba
  • Airport(s):
  • José Martí International Airport (HAV)
  • Playa Baracoa Airport (UPB)
  • Local time:
  • May 26, 2018 7:42 PM, GMT-4
  • Weather:
  • min. 66ºF, max. 78ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • May 26, 2018 6:42 PM, GMT-5
  • Weather:
  • min. 65ºF, max. 84ºF