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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  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • any
  • July 2018
  • August 2018
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • price
  • month of departure
  • month of return
$352
outward: Jan 3, 2019
4:10a ORD » 7:50p HAV
United Airlines 1 stop (15h40m)
inbound: Jan 12, 2019
8:35p HAV » 6:42p ORD
Delta Air Lines 1 stop (22h07m)
$354
outward: Jan 2, 2019
5:43p ORD » 7:50p HAV
United Airlines 1 stop (26h07m)
inbound: Jan 12, 2019
8:50p HAV » 1:49p ORD
United Airlines 1 stop (16h59m)
$354
outward: Jan 2, 2019
5:43p ORD » 7:50p HAV
United Airlines 1 stop (26h07m)
inbound: Jan 12, 2019
8:50p HAV » 1:49p ORD
United Airlines 1 stop (16h59m)
$358
outward: Jan 3, 2019
4:10a ORD » 7:50p HAV
United Airlines 1 stop (15h40m)
inbound: Jan 12, 2019
8:50p HAV » 3:05p ORD
United Airlines 1 stop (18h15m)
$360
outward: Jan 3, 2019
2:30a ORD » 7:50p HAV
United Airlines 1 stop (17h20m)
inbound: Jan 12, 2019
8:50p HAV » 1:49p ORD
United Airlines 1 stop (16h59m)
$360
outward: Jan 2, 2019
4:02p ORD » 7:50p HAV
United Airlines 1 stop (27h48m)
inbound: Jan 12, 2019
8:50p HAV » 1:49p ORD
United Airlines 1 stop (16h59m)
$361
outward: Jan 3, 2019
4:10a ORD » 7:50p HAV
United Airlines 1 stop (15h40m)
inbound: Jan 12, 2019
8:50p HAV » 3:05p ORD
United Airlines 1 stop (18h15m)
$363
outward: Jan 3, 2019
2:30a ORD » 7:50p HAV
United Airlines 1 stop (17h20m)
inbound: Jan 12, 2019
8:50p HAV » 1:49p ORD
United Airlines 1 stop (16h59m)
$380
outward: Jan 2, 2019
8:40a ORD » 4:30a HAV
Aeromexico 2 stops (19h50m)
inbound: Jan 12, 2019
12:10p HAV » 6:59a ORD
Aeromexico 2 stops (18h49m)
$398
outward: Jan 3, 2019
4:10a ORD » 7:50p HAV
United Airlines 1 stop (15h40m)
inbound: Jan 12, 2019
8:50p HAV » 1:49p ORD
United Airlines 1 stop (16h59m)
$408
outward: Jan 2, 2019
2:00p ORD » 10:30p HAV
JetBlue 1 stop (8h30m)
inbound: Jan 12, 2019
9:00p HAV » 6:38a ORD
JetBlue 1 stop (9h38m)
$408
outward: Jan 2, 2019
2:00p ORD » 7:45p HAV
JetBlue 1 stop (5h45m)
inbound: Jan 12, 2019
9:00p HAV » 6:38a ORD
JetBlue 1 stop (9h38m)
$409
outward: Jan 2, 2019
2:00p ORD » 7:45p HAV
JetBlue 1 stop (5h45m)
inbound: Jan 12, 2019
9:00p HAV » 6:38a ORD
JetBlue 1 stop (9h38m)
$409
outward: Jan 2, 2019
2:00p ORD » 7:45p HAV
JetBlue 1 stop (5h45m)
inbound: Jan 12, 2019
9:00p HAV » 6:38a ORD
JetBlue 1 stop (9h38m)
$411
outward: Jan 2, 2019
2:00p ORD » 7:45p HAV
JetBlue 1 stop (5h45m)
inbound: Jan 12, 2019
9:00p HAV » 6:38a ORD
JetBlue 1 stop (9h38m)
$423
outward: Jan 2, 2019
5:30p MDW » 7:35p HAV
Delta Air Lines 2 stops (26h05m)
inbound: Jan 12, 2019
8:35p HAV » 6:42p ORD
Delta Air Lines 1 stop (22h07m)
$438
outward: Jan 2, 2019
3:10p ORD » 4:20p HAV
Delta Air Lines 2 stops (25h10m)
inbound: Jan 12, 2019
8:35p HAV » 6:42p ORD
Delta Air Lines 1 stop (22h07m)
$438
outward: Jan 2, 2019
7:00p ORD » 4:20p HAV
Delta Air Lines 2 stops (21h20m)
inbound: Jan 12, 2019
8:35p HAV » 6:42p ORD
Delta Air Lines 1 stop (22h07m)
$439
outward: Jan 2, 2019
3:10p ORD » 4:20p HAV
Delta Air Lines 2 stops (25h10m)
inbound: Jan 12, 2019
8:35p HAV » 6:42p ORD
Delta Air Lines 1 stop (22h07m)
$443
outward: Jan 3, 2019
4:10a ORD » 7:50p HAV
United Airlines 1 stop (15h40m)
inbound: Jan 12, 2019
8:50p HAV » 1:49p ORD
United Airlines 1 stop (16h59m)
$444
outward: Jan 2, 2019
8:45p ORD » 8:10p HAV
Aeromexico 2 stops (23h25m)
inbound: Jan 12, 2019
12:10p HAV » 6:59a ORD
Aeromexico 2 stops (18h49m)
$445
outward: Jan 2, 2019
8:40a ORD » 4:30a HAV
Aeromexico 2 stops (19h50m)
inbound: Jan 12, 2019
12:10p HAV » 6:59a ORD
Aeromexico 2 stops (18h49m)
$445
outward: Jan 2, 2019
8:40a ORD » 8:10p HAV
Aeromexico 2 stops (11h30m)
inbound: Jan 12, 2019
12:10p HAV » 6:59a ORD
Aeromexico 2 stops (18h49m)
$445
outward: Jan 2, 2019
8:40a ORD » 8:10p HAV
Aeromexico 2 stops (11h30m)
inbound: Jan 12, 2019
12:10p HAV » 6:59a ORD
Aeromexico 2 stops (18h49m)
$445
outward: Jan 2, 2019
1:00p ORD » 7:50p HAV
United Airlines 1 stop (6h50m)
inbound: Jan 12, 2019
8:50p HAV » 1:49p ORD
United Airlines 1 stop (16h59m)
$446
outward: Jan 2, 2019
8:45p ORD » 4:30a HAV
Aeromexico 2 stops (31h45m)
inbound: Jan 12, 2019
12:10p HAV » 6:59a ORD
Aeromexico 2 stops (18h49m)
$451
outward: Jan 3, 2019
4:10a ORD » 7:50p HAV
United Airlines 1 stop (15h40m)
inbound: Jan 12, 2019
8:50p HAV » 1:49p ORD
United Airlines 1 stop (16h59m)
Return
Departure
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

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Travel tips for flights Chicago - Havana

Average flight duration: 14h07m (flight with stopovers)

  • Arrival city:
  • Havana, Cuba
  • Airport(s):
  • José Martí International Airport (HAV)
  • Playa Baracoa Airport (UPB)
  • Local time:
  • Jul 16, 2018 6:50 AM, GMT-4
  • Weather:
  • min. 74ºF, max. 88ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jul 16, 2018 5:50 AM, GMT-5
  • Weather:
  • min. 66ºF, max. 77ºF