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

Find cheap airline tickets from Chicago to Havana by date

  • any
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • any
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • price
  • month of departure
  • month of return
$249
outward: Jan 15, 2019
11:00p ORD » 2:15p HAV
American Airlines 2 stops (15h15m)
inbound: Jan 24, 2019
3:10a HAV » 4:08p ORD
American Airlines 1 stop (12h58m)
$312
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Apr 1, 2019
9:15p HAV » 7:59a ORD
Aeromexico 1 stop (10h44m)
$315
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Apr 1, 2019
9:15p HAV » 7:59a ORD
Aeromexico 1 stop (10h44m)
$315
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Apr 1, 2019
9:15p HAV » 7:59a ORD
Aeromexico 1 stop (10h44m)
$316
outward: Mar 25, 2019
6:20a ORD » 8:05p HAV
Aeromexico 1 stop (13h45m)
inbound: Apr 1, 2019
9:15p HAV » 7:59a ORD
Aeromexico 1 stop (10h44m)
$327
outward: Mar 25, 2019
8:25p ORD » 4:25p HAV
Copa Airlines 1 stop (20h)
inbound: Mar 31, 2019
9:10p HAV » 10:21a ORD
Copa Airlines 1 stop (13h11m)
$327
outward: Mar 25, 2019
8:25p ORD » 4:25p HAV
Copa Airlines 1 stop (20h)
inbound: Mar 31, 2019
9:10p HAV » 10:21a ORD
Copa Airlines 1 stop (13h11m)
$327
outward: Mar 25, 2019
8:25p ORD » 4:25p HAV
Copa Airlines 1 stop (20h)
inbound: Mar 31, 2019
9:10p HAV » 10:30a ORD
Copa Airlines 1 stop (13h20m)
$328
outward: Mar 25, 2019
8:25p ORD » 4:25p HAV
Copa Airlines 1 stop (20h)
inbound: Mar 31, 2019
9:10p HAV » 10:30a ORD
Copa Airlines 1 stop (13h20m)
$328
outward: Mar 25, 2019
8:25p ORD » 4:25p HAV
Copa Airlines 1 stop (20h)
inbound: Mar 31, 2019
9:10p HAV » 10:30a ORD
Copa Airlines 1 stop (13h20m)
$329
outward: Mar 25, 2019
8:25p ORD » 4:25p HAV
Copa Airlines 1 stop (20h)
inbound: Mar 31, 2019
9:10p HAV » 10:30a ORD
Copa Airlines 1 stop (13h20m)
$330
outward: Mar 25, 2019
8:25p ORD » 4:25p HAV
Copa Airlines 1 stop (20h)
inbound: Mar 31, 2019
9:10p HAV » 10:30a ORD
Copa Airlines 1 stop (13h20m)
$341
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Mar 31, 2019
9:15p HAV » 7:59a ORD
Aeromexico 1 stop (10h44m)
$344
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Mar 31, 2019
9:15p HAV » 7:59a ORD
Aeromexico 1 stop (10h44m)
$344
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Mar 31, 2019
9:15p HAV » 7:59a ORD
Aeromexico 1 stop (10h44m)
$344
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Mar 31, 2019
9:15p HAV » 7:59a ORD
Aeromexico 1 stop (10h44m)
$351
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Mar 31, 2019
9:15p HAV » 7:59a ORD
Aeromexico 1 stop (10h44m)
$352
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Mar 31, 2019
12:10p HAV » 6:59a ORD
Aeromexico 2 stops (18h49m)
$352
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Mar 31, 2019
12:10p HAV » 6:59a ORD
Aeromexico 2 stops (18h49m)
$352
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Mar 31, 2019
12:10p HAV » 6:59a ORD
Aeromexico 2 stops (18h49m)
$352
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Mar 31, 2019
12:10p HAV » 6:59a ORD
Aeromexico 2 stops (18h49m)
$352
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Mar 31, 2019
12:10p HAV » 6:59a ORD
Aeromexico 2 stops (18h49m)
$352
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Mar 31, 2019
12:10p HAV » 6:59a ORD
Aeromexico 2 stops (18h49m)
$352
outward: Mar 25, 2019
7:35a ORD » 7:20p HAV
Aeromexico 1 stop (11h45m)
inbound: Mar 31, 2019
12:10p HAV » 6:59a ORD
Aeromexico 2 stops (18h49m)
$414
outward: Mar 25, 2019
6:20a ORD » 8:05p HAV
Aeromexico 1 stop (13h45m)
inbound: Apr 1, 2019
12:10p HAV » 9:35p ORD
Aeromexico 1 stop (9h25m)
$414
outward: Mar 25, 2019
6:20a ORD » 8:05p HAV
Aeromexico 1 stop (13h45m)
inbound: Apr 1, 2019
12:10p HAV » 9:35p ORD
Aeromexico 1 stop (9h25m)
$414
outward: Mar 25, 2019
6:20a ORD » 8:05p HAV
Aeromexico 1 stop (13h45m)
inbound: Apr 1, 2019
12:10p HAV » 9:35p ORD
Aeromexico 1 stop (9h25m)
$414
outward: Mar 25, 2019
6:20a ORD » 8:05p HAV
Aeromexico 1 stop (13h45m)
inbound: Apr 1, 2019
12:10p HAV » 9:35p ORD
Aeromexico 1 stop (9h25m)
$414
outward: Mar 25, 2019
6:20a ORD » 8:05p HAV
Aeromexico 1 stop (13h45m)
inbound: Apr 1, 2019
12:10p HAV » 9:35p ORD
Aeromexico 1 stop (9h25m)
$420
outward: Mar 25, 2019
8:28p ORD » 4:25p HAV
Copa Airlines 1 stop (19h57m)
inbound: Mar 31, 2019
6:05p HAV » 8:07p ORD
Copa Airlines 1 stop (26h02m)
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: Las Vegas - Havana New York - Havana London - Havana Miami - Havana See more routes

Airlines operating flights from Chicago to Havana

  • any
  • September 2018
  • October 2018
  • November 2018
  • December 2018
  • January 2019
  • February 2019
  • March 2019
  • April 2019
  • May 2019
  • June 2019
  • July 2019
  • August 2019
  • all
  • Aeromexico
  • American Airlines
  • JetBlue
  • United Airlines
JetBlue
outbound: Jan 15, 2019
JetBlue 1 stop
return: Jan 23, 2019
JetBlue 1 stop
American Airlines
outbound: Jan 15, 2019
American Airlines 1 stop
return: Jan 23, 2019
American Airlines 1 stop
Aeromexico
outbound: Jan 15, 2019
Aeromexico 1 stop
return: Jan 23, 2019
Aeromexico 2 stops
United Airlines
outbound: Jan 15, 2019
United Airlines 1 stop
return: Jan 23, 2019
United Airlines 1 stop

Travel tips for flights Chicago - Havana

Average flight duration: 16h35m (flight with stopovers)

  • Arrival city:
  • Havana, Cuba
  • Airport(s):
  • José Martí International Airport (HAV)
  • Playa Baracoa Airport (UPB)
  • Local time:
  • Sep 20, 2018 1:19 AM, GMT-4
  • Weather:
  • min. 75ºF, max. 85ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Sep 20, 2018 12:19 AM, GMT-5
  • Weather:
  • min. 63ºF, max. 77ºF