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

Find cheap airline tickets from Chicago to Cancun by date

  • any
  • February 2023
  • March 2023
  • April 2023
  • May 2023
  • June 2023
  • July 2023
  • August 2023
  • September 2023
  • October 2023
  • November 2023
  • December 2023
  • January 2024
  • any
  • February 2023
  • March 2023
  • April 2023
  • May 2023
  • June 2023
  • July 2023
  • August 2023
  • September 2023
  • October 2023
  • November 2023
  • December 2023
  • January 2024
  • price
  • month of departure
  • month of return
$254
Spirit Airlines outward: Feb 9, 2023
1:45a ORD » 11:58p CUN
Spirit Airlines 1 stop (22h13m)
Frontier Airlines inbound: Feb 13, 2023
10:30p CUN » 8:54p MDW
Frontier Airlines 1 stop (22h24m)
$296
Delta Air Lines outward: Apr 8, 2023
12:42p ORD » 2:45a CUN
Delta Air Lines 1 stop (14h03m)
Frontier Airlines inbound: Apr 13, 2023
7:02p CUN » 4:06p ORD
Frontier Airlines 1 stop (21h04m)
$298
Volaris outward: Sep 2, 2023
1:14a MDW » 5:41p CUN
Volaris 2 stops (16h27m)
Volaris inbound: Sep 6, 2023
2:14a CUN » 11:37a ORD
Volaris 1 stop (9h23m)
$307
Delta Air Lines outward: Apr 8, 2023
2:18a ORD » 7:55p CUN
Delta Air Lines 1 stop (17h37m)
Delta Air Lines inbound: Apr 12, 2023
11:30p CUN » 5:29a MDW
Delta Air Lines 1 stop (5h59m)
$309
VivaAerobús outward: Feb 26, 2023
7:35a ORD » 11:10p CUN
VivaAerobús 1 stop (15h35m)
VivaAerobús inbound: Mar 5, 2023
5:40p CUN » 9:30p ORD
VivaAerobús 1 stop (27h50m)
$312
Delta Air Lines outward: Apr 8, 2023
12:42p ORD » 2:45a CUN
Delta Air Lines 1 stop (14h03m)
Delta Air Lines inbound: Apr 12, 2023
11:30p CUN » 5:29a MDW
Delta Air Lines 1 stop (5h59m)
$312
Spirit Airlines outward: Feb 26, 2023
1:20p ORD » 11:58p CUN
Spirit Airlines 1 stop (10h38m)
VivaAerobús inbound: Mar 5, 2023
5:40p CUN » 9:30p ORD
VivaAerobús 1 stop (27h50m)
$312
Spirit Airlines outward: Feb 26, 2023
1:20p ORD » 11:58p CUN
Spirit Airlines 1 stop (10h38m)
VivaAerobús inbound: Mar 5, 2023
5:40p CUN » 9:30p ORD
VivaAerobús 1 stop (27h50m)
$313
Volaris outward: Sep 2, 2023
1:14a MDW » 3:16a CUN
Volaris 1 stop (26h02m)
Volaris inbound: Sep 5, 2023
8:18p CUN » 4:19a MDW
Volaris 1 stop (8h01m)
$326
Frontier Airlines outward: Apr 9, 2023
5:28p ORD » 9:35p CUN
Frontier Airlines direct (4h07m)
Frontier Airlines inbound: Apr 13, 2023
7:02p CUN » 8:20a MDW
Frontier Airlines 1 stop (13h18m)
$340
Aeromexico outward: Jun 28, 2023
10:59p ORD » 8:04a CUN
Aeromexico 1 stop (9h05m)
Aeromexico inbound: Jul 4, 2023
5:08p CUN » 4:44a ORD
Aeromexico 1 stop (11h36m)
$342
Frontier Airlines outward: Feb 10, 2023
4:15a ORD » 6:03p CUN
Frontier Airlines 1 stop (13h48m)
Frontier Airlines inbound: Feb 12, 2023
10:30p CUN » 2:03p ORD
Frontier Airlines 1 stop (15h33m)
$348
VivaAerobús outward: May 26, 2023
6:55a ORD » 4:10a CUN
VivaAerobús 1 stop (21h15m)
Aeromexico inbound: May 30, 2023
8:29p CUN » 4:44a ORD
Aeromexico 1 stop (8h15m)
$350
Spirit Airlines outward: Feb 24, 2023
2:56a ORD » 3:21p CUN
Spirit Airlines 1 stop (12h25m)
VivaAerobús inbound: Feb 26, 2023
5:40p CUN » 9:30p ORD
VivaAerobús 1 stop (27h50m)
$353
Aeromexico outward: Jun 26, 2023
10:59p ORD » 8:04a CUN
Aeromexico 1 stop (9h05m)
Aeromexico inbound: Jun 30, 2023
5:08p CUN » 4:44a ORD
Aeromexico 1 stop (11h36m)
$355
VivaAerobús outward: May 26, 2023
6:55a ORD » 9:50p CUN
VivaAerobús 1 stop (14h55m)
VivaAerobús inbound: May 30, 2023
5:55a CUN » 5:40a ORD
VivaAerobús 1 stop (23h45m)
$364
Aeromexico outward: Apr 4, 2023
10:59p ORD » 8:04a CUN
Aeromexico 1 stop (9h05m)
VivaAerobús inbound: Apr 7, 2023
11:40p CUN » 5:05p ORD
VivaAerobús 1 stop (17h25m)
$371
Volaris outward: Sep 1, 2023
7:11a ORD » 9:20p CUN
Volaris 1 stop (14h09m)
VivaAerobús inbound: Sep 5, 2023
7:45p CUN » 9:25p ORD
VivaAerobús 1 stop (25h40m)
$371
Volaris outward: Sep 1, 2023
1:27p ORD » 10:26p CUN
Volaris 1 stop (8h59m)
Aeromexico inbound: Sep 5, 2023
11:32p CUN » 9:09p ORD
Aeromexico 1 stop (21h37m)
$373
VivaAerobús outward: May 27, 2023
6:55a ORD » 8:00a CUN
VivaAerobús 1 stop (25h05m)
Aeromexico inbound: May 30, 2023
10:29p CUN » 6:49a ORD
Aeromexico 1 stop (8h20m)
$374
VivaAerobús outward: Apr 4, 2023
6:55a ORD » 8:00a CUN
VivaAerobús 1 stop (25h05m)
VivaAerobús inbound: Apr 7, 2023
11:40p CUN » 5:05p ORD
VivaAerobús 1 stop (17h25m)
$378
Volaris outward: May 26, 2023
6:04p ORD » 10:02p CUN
Volaris direct (3h58m)
Volaris inbound: May 29, 2023
8:00p CUN » 11:58p ORD
Volaris direct (3h58m)
$382
Aeromexico outward: Apr 10, 2023
2:00p ORD » 5:25a CUN
Aeromexico 1 stop (15h25m)
VivaAerobús inbound: Apr 14, 2023
5:50p CUN » 5:40a ORD
VivaAerobús 1 stop (11h50m)
$385
VivaAerobús outward: Mar 23, 2023
6:55a ORD » 5:10a CUN
VivaAerobús 1 stop (22h15m)
Spirit Airlines inbound: Mar 28, 2023
5:25p CUN » 7:47a ORD
Spirit Airlines 1 stop (14h22m)
$446
American Airlines outward: Mar 14, 2023
2:59a ORD » 7:35p CUN
American Airlines 1 stop (16h36m)
Volaris inbound: Mar 18, 2023
4:01p CUN » 3:19a MDW
Volaris 1 stop (11h18m)
$503
Frontier Airlines outward: Apr 6, 2023
1:24a ORD » 6:17p CUN
Frontier Airlines 1 stop (16h53m)
Unknown Company inbound: Apr 10, 2023
12:00a CUN » 1:41a ORD
Unknown Company 1 stop (25h41m)
$536
Frontier Airlines outward: Apr 7, 2023
1:24a ORD » 6:26p CUN
Frontier Airlines 1 stop (17h02m)
Unknown Company inbound: Apr 10, 2023
12:00a CUN » 2:23p ORD
Unknown Company 1 stop (14h23m)
$1,160
Air Canada outward: Feb 10, 2023
8:00p ORD » 3:40a CUN
Air Canada 1 stop (7h40m)
Air Canada inbound: Feb 13, 2023
4:10p CUN » 1:50a ORD
Air Canada 1 stop (9h40m)
Return
Departure
Choose when you'd like to depart to Cancun (Mexico):
Find the cheapest Chicago Cancun flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Chicago - Cancun with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from Chicago to Cancun

  • any
  • February 2023
  • March 2023
  • April 2023
  • May 2023
  • June 2023
  • July 2023
  • August 2023
  • September 2023
  • October 2023
  • November 2023
  • December 2023
  • January 2024
  • all
  • Aeromexico
  • Delta Air Lines
  • United Airlines
Aeromexico
outbound: May 26, 2023
Aeromexico 1 stop
return: May 30, 2023
Aeromexico 1 stop
Delta Air Lines
outbound: Feb 26, 2023
Delta Air Lines 1 stop
return: Mar 5, 2023
Aeromexico 1 stop
United Airlines
outbound: Mar 23, 2023
United Airlines 1 stop
return: Mar 28, 2023
United Airlines 1 stop

Travel tips for flights Chicago - Cancun

Average flight duration: 4h07m (direct flight)

  • Arrival city:
  • Cancun, Mexico
  • Airport(s):
  • Cancún International Airport (CUN)
  • Local time:
  • Feb 5, 2023 1:12 PM, GMT-5
  • Weather:
  • min. 69ºF, max. 80ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Chicago Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Feb 5, 2023 12:12 PM, GMT-6
  • Weather:
  • min. 27ºF, max. 42ºF