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

Find cheap airline tickets from Chicago to Cancun by date

  • any
  • September 2023
  • October 2023
  • November 2023
  • December 2023
  • January 2024
  • February 2024
  • March 2024
  • April 2024
  • May 2024
  • June 2024
  • July 2024
  • August 2024
  • any
  • September 2023
  • October 2023
  • November 2023
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  • January 2024
  • February 2024
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  • May 2024
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  • August 2024
  • price
  • month of departure
  • month of return
$189
Frontier Airlines outward: Dec 8, 2023
7:41p MDW » 11:29p CUN
Frontier Airlines direct (3h48m)
Frontier Airlines inbound: Dec 12, 2023
12:50a CUN » 4:35a MDW
Frontier Airlines direct (3h45m)
$206
Frontier Airlines outward: Dec 8, 2023
7:41p MDW » 11:29p CUN
Frontier Airlines direct (3h48m)
Frontier Airlines inbound: Dec 12, 2023
12:50a CUN » 4:35a MDW
Frontier Airlines direct (3h45m)
$222
Frontier Airlines outward: Dec 10, 2023
7:41p MDW » 11:29p CUN
Frontier Airlines direct (3h48m)
Frontier Airlines inbound: Dec 18, 2023
12:13a CUN » 3:00p ORD
Frontier Airlines 1 stop (14h47m)
$223
Frontier Airlines outward: Dec 10, 2023
7:41p MDW » 11:29p CUN
Frontier Airlines direct (3h48m)
Frontier Airlines inbound: Dec 18, 2023
12:07a CUN » 2:29p ORD
Frontier Airlines 1 stop (14h22m)
$226
Frontier Airlines outward: Dec 10, 2023
7:41p MDW » 11:29p CUN
Frontier Airlines direct (3h48m)
Frontier Airlines inbound: Dec 18, 2023
12:07a CUN » 2:29p ORD
Frontier Airlines 1 stop (14h22m)
$226
Frontier Airlines outward: Dec 10, 2023
7:41p MDW » 11:29p CUN
Frontier Airlines direct (3h48m)
Frontier Airlines inbound: Dec 18, 2023
12:07a CUN » 2:29p ORD
Frontier Airlines 1 stop (14h22m)
$227
Spirit Airlines outward: Oct 27, 2023
1:10p ORD » 4:54p CUN
Spirit Airlines direct (3h44m)
Spirit Airlines inbound: Oct 31, 2023
11:01p CUN » 3:12a ORD
Spirit Airlines direct (4h11m)
$227
Spirit Airlines outward: Oct 27, 2023
1:10p ORD » 4:54p CUN
Spirit Airlines direct (3h44m)
Spirit Airlines inbound: Oct 31, 2023
11:01p CUN » 3:12a ORD
Spirit Airlines direct (4h11m)
$227
Spirit Airlines outward: Oct 27, 2023
1:10p ORD » 4:54p CUN
Spirit Airlines direct (3h44m)
Spirit Airlines inbound: Oct 31, 2023
11:01p CUN » 3:12a ORD
Spirit Airlines direct (4h11m)
$228
Frontier Airlines outward: Dec 8, 2023
3:58p MDW » 7:10p CUN
Frontier Airlines 1 stop (27h12m)
Frontier Airlines inbound: Dec 12, 2023
12:50a CUN » 4:35a MDW
Frontier Airlines direct (3h45m)
$228
Frontier Airlines outward: Dec 8, 2023
3:58p MDW » 7:10p CUN
Frontier Airlines 1 stop (27h12m)
Frontier Airlines inbound: Dec 12, 2023
12:50a CUN » 4:35a MDW
Frontier Airlines direct (3h45m)
$234
Frontier Airlines outward: Dec 10, 2023
7:41p MDW » 11:29p CUN
Frontier Airlines direct (3h48m)
Frontier Airlines inbound: Dec 17, 2023
6:52p CUN » 2:53p MDW
Frontier Airlines 1 stop (20h01m)
$244
Spirit Airlines outward: Oct 6, 2023
3:05a ORD » 2:59p CUN
Spirit Airlines 1 stop (11h54m)
Spirit Airlines inbound: Oct 8, 2023
5:49p CUN » 9:55p ORD
Spirit Airlines direct (4h06m)
$258
Frontier Airlines outward: Dec 8, 2023
3:58p MDW » 7:10p CUN
Frontier Airlines 1 stop (27h12m)
Frontier Airlines inbound: Dec 12, 2023
12:11a CUN » 3:00p ORD
Frontier Airlines 1 stop (14h49m)
$297
Frontier Airlines outward: Dec 7, 2023
3:58p MDW » 7:10p CUN
Frontier Airlines 1 stop (27h12m)
Frontier Airlines inbound: Dec 10, 2023
11:01p CUN » 7:38a MDW
Frontier Airlines 1 stop (8h37m)
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
  • September 2023
  • October 2023
  • November 2023
  • December 2023
  • January 2024
  • February 2024
  • March 2024
  • April 2024
  • May 2024
  • June 2024
  • July 2024
  • August 2024
  • all
  • Aeromexico
  • American Airlines
  • Frontier Airlines
  • Spirit Airlines
  • United Airlines
Spirit Airlines
outbound: Oct 27, 2023
Spirit Airlines direct
return: Oct 31, 2023
Spirit Airlines direct
Frontier Airlines
outbound: Dec 8, 2023
Frontier Airlines direct
return: Dec 11, 2023
Frontier Airlines direct
American Airlines
outbound: Dec 7, 2023
American Airlines 1 stop
return: Dec 10, 2023
Frontier Airlines 1 stop
United Airlines
outbound: Oct 27, 2023
United Airlines direct
return: Oct 31, 2023
United Airlines direct
Aeromexico
outbound: Oct 5, 2023
Aeromexico 1 stop
return: Oct 8, 2023
American Airlines direct

Travel tips for flights Chicago - Cancun

Average flight duration: 3h48m (direct flight)

  • Arrival city:
  • Cancun, Mexico
  • Airport(s):
  • Cancún International Airport (CUN)
  • Local time:
  • Sep 28, 2023 10:30 AM, GMT-5
  • Weather:
  • min. 78ºF, max. 87ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Chicago Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Sep 28, 2023 10:30 AM, GMT-5
  • Weather:
  • min. 63ºF, max. 70ºF