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

Find cheap airline tickets from Chicago to Cancun by date

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  • July 2018
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  • December 2018
  • January 2019
  • February 2019
  • March 2019
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  • May 2019
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  • any
  • July 2018
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  • January 2019
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  • June 2019
  • price
  • month of departure
  • month of return
$259
outward: Sep 12, 2018
7:25a ORD » 2:02a CUN
Aeromexico 1 stop (18h37m)
inbound: Sep 16, 2018
7:30p CUN » 2:17a ORD
Spirit Airlines direct (6h47m)
Verify
26 days ago
$260
outward: Nov 10, 2018
2:00p ORD » 6:30p CUN
Spirit Airlines direct (4h30m)
inbound: Nov 18, 2018
5:45p CUN » 12:10p ORD
Aeromexico 1 stop (18h25m)
Verify
26 days ago
$423
outward: Jan 1, 2019
3:56p ORD » 8:45p CUN
United Airlines direct (4h49m)
inbound: Jan 6, 2019
2:15a CUN » 5:30p ORD
Unknown Company 1 stop (15h15m)
Verify
25 days ago
$442
outward: Dec 23, 2018
3:21a ORD » 5:19p CUN
Volaris 1 stop (13h58m)
inbound: Dec 27, 2018
8:39p CUN » 11:29p ORD
United Airlines direct (2h50m)
Verify
24 days ago
$453
outward: Dec 23, 2018
3:21a ORD » 5:19p CUN
Volaris 1 stop (13h58m)
inbound: Dec 27, 2018
8:39p CUN » 11:29p ORD
United Airlines direct (2h50m)
Verify
22 days ago
$453
outward: Dec 23, 2018
3:21a ORD » 5:19p CUN
Volaris 1 stop (13h58m)
inbound: Dec 27, 2018
8:39p CUN » 11:29p ORD
United Airlines direct (2h50m)
Verify
21 days ago
$455
outward: Dec 23, 2018
3:21a ORD » 5:19p CUN
Volaris 1 stop (13h58m)
inbound: Dec 27, 2018
8:39p CUN » 11:29p ORD
United Airlines direct (2h50m)
Verify
25 days ago
$1,403
outward: Jan 1, 2019
3:50p ORD » 2:34a CUN
Delta Air Lines 1 stop (10h44m)
inbound: Jan 4, 2019
7:15p CUN » 12:24a MDW
Delta Air Lines 1 stop (5h09m)
Verify
25 days ago
$1,403
outward: Jan 1, 2019
3:50p ORD » 2:34a CUN
Delta Air Lines 1 stop (10h44m)
inbound: Jan 6, 2019
11:15p CUN » 4:25a MDW
Delta Air Lines 1 stop (5h10m)
Verify
25 days ago
$1,403
outward: Dec 31, 2018
7:10p MDW » 2:34a CUN
Delta Air Lines 1 stop (7h24m)
inbound: Jan 4, 2019
7:15p CUN » 12:24a MDW
Delta Air Lines 1 stop (5h09m)
Verify
25 days ago
$1,403
outward: Dec 31, 2018
7:10p MDW » 2:34a CUN
Delta Air Lines 1 stop (7h24m)
inbound: Jan 5, 2019
7:15p CUN » 12:20a MDW
Delta Air Lines 1 stop (5h05m)
Verify
25 days ago
$1,403
outward: Dec 31, 2018
7:10p MDW » 2:34a CUN
Delta Air Lines 1 stop (7h24m)
inbound: Jan 6, 2019
11:15p CUN » 4:25a MDW
Delta Air Lines 1 stop (5h10m)
Verify
25 days ago
$1,479
outward: Jan 2, 2019
2:05p ORD » 8:45p CUN
Delta Air Lines 1 stop (6h40m)
inbound: Jan 4, 2019
7:15p CUN » 12:24a MDW
Delta Air Lines 1 stop (5h09m)
Verify
25 days ago
$1,479
outward: Jan 2, 2019
2:05p ORD » 8:45p CUN
Delta Air Lines 1 stop (6h40m)
inbound: Jan 5, 2019
7:15p CUN » 12:20a MDW
Delta Air Lines 1 stop (5h05m)
Verify
25 days ago
$1,479
outward: Jan 2, 2019
2:05p ORD » 8:45p CUN
Delta Air Lines 1 stop (6h40m)
inbound: Jan 6, 2019
11:15p CUN » 4:25a MDW
Delta Air Lines 1 stop (5h10m)
Verify
25 days ago
Return
Departure
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28 December Dec Friday $outDate.dayShortName
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$1,402 $1,402 $1,402
01 January Jan Tuesday $outDate.dayShortName
$1,402 $422
02 January Jan Wednesday $outDate.dayShortName
$1,479 $1,479 $1,479
03 January Jan Thursday $outDate.dayShortName
Availability of fares is not guaranteed for offers found in the last 7 days.
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: Las Vegas - Cancun New York - Cancun London - Cancun Miami - Cancun San Francisco - Cancun See more routes

Airlines operating flights from Chicago to Cancun

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

Travel tips for flights Chicago - Cancun

Average flight duration: 4h49m (direct flight)

  • Arrival city:
  • Cancun, Mexico
  • Airport(s):
  • Cancún International Airport (CUN)
  • Local time:
  • Jul 22, 2018 2:12 AM, GMT-5
  • Weather:
  • min. 72ºF, max. 90ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jul 22, 2018 2:12 AM, GMT-5
  • Weather:
  • min. 67ºF, max. 75ºF