1. Home
  2. Flights Search
  3. Flights from Chicago to Cancun

Cheap flights from Chicago to Cancun

Find cheap Cancun to Chicago flights with our free search service. Compare all available fares for direct or connection flights from Cancun to Chicago.

Round-trip
  • One-way
  • Round-trip
1 adult
Adults 12 years or over
1
Children 2-11 years
0
Infants 0-23 months
0
Cancel Done
Economy Class
  • Economy Class
  • Business Class
Done
Done

Chicago to Cancun flight schedules

Flight Departure Date Arrival Date Price Duration Number of stops Updated
Chicago (CHI) - Cancun (CUN) 2026-12-16 2026-12-30 294 USD 35 hours 38 minutes Connection 2026-09-29T01:18:23
Chicago (CHI) - Cancun (CUN) 2026-11-15 2026-11-22 453 USD 13 hours 15 minutes Connection 2026-09-28T23:34:06
Chicago (CHI) - Cancun (CUN) 2026-11-01 2026-11-05 529 USD 12 hours 45 minutes Connection 2026-09-24T13:53:15
Chicago (CHI) - Cancun (CUN) 2026-10-13 2026-10-19 587 USD 14 hours 9 minutes Connection 2026-09-23T09:58:34
Chicago (CHI) - Cancun (CUN) 2027-05-19 2027-05-24 587 USD 17 hours 20 minutes Connection 2026-09-28T14:02:09
Chicago (CHI) - Cancun (CUN) 2026-12-21 2026-12-25 591 USD 9 hours 10 minutes Connection 2026-09-26T08:22:01
Chicago (CHI) - Cancun (CUN) 2026-12-22 2026-12-25 591 USD 17 hours 10 minutes Connection 2026-09-26T08:22:01
Chicago (CHI) - Cancun (CUN) 2026-10-12 2026-10-16 595 USD 15 hours 24 minutes Connection 2026-09-27T03:38:30
Chicago (CHI) - Cancun (CUN) 2026-12-20 2026-12-25 626 USD 19 hours 30 minutes Connection 2026-09-26T08:22:01
Chicago (CHI) - Cancun (CUN) 2026-12-21 2026-12-26 628 USD 16 hours 23 minutes Connection 2026-09-26T08:22:01
Chicago (CHI) - Cancun (CUN) 2026-12-22 2026-12-26 628 USD 24 hours 23 minutes Connection 2026-09-26T08:22:01
Chicago (CHI) - Cancun (CUN) 2027-04-12 2027-04-17 640 USD 7 hours 20 minutes Direct 2026-09-25T14:30:24
Chicago (CHI) - Cancun (CUN) 2026-10-13 2026-10-17 650 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-10-13 2026-10-18 650 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-12-20 2026-12-26 663 USD 26 hours 43 minutes Connection 2026-09-26T08:22:01
Chicago (CHI) - Cancun (CUN) 2026-12-20 2026-12-27 687 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-12-20 2026-12-28 687 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-12-20 2026-12-29 687 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-12-20 2026-12-30 687 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-12-20 2026-12-31 687 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-12-20 2027-01-01 687 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-12-20 2027-01-02 687 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-12-20 2027-01-03 687 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-12-20 2027-01-04 687 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-12-20 2027-01-05 687 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-12-20 2027-01-06 687 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-12-20 2027-01-07 687 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-12-20 2027-01-08 687 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-12-20 2027-01-09 687 USD 0 minutes Direct 2026-09-29T00:00:00
Chicago (CHI) - Cancun (CUN) 2026-11-20 2026-11-23 699 USD 26 hours 55 minutes Connection 2026-09-27T16:39:43

Chicago to Cancun flight status

Flight Origin Destination Departure Arrival Equip
WN216 Chicago (MDW) Cancun (CUN) 10:05 a.m. 1:40 p.m. B737
WN228 Chicago (MDW) Cancun (CUN) 6:25 a.m. 10 a.m. B737
WN218 Chicago (MDW) Cancun (CUN) 10:30 a.m. 2 p.m. B737
US2995 Chicago (MDW) Cancun (CUN) 10 p.m. 11:55 p.m. CRJ
C55166 Chicago (MDW) Cancun (CUN) 12:25 p.m. 5:10 p.m.

Popular Flights Searchs

  • Domestic Destinations
  • International Destinations