Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline VivaAerobus

The cheapest airline(s) flying from Chicago to Cancun is VivaAerobus.

  • VivaAerobus VivaAerobus
  • United Airlines United Airlines
  • Frontier Airlines Frontier Airlines
  • Spirit Airlines Spirit Airlines
  • American Airlines American Airlines
  • Volaris Volaris
  • JetBlue Airways JetBlue Airways
  • Southwest Airlines Southwest Airlines
  • Aeromexico Aeromexico
  • Air Canada Air Canada
Cheapest Month January

Travel Period: December 2024 - November 2025

The cheapest month(s) to fly from Chicago to Cancun is January.

  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
Cheapest Day of the Week Saturday

The cheapest day(s) of the week to fly from Chicago to Cancun is Saturday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Sat, 2 Nov, 2024

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    • Airline Filter by Airline
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      • Availability
        • M
        • T
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        • T
        • F
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        • S
      • 06:00 ORD
        10:46 CUN
        3Hrs, 46m Direct
      • ORDChicago O'Hare International Airport 06:00 - CUN 10:46 3h 46m Direct
      • ORDChicago O'Hare International Airport 06:00
      • CUNCancun Airport 10:46
      • 3h 46m
      • Direct
      • Spirit Airlines (NK 104)Airbus Industrie A321 Sharklets
      • Spirit Airlines (NK 104)
        • M
        • -
        • W
        • -
        • F
        • S
        • -
      • Airbus Industrie A321 Sharklets
      • 07:10 MDW
        12:00 CUN
        3Hrs, 50m Direct
      • MDWChicago Midway Airport 07:10 - CUN 12:00 3h 50m Direct
      • MDWChicago Midway Airport 07:10
      • CUNCancun Airport 12:00
      • 3h 50m
      • Direct
      • Southwest Airlines (WN 228)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 228)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 07:13 ORD
        12:09 CUN
        3Hrs, 56m Direct
      • ORDChicago O'Hare International Airport 07:13 - CUN 12:09 3h 56m Direct
      • ORDChicago O'Hare International Airport 07:13
      • CUNCancun Airport 12:09
      • 3h 56m
      • Direct
      • Frontier Airlines (F9 44)Airbus A320 Neo
      • Frontier Airlines (F9 44)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Airbus A320 Neo
      • 08:42 ORD
        13:33 CUN
        3Hrs, 51m Direct
      • ORDChicago O'Hare International Airport 08:42 - CUN 13:33 3h 51m Direct
      • ORDChicago O'Hare International Airport 08:42
      • CUNCancun Airport 13:33
      • 3h 51m
      • Direct
      • United Airlines (UA 1656)Boeing 777
      • United Airlines (UA 1656)
        • M
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        • T
        • F
        • S
        • S
      • Boeing 777
      • 08:53 ORD
        13:38 CUN
        3Hrs, 45m Direct
      • ORDChicago O'Hare International Airport 08:53 - CUN 13:38 3h 45m Direct
      • ORDChicago O'Hare International Airport 08:53
      • CUNCancun Airport 13:38
      • 3h 45m
      • Direct
      • American Airlines (AA 1503)Boeing 737 800
      • American Airlines (AA 1503)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 09:13 ORD
        14:10 CUN
        3Hrs, 57m Direct
      • ORDChicago O'Hare International Airport 09:13 - CUN 14:10 3h 57m Direct
      • ORDChicago O'Hare International Airport 09:13
      • CUNCancun Airport 14:10
      • 3h 57m
      • Direct
      • United Airlines (UA 1198)Boeing 737 Max 9 Passenger
      • United Airlines (UA 1198)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 Max 9 Passenger
      • 09:25 MDW
        14:15 CUN
        3Hrs, 50m Direct
      • MDWChicago Midway Airport 09:25 - CUN 14:15 3h 50m Direct
      • MDWChicago Midway Airport 09:25
      • CUNCancun Airport 14:15
      • 3h 50m
      • Direct
      • Southwest Airlines (WN 220)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 220)
        • M
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        • W
        • -
        • F
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 10:00 ORD
        14:50 CUN
        3Hrs, 50m Direct
      • ORDChicago O'Hare International Airport 10:00 - CUN 14:50 3h 50m Direct
      • ORDChicago O'Hare International Airport 10:00
      • CUNCancun Airport 14:50
      • 3h 50m
      • Direct
      • American Airlines (AA 492)Boeing 737 800
      • American Airlines (AA 492)
        • M
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        • W
        • -
        • F
        • S
        • S
      • Boeing 737 800
      • 10:25 ORD
        15:20 CUN
        3Hrs, 55m Direct
      • ORDChicago O'Hare International Airport 10:25 - CUN 15:20 3h 55m Direct
      • ORDChicago O'Hare International Airport 10:25
      • CUNCancun Airport 15:20
      • 3h 55m
      • Direct
      • Southwest Airlines (WN 1510)Boeing 737 700
      • Southwest Airlines (WN 1510)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 700
      • 11:40 MDW
        16:25 CUN
        3Hrs, 45m Direct
      • MDWChicago Midway Airport 11:40 - CUN 16:25 3h 45m Direct
      • MDWChicago Midway Airport 11:40
      • CUNCancun Airport 16:25
      • 3h 45m
      • Direct
      • Southwest Airlines (WN 228)Boeing 737 700
      • Southwest Airlines (WN 228)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • Boeing 737 700
      • 15:00 MDW
        19:45 CUN
        3Hrs, 45m Direct
      • MDWChicago Midway Airport 15:00 - CUN 19:45 3h 45m Direct
      • MDWChicago Midway Airport 15:00
      • CUNCancun Airport 19:45
      • 3h 45m
      • Direct
      • Southwest Airlines (WN 218)Boeing 737 700
      • Southwest Airlines (WN 218)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • Boeing 737 700
      • 01:15 ORD
        10:20 CUN
        8Hrs, 05m 1 Stop (MTY)
      • ORDChicago O'Hare International Airport 01:15 - CUN 10:20 8h 05m 1 Stop (MTY) Monterrey
      • ORDChicago O'Hare International Airport 01:15
        MTYMonterrey General Mariano Escobedo Airport 06:50
      • MTYMonterrey General Mariano Escobedo Airport 04:55
        CUNCancun Airport 10:20
      • 8h 05m (1h 55m)
      • 1 Stop MTY · Monterrey 1h 55m
      • VivaAerobus (VB 635)Airbus
        VivaAerobus (VB 2163)Airbus
      • VivaAerobus (VB 635)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 01:15 ORD
        10:20 CUN
        8Hrs, 05m 1 Stop (MTY)
      • ORDChicago O'Hare International Airport 01:15 - CUN 10:20 8h 05m 1 Stop (MTY) Monterrey
      • ORDChicago O'Hare International Airport 01:15
        MTYMonterrey General Mariano Escobedo Airport 06:50
      • MTYMonterrey General Mariano Escobedo Airport 04:55
        CUNCancun Airport 10:20
      • 8h 05m (1h 55m)
      • 1 Stop MTY · Monterrey 1h 55m
      • VivaAerobus (VB 635)Airbus
        VivaAerobus (VB 2163)Airbus
      • VivaAerobus (VB 635)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 03:45 ORD
        13:03 CUN
        8Hrs, 18m 1 Stop (QRO)
      • ORDChicago O'Hare International Airport 03:45 - CUN 13:03 8h 18m 1 Stop (QRO) Queretaro
      • ORDChicago O'Hare International Airport 03:45
        QROQueretaro Airport 09:46
      • QROQueretaro Airport 07:58
        CUNCancun Airport 13:03
      • 8h 18m (1h 48m)
      • 1 Stop QRO · Queretaro 1h 48m
      • Volaris (Y4 7891)Airbus
        Volaris (Y4 3517)Airbus
      • Volaris (Y4 7891)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 05:00 MDW
        11:55 CUN
        5Hrs, 55m 1 Stop (HOU)
      • MDWChicago Midway Airport 05:00 - CUN 11:55 5h 55m 1 Stop (HOU) Houston
      • MDWChicago Midway Airport 05:00
        HOUHouston Hobby Airport 08:40
      • HOUHouston Hobby Airport 07:50
        CUNCancun Airport 11:55
      • 5h 55m (50m)
      • 1 Stop HOU · Houston 50m
      • Southwest Airlines (WN 480)Boeing 737 700
        Southwest Airlines (WN 317)Boeing 737 700
      • Southwest Airlines (WN 480)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:00 ORD
        12:05 CUN
        6Hrs, 05m 1 Stop (FLL)
      • ORDChicago O'Hare International Airport 05:00 - CUN 12:05 6h 05m 1 Stop (FLL) Miami
      • ORDChicago O'Hare International Airport 05:00
        FLLFort Lauderdale/Hollywood Intl Airport 10:15
      • FLLFort Lauderdale/Hollywood Intl Airport 09:00
        CUNCancun Airport 12:05
      • 6h 05m (1h 15m)
      • 1 Stop FLL · Miami 1h 15m
      • Spirit Airlines (NK 19)Airbus Industrie A321 Sharklets
        Spirit Airlines (NK 527)Airbus Industrie A321 Sharklets
      • Spirit Airlines (NK 19)
        • M
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        • T
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        • S
      • 05:00 ORD
        12:15 CUN
        6Hrs, 15m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 05:00 - CUN 12:15 6h 15m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 05:00
        MIAMiami International Airport 10:10
      • MIAMiami International Airport 09:07
        CUNCancun Airport 12:15
      • 6h 15m (1h 03m)
      • 1 Stop MIA · Miami 1h 03m
      • American Airlines (AA 2984)Boeing 737 800
        American Airlines (AA 1157)Airbus A321 Neo
      • American Airlines (AA 2984)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 05:00 ORD
        12:15 CUN
        6Hrs, 15m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 05:00 - CUN 12:15 6h 15m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 05:00
        MIAMiami International Airport 10:10
      • MIAMiami International Airport 09:07
        CUNCancun Airport 12:15
      • 6h 15m (1h 03m)
      • 1 Stop MIA · Miami 1h 03m
      • American Airlines (AA 2984)Boeing 737 800
        American Airlines (AA 1157)Airbus
      • American Airlines (AA 2984)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:00 ORD
        12:20 CUN
        6Hrs, 20m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 05:00 - CUN 12:20 6h 20m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 08:30
      • DFWDallas/Fort Worth Intl Airport 07:41
        CUNCancun Airport 12:20
      • 6h 20m (49m)
      • 1 Stop DFW · Dallas 49m
      • American Airlines (AA 370)Boeing 737 800
        American Airlines (AA 1190)Boeing 737 800
      • American Airlines (AA 370)
        • M
        • T
        • W
        • T
        • -
        • S
        • S
      • 05:00 ORD
        12:30 CUN
        6Hrs, 30m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:00 - CUN 12:30 6h 30m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:00
        CLTCharlotte Airport 09:25
      • CLTCharlotte Airport 07:55
        CUNCancun Airport 12:30
      • 6h 30m (1h 30m)
      • 1 Stop CLT · Charlotte 1h 30m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 895)Airbus
      • American Airlines (AA 2842)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • 05:00 MDW
        13:05 CUN
        7Hrs, 05m 1 Stop (MCO)
      • MDWChicago Midway Airport 05:00 - CUN 13:05 7h 05m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 05:00
        MCOOrlando International Airport 10:50
      • MCOOrlando International Airport 08:45
        CUNCancun Airport 13:05
      • 7h 05m (2h 05m)
      • 1 Stop MCO · Orlando 2h 05m
      • Southwest Airlines (WN 1519)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 318)Boeing 737 700
      • Southwest Airlines (WN 1519)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:00 ORD
        13:05 CUN
        7Hrs, 05m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 05:00 - CUN 13:05 7h 05m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 09:30
      • DFWDallas/Fort Worth Intl Airport 07:41
        CUNCancun Airport 13:05
      • 7h 05m (1h 49m)
      • 1 Stop DFW · Dallas 1h 49m
      • American Airlines (AA 370)Boeing 737 800
        American Airlines (AA 1001)Boeing 787 9
      • American Airlines (AA 370)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • 05:00 ORD
        13:12 CUN
        7Hrs, 12m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 05:00 - CUN 13:12 7h 12m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 05:00
        DFWDallas/Fort Worth Intl Airport 09:30
      • DFWDallas/Fort Worth Intl Airport 07:41
        CUNCancun Airport 13:12
      • 7h 12m (1h 49m)
      • 1 Stop DFW · Dallas 1h 49m
      • American Airlines (AA 370)Boeing 737 800
        American Airlines (AA 1001)Airbus
      • American Airlines (AA 370)
        • M
        • T
        • W
        • T
        • -
        • -
        • -
      • 05:00 MDW
        13:15 CUN
        7Hrs, 15m 1 Stop (MCO)
      • MDWChicago Midway Airport 05:00 - CUN 13:15 7h 15m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 05:00
        MCOOrlando International Airport 11:00
      • MCOOrlando International Airport 08:45
        CUNCancun Airport 13:15
      • 7h 15m (2h 15m)
      • 1 Stop MCO · Orlando 2h 15m
      • Southwest Airlines (WN 2538)Boeing 737 800
        Southwest Airlines (WN 318)Boeing 737 700
      • Southwest Airlines (WN 2538)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:00 ORD
        13:30 CUN
        7Hrs, 30m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:00 - CUN 13:30 7h 30m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:00
        CLTCharlotte Airport 10:30
      • CLTCharlotte Airport 07:55
        CUNCancun Airport 13:30
      • 7h 30m (2h 35m)
      • 1 Stop CLT · Charlotte 2h 35m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 1265)Airbus
      • American Airlines (AA 2842)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:00 MDW
        14:00 CUN
        8Hrs, 00m 1 Stop (HOU)
      • MDWChicago Midway Airport 05:00 - CUN 14:00 8h 1 Stop (HOU) Houston
      • MDWChicago Midway Airport 05:00
        HOUHouston Hobby Airport 10:45
      • HOUHouston Hobby Airport 07:50
        CUNCancun Airport 14:00
      • 8h (2h 55m)
      • 1 Stop HOU · Houston 2h 55m
      • Southwest Airlines (WN 480)Boeing 737 700
        Southwest Airlines (WN 305)Boeing 737 700
      • Southwest Airlines (WN 480)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:00 ORD
        14:00 CUN
        8Hrs, 00m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 05:00 - CUN 14:00 8h 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 05:00
        MIAMiami International Airport 12:05
      • MIAMiami International Airport 09:07
        CUNCancun Airport 14:00
      • 8h (2h 58m)
      • 1 Stop MIA · Miami 2h 58m
      • American Airlines (AA 2984)Boeing 737 800
        American Airlines (AA 2422)Boeing 737 800
      • American Airlines (AA 2984)
        • M
        • T
        • W
        • -
        • F
        • S
        • S
      • 05:00 ORD
        14:30 CUN
        8Hrs, 30m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:00 - CUN 14:30 8h 30m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:00
        CLTCharlotte Airport 11:25
      • CLTCharlotte Airport 07:55
        CUNCancun Airport 14:30
      • 8h 30m (3h 30m)
      • 1 Stop CLT · Charlotte 3h 30m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 886)Airbus
      • American Airlines (AA 2842)
        • M
        • T
        • W
        • -
        • F
        • -
        • S
      • 05:00 ORD
        14:36 CUN
        8Hrs, 36m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:00 - CUN 14:36 8h 36m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:00
        CLTCharlotte Airport 11:16
      • CLTCharlotte Airport 07:55
        CUNCancun Airport 14:36
      • 8h 36m (3h 21m)
      • 1 Stop CLT · Charlotte 3h 21m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 886)Airbus
      • American Airlines (AA 2842)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 05:01 ORD
        14:03 CUN
        8Hrs, 02m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 05:01 - CUN 14:03 8h 02m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 05:01
        DENDenver Intl Airport 07:52
      • DENDenver Intl Airport 06:57
        CUNCancun Airport 14:03
      • 8h 02m (55m)
      • 1 Stop DEN · Denver 55m
      • Frontier Airlines (F9 3173)Airbus A320 Neo
        Frontier Airlines (F9 70)Airbus A321 Neo
      • Frontier Airlines (F9 3173)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:10 MDW
        13:05 CUN
        6Hrs, 55m 1 Stop (MCO)
      • MDWChicago Midway Airport 05:10 - CUN 13:05 6h 55m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 05:10
        MCOOrlando International Airport 10:50
      • MCOOrlando International Airport 08:55
        CUNCancun Airport 13:05
      • 6h 55m (1h 55m)
      • 1 Stop MCO · Orlando 1h 55m
      • Southwest Airlines (WN 2538)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 318)Boeing 737 700
      • Southwest Airlines (WN 2538)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:10 MDW
        14:44 CUN
        8Hrs, 34m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:10 - CUN 14:44 8h 34m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:10
        DENDenver Intl Airport 08:33
      • DENDenver Intl Airport 06:59
        CUNCancun Airport 14:44
      • 8h 34m (1h 34m)
      • 1 Stop DEN · Denver 1h 34m
      • Frontier Airlines (F9 2209)Airbus A320 Neo
        Frontier Airlines (F9 70)Airbus A321 Neo
      • Frontier Airlines (F9 2209)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:15 MDW
        13:25 CUN
        7Hrs, 10m 1 Stop (BNA)
      • MDWChicago Midway Airport 05:15 - CUN 13:25 7h 10m 1 Stop (BNA) Nashville
      • MDWChicago Midway Airport 05:15
        BNANashville Airport 09:20
      • BNANashville Airport 06:45
        CUNCancun Airport 13:25
      • 7h 10m (2h 35m)
      • 1 Stop BNA · Nashville 2h 35m
      • Southwest Airlines (WN 2665)Boeing 737 700
        Southwest Airlines (WN 386)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2665)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:15 MDW
        13:50 CUN
        7Hrs, 35m 1 Stop (BNA)
      • MDWChicago Midway Airport 05:15 - CUN 13:50 7h 35m 1 Stop (BNA) Nashville
      • MDWChicago Midway Airport 05:15
        BNANashville Airport 09:45
      • BNANashville Airport 06:45
        CUNCancun Airport 13:50
      • 7h 35m (3h)
      • 1 Stop BNA · Nashville 3h
      • Southwest Airlines (WN 2665)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 386)Boeing 737 700
      • Southwest Airlines (WN 2665)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:20 MDW
        14:55 CUN
        8Hrs, 35m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:20 - CUN 14:55 8h 35m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:20
        DENDenver Intl Airport 08:55
      • DENDenver Intl Airport 07:05
        CUNCancun Airport 14:55
      • 8h 35m (1h 50m)
      • 1 Stop DEN · Denver 1h 50m
      • Southwest Airlines (WN 2248)Boeing 737 700
        Southwest Airlines (WN 601)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2248)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:25 MDW
        13:30 CUN
        7Hrs, 05m 1 Stop (BWI)
      • MDWChicago Midway Airport 05:25 - CUN 13:30 7h 05m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 05:25
        BWIBaltimore Washington International Airport 09:35
      • BWIBaltimore Washington International Airport 08:15
        CUNCancun Airport 13:30
      • 7h 05m (1h 20m)
      • 1 Stop BWI · Baltimore 1h 20m
      • Southwest Airlines (WN 281)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1609)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 281)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:30 MDW
        13:10 CUN
        6Hrs, 40m 1 Stop (MCO)
      • MDWChicago Midway Airport 05:30 - CUN 13:10 6h 40m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 05:30
        MCOOrlando International Airport 10:55
      • MCOOrlando International Airport 09:15
        CUNCancun Airport 13:10
      • 6h 40m (1h 40m)
      • 1 Stop MCO · Orlando 1h 40m
      • Southwest Airlines (WN 2538)Boeing 737 800
        Southwest Airlines (WN 318)Boeing 737 700
      • Southwest Airlines (WN 2538)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:30 MDW
        13:50 CUN
        7Hrs, 20m 1 Stop (BWI)
      • MDWChicago Midway Airport 05:30 - CUN 13:50 7h 20m 1 Stop (BWI) Baltimore
      • MDWChicago Midway Airport 05:30
        BWIBaltimore Washington International Airport 09:55
      • BWIBaltimore Washington International Airport 08:20
        CUNCancun Airport 13:50
      • 7h 20m (1h 35m)
      • 1 Stop BWI · Baltimore 1h 35m
      • Southwest Airlines (WN 281)Boeing 737 800
        Southwest Airlines (WN 1609)Boeing 737 700
      • Southwest Airlines (WN 281)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:30 MDW
        14:00 CUN
        7Hrs, 30m 1 Stop (BNA)
      • MDWChicago Midway Airport 05:30 - CUN 14:00 7h 30m 1 Stop (BNA) Nashville
      • MDWChicago Midway Airport 05:30
        BNANashville Airport 09:50
      • BNANashville Airport 07:00
        CUNCancun Airport 14:00
      • 7h 30m (2h 50m)
      • 1 Stop BNA · Nashville 2h 50m
      • Southwest Airlines (WN 2861)Boeing 737 700
        Southwest Airlines (WN 386)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2861)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:35 MDW
        12:45 CUN
        6Hrs, 10m 1 Stop (STL)
      • MDWChicago Midway Airport 05:35 - CUN 12:45 6h 10m 1 Stop (STL) Saint Louis
      • MDWChicago Midway Airport 05:35
        STLSt Louis Lambert Intl Airport 08:25
      • STLSt Louis Lambert Intl Airport 06:55
        CUNCancun Airport 12:45
      • 6h 10m (1h 30m)
      • 1 Stop STL · Saint Louis 1h 30m
      • Southwest Airlines (WN 4837)Boeing 737 800
        Southwest Airlines (WN 1985)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 4837)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 05:45 ORD
        12:54 CUN
        6Hrs, 09m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 05:45 - CUN 12:54 6h 09m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 05:45
        IAHHouston George Bush Intercontinental Airport 09:31
      • IAHHouston George Bush Intercontinental Airport 08:42
        CUNCancun Airport 12:54
      • 6h 09m (49m)
      • 1 Stop IAH · Houston 49m
      • United Airlines (UA 2850)Boeing 737 900
        United Airlines (UA 1018)Boeing 737 900
      • United Airlines (UA 2850)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 05:45 MDW
        12:55 CUN
        6Hrs, 10m 1 Stop (HOU)
      • MDWChicago Midway Airport 05:45 - CUN 12:55 6h 10m 1 Stop (HOU) Houston
      • MDWChicago Midway Airport 05:45
        HOUHouston Hobby Airport 09:40
      • HOUHouston Hobby Airport 08:35
        CUNCancun Airport 12:55
      • 6h 10m (1h 05m)
      • 1 Stop HOU · Houston 1h 05m
      • Southwest Airlines (WN 1149)Boeing 737 800
        Southwest Airlines (WN 325)Boeing 737 700
      • Southwest Airlines (WN 1149)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:45 ORD
        13:05 CUN
        6Hrs, 20m 1 Stop (MCO)
      • ORDChicago O'Hare International Airport 05:45 - CUN 13:05 6h 20m 1 Stop (MCO) Orlando
      • ORDChicago O'Hare International Airport 05:45
        MCOOrlando International Airport 10:50
      • MCOOrlando International Airport 09:30
        CUNCancun Airport 13:05
      • 6h 20m (1h 20m)
      • 1 Stop MCO · Orlando 1h 20m
      • Southwest Airlines (WN 425)Boeing 737 700
        Southwest Airlines (WN 318)Boeing 737 700
      • Southwest Airlines (WN 425)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:45 ORD
        13:30 CUN
        6Hrs, 45m 1 Stop (BWI)
      • ORDChicago O'Hare International Airport 05:45 - CUN 13:30 6h 45m 1 Stop (BWI) Baltimore
      • ORDChicago O'Hare International Airport 05:45
        BWIBaltimore Washington International Airport 09:35
      • BWIBaltimore Washington International Airport 08:40
        CUNCancun Airport 13:30
      • 6h 45m (55m)
      • 1 Stop BWI · Baltimore 55m
      • Southwest Airlines (WN 1266)Boeing 737 800
        Southwest Airlines (WN 1609)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1266)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 05:45 ORD
        13:30 CUN
        6Hrs, 45m 1 Stop (BWI)
      • ORDChicago O'Hare International Airport 05:45 - CUN 13:30 6h 45m 1 Stop (BWI) Baltimore
      • ORDChicago O'Hare International Airport 05:45
        BWIBaltimore Washington International Airport 09:35
      • BWIBaltimore Washington International Airport 08:40
        CUNCancun Airport 13:30
      • 6h 45m (55m)
      • 1 Stop BWI · Baltimore 55m
      • Southwest Airlines (WN 1467)Boeing 737 800
        Southwest Airlines (WN 1609)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1467)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:45 ORD
        13:34 CUN
        6Hrs, 49m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 05:45 - CUN 13:34 6h 49m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 05:45
        IAHHouston George Bush Intercontinental Airport 10:10
      • IAHHouston George Bush Intercontinental Airport 08:42
        CUNCancun Airport 13:34
      • 6h 49m (1h 28m)
      • 1 Stop IAH · Houston 1h 28m
      • United Airlines (UA 2850)Boeing 737 900
        United Airlines (UA 1014)Boeing 737 Max 9 Passenger
      • United Airlines (UA 2850)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 05:45 MDW
        14:00 CUN
        7Hrs, 15m 1 Stop (HOU)
      • MDWChicago Midway Airport 05:45 - CUN 14:00 7h 15m 1 Stop (HOU) Houston
      • MDWChicago Midway Airport 05:45
        HOUHouston Hobby Airport 10:45
      • HOUHouston Hobby Airport 08:35
        CUNCancun Airport 14:00
      • 7h 15m (2h 10m)
      • 1 Stop HOU · Houston 2h 10m
      • Southwest Airlines (WN 1149)Boeing 737 800
        Southwest Airlines (WN 305)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1149)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:45 MDW
        14:20 CUN
        7Hrs, 35m 1 Stop (DEN)
      • MDWChicago Midway Airport 05:45 - CUN 14:20 7h 35m 1 Stop (DEN) Denver
      • MDWChicago Midway Airport 05:45
        DENDenver Intl Airport 08:20
      • DENDenver Intl Airport 07:30
        CUNCancun Airport 14:20
      • 7h 35m (50m)
      • 1 Stop DEN · Denver 50m
      • Southwest Airlines (WN 2248)Boeing 737 800
        Southwest Airlines (WN 601)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2248)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:45 ORD
        15:08 CUN
        8Hrs, 23m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 05:45 - CUN 15:08 8h 23m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 05:45
        IAHHouston George Bush Intercontinental Airport 11:44
      • IAHHouston George Bush Intercontinental Airport 08:42
        CUNCancun Airport 15:08
      • 8h 23m (3h 02m)
      • 1 Stop IAH · Houston 3h 02m
      • United Airlines (UA 2850)Boeing 737 900
        United Airlines (UA 1014)Boeing 737 900
      • United Airlines (UA 2850)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:50 MDW
        12:45 CUN
        5Hrs, 55m 1 Stop (HOU)
      • MDWChicago Midway Airport 05:50 - CUN 12:45 5h 55m 1 Stop (HOU) Houston
      • MDWChicago Midway Airport 05:50
        HOUHouston Hobby Airport 09:30
      • HOUHouston Hobby Airport 08:40
        CUNCancun Airport 12:45
      • 5h 55m (50m)
      • 1 Stop HOU · Houston 50m
      • Southwest Airlines (WN 2694)Boeing 737 700
        Southwest Airlines (WN 325)Boeing 737 700
      • Southwest Airlines (WN 2694)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:50 MDW
        15:25 CUN
        8Hrs, 35m 1 Stop (HOU)
      • MDWChicago Midway Airport 05:50 - CUN 15:25 8h 35m 1 Stop (HOU) Houston
      • MDWChicago Midway Airport 05:50
        HOUHouston Hobby Airport 12:10
      • HOUHouston Hobby Airport 08:40
        CUNCancun Airport 15:25
      • 8h 35m (3h 30m)
      • 1 Stop HOU · Houston 3h 30m
      • Southwest Airlines (WN 2694)Boeing 737 700
        Southwest Airlines (WN 305)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 2694)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:00 MDW
        13:05 CUN
        6Hrs, 05m 1 Stop (MCO)
      • MDWChicago Midway Airport 06:00 - CUN 13:05 6h 05m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 06:00
        MCOOrlando International Airport 10:50
      • MCOOrlando International Airport 09:45
        CUNCancun Airport 13:05
      • 6h 05m (1h 05m)
      • 1 Stop MCO · Orlando 1h 05m
      • Southwest Airlines (WN 1601)Boeing 737 800
        Southwest Airlines (WN 318)Boeing 737 700
      • Southwest Airlines (WN 1601)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 06:00 ORD
        13:05 CUN
        6Hrs, 05m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 06:00 - CUN 13:05 6h 05m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 06:00
        DFWDallas/Fort Worth Intl Airport 09:30
      • DFWDallas/Fort Worth Intl Airport 08:42
        CUNCancun Airport 13:05
      • 6h 05m (48m)
      • 1 Stop DFW · Dallas 48m
      • American Airlines (AA 482)Airbus
        American Airlines (AA 1001)Boeing 787 9
      • American Airlines (AA 482)
        • -
        • -
        • -
        • -
        • -
        • S
        • S
      • 06:00 ORD
        13:12 CUN
        6Hrs, 12m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 06:00 - CUN 13:12 6h 12m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 06:00
        DFWDallas/Fort Worth Intl Airport 09:30
      • DFWDallas/Fort Worth Intl Airport 08:42
        CUNCancun Airport 13:12
      • 6h 12m (48m)
      • 1 Stop DFW · Dallas 48m
      • American Airlines (AA 482)Airbus
        American Airlines (AA 1001)Airbus
      • American Airlines (AA 482)
        • M
        • T
        • W
        • T
        • F
        • -
        • -
      • 06:00 ORD
        14:20 CUN
        7Hrs, 20m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 06:00 - CUN 14:20 7h 20m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 06:00
        DFWDallas/Fort Worth Intl Airport 10:20
      • DFWDallas/Fort Worth Intl Airport 08:42
        CUNCancun Airport 14:20
      • 7h 20m (1h 38m)
      • 1 Stop DFW · Dallas 1h 38m
      • American Airlines (AA 482)Airbus
        American Airlines (AA 2874)Airbus
      • American Airlines (AA 482)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 06:00 ORD
        14:40 CUN
        7Hrs, 40m 1 Stop (PHL)
      • ORDChicago O'Hare International Airport 06:00 - CUN 14:40 7h 40m 1 Stop (PHL) Philadelphia
      • ORDChicago O'Hare International Airport 06:00
        PHLPhiladelphia International Airport 10:35
      • PHLPhiladelphia International Airport 08:51
        CUNCancun Airport 14:40
      • 7h 40m (1h 44m)
      • 1 Stop PHL · Philadelphia 1h 44m
      • American Airlines (AA 1854)Airbus
        American Airlines (AA 805)Airbus
      • American Airlines (AA 1854)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:00 ORD
        14:44 CUN
        7Hrs, 44m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 06:00 - CUN 14:44 7h 44m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 06:00
        DENDenver Intl Airport 08:33
      • DENDenver Intl Airport 07:45
        CUNCancun Airport 14:44
      • 7h 44m (48m)
      • 1 Stop DEN · Denver 48m
      • Frontier Airlines (F9 3173)Airbus A320 Neo
        Frontier Airlines (F9 70)Airbus A321 Neo
      • Frontier Airlines (F9 3173)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 06:00 ORD
        15:05 CUN
        8Hrs, 05m 1 Stop (DEN)
      • ORDChicago O'Hare International Airport 06:00 - CUN 15:05 8h 05m 1 Stop (DEN) Denver
      • ORDChicago O'Hare International Airport 06:00
        DENDenver Intl Airport 08:54
      • DENDenver Intl Airport 07:45
        CUNCancun Airport 15:05
      • 8h 05m (1h 09m)
      • 1 Stop DEN · Denver 1h 09m
      • Frontier Airlines (F9 3173)Airbus A320 Neo
        Frontier Airlines (F9 70)Airbus A321 Neo
      • Frontier Airlines (F9 3173)
        • -
        • -
        • W
        • -
        • F
        • -
        • -
      • 06:00 ORD
        15:08 CUN
        8Hrs, 08m 1 Stop (BOS)
      • ORDChicago O'Hare International Airport 06:00 - CUN 15:08 8h 08m 1 Stop (BOS) Boston
      • ORDChicago O'Hare International Airport 06:00
        BOSBoston Logan International Airport 10:20
      • BOSBoston Logan International Airport 09:17
        CUNCancun Airport 15:08
      • 8h 08m (1h 03m)
      • 1 Stop BOS · Boston 1h 03m
      • JetBlue Airways (B6 1012)Airbus A220 300
        JetBlue Airways (B6 671)Airbus
      • JetBlue Airways (B6 1012)
        • M
        • T
        • W
        • -
        • -
        • S
        • S
      • 06:05 MDW
        13:50 CUN
        6Hrs, 45m 1 Stop (MCI)
      • MDWChicago Midway Airport 06:05 - CUN 13:50 6h 45m 1 Stop (MCI) Kansas City
      • MDWChicago Midway Airport 06:05
        MCIKansas City International Airport 09:25
      • MCIKansas City International Airport 07:40
        CUNCancun Airport 13:50
      • 6h 45m (1h 45m)
      • 1 Stop MCI · Kansas City 1h 45m
      • Southwest Airlines (WN 176)Boeing 737 700
        Southwest Airlines (WN 751)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 176)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:05 MDW
        14:15 CUN
        7Hrs, 10m 1 Stop (MCI)
      • MDWChicago Midway Airport 06:05 - CUN 14:15 7h 10m 1 Stop (MCI) Kansas City
      • MDWChicago Midway Airport 06:05
        MCIKansas City International Airport 09:55
      • MCIKansas City International Airport 07:40
        CUNCancun Airport 14:15
      • 7h 10m (2h 15m)
      • 1 Stop MCI · Kansas City 2h 15m
      • Southwest Airlines (WN 4695)Boeing 737 800
        Southwest Airlines (WN 751)Boeing 737 700
      • Southwest Airlines (WN 4695)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
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      What’s the fastest flight time from Chicago to Cancun?

      The fastest flight time for direct flights from Chicago to Cancun is 3 hours 45 minutes. Check latest flight schedules & prices on Wego.

      What’s the most popular airline flying from Chicago to Cancun?

      The most popular airline flying from Chicago to Cancun is American Airlines. Find the latest flight deals on Wego.

      How far is Cancun from Chicago?

      The flight distance between Chicago and Cancun is 2305km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 01:15. The last flight of the day departs at 01:15. See the full list of flight times on Wego.

      How many airlines offer direct flights from Chicago to Cancun?

      There are 5 airlines that offer direct flights from Chicago to Cancun. Find out the list of airlines on Wego.

      All Airports in Cancun

      Cancun Airport CUN

      Popular Airlines flying from Chicago to Cancun

      American Airlines ‏()
      Spirit Airlines ‏()
      United Airlines ‏()

      Popular Destinations from Cancun

      Popular Destinations from Chicago

      Popular Hotels in Cancun

      Hotels In Popular Destinations