Flight Schedules

Last Updated: Mon, 2 Sep, 2024

  • Time Earliest
    • Earliest
    • Latest
  • Depart Earliest
    • Earliest
    • Latest
  • Arrive
    • Earliest
    • Latest
  • duration
    • Shortest
    • Longest
  • Stopover
    All
    • Airline Filter by Airline
      View All Airline
      • Availability
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 10:35 CUN
        14:50 ORD
        4Hrs, 15m Direct
      • CUNCancun Airport 10:35 - ORD 14:50 4h 15m Direct
      • CUNCancun Airport 10:35
      • ORDChicago O'Hare International Airport 14:50
      • 4h 15m
      • Direct
      • Spirit Airlines (NK 105)Airbus Industrie A321 Sharklets
      • Spirit Airlines (NK 105)
        • M
        • -
        • W
        • -
        • F
        • S
        • -
      • Airbus Industrie A321 Sharklets
      • 10:51 CUN
        14:52 ORD
        4Hrs, 01m Direct
      • CUNCancun Airport 10:51 - ORD 14:52 4h 01m Direct
      • CUNCancun Airport 10:51
      • ORDChicago O'Hare International Airport 14:52
      • 4h 01m
      • Direct
      • Frontier Airlines (F9 45)Airbus A320 Neo
      • Frontier Airlines (F9 45)
        • -
        • T
        • -
        • T
        • -
        • S
        • -
      • Airbus A320 Neo
      • 11:01 CUN
        15:01 ORD
        4Hrs, 00m Direct
      • CUNCancun Airport 11:01 - ORD 15:01 4h Direct
      • CUNCancun Airport 11:01
      • ORDChicago O'Hare International Airport 15:01
      • 4h
      • Direct
      • Frontier Airlines (F9 45)Airbus A321 Neo
      • Frontier Airlines (F9 45)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • Airbus A321 Neo
      • 12:05 CUN
        16:14 ORD
        4Hrs, 09m Direct
      • CUNCancun Airport 12:05 - ORD 16:14 4h 09m Direct
      • CUNCancun Airport 12:05
      • ORDChicago O'Hare International Airport 16:14
      • 4h 09m
      • Direct
      • Frontier Airlines (F9 45)Airbus A320 Neo
      • Frontier Airlines (F9 45)
        • M
        • -
        • -
        • -
        • F
        • -
        • S
      • Airbus A320 Neo
      • 12:20 CUN
        16:15 ORD
        3Hrs, 55m Direct
      • CUNCancun Airport 12:20 - ORD 16:15 3h 55m Direct
      • CUNCancun Airport 12:20
      • ORDChicago O'Hare International Airport 16:15
      • 3h 55m
      • Direct
      • United Airlines (UA 1196)Boeing 737 900
      • United Airlines (UA 1196)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 900
      • 14:25 CUN
        18:05 MDW
        3Hrs, 40m Direct
      • CUNCancun Airport 14:25 - MDW 18:05 3h 40m Direct
      • CUNCancun Airport 14:25
      • MDWChicago Midway Airport 18:05
      • 3h 40m
      • Direct
      • Southwest Airlines (WN 217)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 217)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 Max 8 Passenger
      • 14:35 CUN
        18:15 MDW
        3Hrs, 40m Direct
      • CUNCancun Airport 14:35 - MDW 18:15 3h 40m Direct
      • CUNCancun Airport 14:35
      • MDWChicago Midway Airport 18:15
      • 3h 40m
      • Direct
      • Southwest Airlines (WN 217)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 217)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • Boeing 737 Max 8 Passenger
      • 14:44 CUN
        18:45 ORD
        4Hrs, 01m Direct
      • CUNCancun Airport 14:44 - ORD 18:45 4h 01m Direct
      • CUNCancun Airport 14:44
      • ORDChicago O'Hare International Airport 18:45
      • 4h 01m
      • Direct
      • American Airlines (AA 215)Boeing 737 800
      • American Airlines (AA 215)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • Boeing 737 800
      • 15:10 CUN
        18:45 MDW
        3Hrs, 35m Direct
      • CUNCancun Airport 15:10 - MDW 18:45 3h 35m Direct
      • CUNCancun Airport 15:10
      • MDWChicago Midway Airport 18:45
      • 3h 35m
      • Direct
      • Southwest Airlines (WN 217)Boeing 737 700
      • Southwest Airlines (WN 217)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • Boeing 737 700
      • 15:38 CUN
        19:33 ORD
        3Hrs, 55m Direct
      • CUNCancun Airport 15:38 - ORD 19:33 3h 55m Direct
      • CUNCancun Airport 15:38
      • ORDChicago O'Hare International Airport 19:33
      • 3h 55m
      • Direct
      • United Airlines (UA 1667)Boeing 737 900
      • United Airlines (UA 1667)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 900
      • 15:50 CUN
        19:25 MDW
        3Hrs, 35m Direct
      • CUNCancun Airport 15:50 - MDW 19:25 3h 35m Direct
      • CUNCancun Airport 15:50
      • MDWChicago Midway Airport 19:25
      • 3h 35m
      • Direct
      • Southwest Airlines (WN 217)Boeing 737 700
      • Southwest Airlines (WN 217)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • Boeing 737 700
      • 19:00 CUN
        03:11 ORD
        8Hrs, 11m 1 Stop (GDL)
      • CUNCancun Airport 19:00 - ORD 03:11 8h 11m 1 Stop (GDL) Guadalajara
      • CUNCancun Airport 19:00
        GDLGuadalajara Airport 22:07
      • GDLGuadalajara Airport 20:49
        ORDChicago O'Hare International Airport 03:11
      • 8h 11m (1h 18m)
      • 1 Stop GDL · Guadalajara 1h 18m
      • Volaris (Y4 1045)Airbus
        Volaris (Y4 1704)Airbus A320 Neo
      • Volaris (Y4 1045)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 06:00 CUN
        14:13 ORD
        8Hrs, 13m 1 Stop (MEX)
      • CUNCancun Airport 06:00 - ORD 14:13 8h 13m 1 Stop (MEX) Mexico City
      • CUNCancun Airport 06:00
        MEXMexico City Juarez International Airport 08:45
      • MEXMexico City Juarez International Airport 07:25
        ORDChicago O'Hare International Airport 14:13
      • 8h 13m (1h 20m)
      • 1 Stop MEX · Mexico City 1h 20m
      • Aeromexico (AM 501)Boeing 737 Max 9 Passenger
        Aeromexico (AM 686)Boeing 737 Max 8 Passenger
      • Aeromexico (AM 501)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 07:05 CUN
        15:20 ORD
        8Hrs, 15m 1 Stop (MTY)
      • CUNCancun Airport 07:05 - ORD 15:20 8h 15m 1 Stop (MTY) Monterrey
      • CUNCancun Airport 07:05
        MTYMonterrey General Mariano Escobedo Airport 10:50
      • MTYMonterrey General Mariano Escobedo Airport 08:30
        ORDChicago O'Hare International Airport 15:20
      • 8h 15m (2h 20m)
      • 1 Stop MTY · Monterrey 2h 20m
      • VivaAerobus (VB 2196)Airbus
        VivaAerobus (VB 632)Airbus
      • VivaAerobus (VB 2196)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:05 CUN
        15:20 ORD
        8Hrs, 15m 1 Stop (MTY)
      • CUNCancun Airport 07:05 - ORD 15:20 8h 15m 1 Stop (MTY) Monterrey
      • CUNCancun Airport 07:05
        MTYMonterrey General Mariano Escobedo Airport 10:50
      • MTYMonterrey General Mariano Escobedo Airport 08:30
        ORDChicago O'Hare International Airport 15:20
      • 8h 15m (2h 20m)
      • 1 Stop MTY · Monterrey 2h 20m
      • VivaAerobus (VB 2196)Airbus
        VivaAerobus (VB 632)Airbus
      • VivaAerobus (VB 2196)
        • M
        • -
        • W
        • -
        • F
        • -
        • -
      • 07:51 CUN
        14:54 ORD
        7Hrs, 03m 1 Stop (IAH)
      • CUNCancun Airport 07:51 - ORD 14:54 7h 03m 1 Stop (IAH) Houston
      • CUNCancun Airport 07:51
        IAHHouston George Bush Intercontinental Airport 12:08
      • IAHHouston George Bush Intercontinental Airport 10:19
        ORDChicago O'Hare International Airport 14:54
      • 7h 03m (1h 49m)
      • 1 Stop IAH · Houston 1h 49m
      • United Airlines (UA 1059)Boeing 737 900
        United Airlines (UA 1168)Boeing 757 300 Series
      • United Airlines (UA 1059)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 07:51 CUN
        14:55 ORD
        7Hrs, 04m 1 Stop (IAH)
      • CUNCancun Airport 07:51 - ORD 14:55 7h 04m 1 Stop (IAH) Houston
      • CUNCancun Airport 07:51
        IAHHouston George Bush Intercontinental Airport 12:08
      • IAHHouston George Bush Intercontinental Airport 10:19
        ORDChicago O'Hare International Airport 14:55
      • 7h 04m (1h 49m)
      • 1 Stop IAH · Houston 1h 49m
      • United Airlines (UA 1059)Boeing 737 900
        United Airlines (UA 1168)Boeing 737 900
      • United Airlines (UA 1059)
        • M
        • T
        • W
        • T
        • F
        • S
        • -
      • 08:00 CUN
        15:43 ORD
        7Hrs, 43m 1 Stop (DFW)
      • CUNCancun Airport 08:00 - ORD 15:43 7h 43m 1 Stop (DFW) Dallas
      • CUNCancun Airport 08:00
        DFWDallas/Fort Worth Intl Airport 13:20
      • DFWDallas/Fort Worth Intl Airport 10:59
        ORDChicago O'Hare International Airport 15:43
      • 7h 43m (2h 21m)
      • 1 Stop DFW · Dallas 2h 21m
      • American Airlines (AA 316)Boeing 737 800
        American Airlines (AA 2428)Airbus
      • American Airlines (AA 316)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 08:15 CUN
        14:31 ORD
        6Hrs, 16m 1 Stop (ATL)
      • CUNCancun Airport 08:15 - ORD 14:31 6h 16m 1 Stop (ATL) Atlanta
      • CUNCancun Airport 08:15
        ATLAtlanta Hartsfield-Jackson Intl Airport 13:30
      • ATLAtlanta Hartsfield-Jackson Intl Airport 11:51
        ORDChicago O'Hare International Airport 14:31
      • 6h 16m (1h 39m)
      • 1 Stop ATL · Atlanta 1h 39m
      • Delta Air Lines (DL 609)Boeing 737 800
        Delta Air Lines (DL 1477)Boeing 737 900
      • Delta Air Lines (DL 609)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 08:15 CUN
        14:59 MDW
        6Hrs, 44m 1 Stop (ATL)
      • CUNCancun Airport 08:15 - MDW 14:59 6h 44m 1 Stop (ATL) Atlanta
      • CUNCancun Airport 08:15
        ATLAtlanta Hartsfield-Jackson Intl Airport 14:07
      • ATLAtlanta Hartsfield-Jackson Intl Airport 11:51
        MDWChicago Midway Airport 14:59
      • 6h 44m (2h 16m)
      • 1 Stop ATL · Atlanta 2h 16m
      • Delta Air Lines (DL 609)Boeing 737 800
        Delta Air Lines (DL 1739)Boeing 717
      • Delta Air Lines (DL 609)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 08:15 CUN
        16:44 ORD
        8Hrs, 29m 1 Stop (ATL)
      • CUNCancun Airport 08:15 - ORD 16:44 8h 29m 1 Stop (ATL) Atlanta
      • CUNCancun Airport 08:15
        ATLAtlanta Hartsfield-Jackson Intl Airport 15:40
      • ATLAtlanta Hartsfield-Jackson Intl Airport 11:51
        ORDChicago O'Hare International Airport 16:44
      • 8h 29m (3h 49m)
      • 1 Stop ATL · Atlanta 3h 49m
      • Delta Air Lines (DL 609)Boeing 737 800
        Delta Air Lines (DL 2738)Boeing 737 900
      • Delta Air Lines (DL 609)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 08:15 CUN
        16:46 ORD
        8Hrs, 31m 1 Stop (ATL)
      • CUNCancun Airport 08:15 - ORD 16:46 8h 31m 1 Stop (ATL) Atlanta
      • CUNCancun Airport 08:15
        ATLAtlanta Hartsfield-Jackson Intl Airport 15:40
      • ATLAtlanta Hartsfield-Jackson Intl Airport 11:51
        ORDChicago O'Hare International Airport 16:46
      • 8h 31m (3h 49m)
      • 1 Stop ATL · Atlanta 3h 49m
      • Delta Air Lines (DL 609)Boeing 737 800
        Delta Air Lines (DL 2738)Airbus
      • Delta Air Lines (DL 609)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 08:45 CUN
        16:47 ORD
        8Hrs, 02m 1 Stop (EWR)
      • CUNCancun Airport 08:45 - ORD 16:47 8h 02m 1 Stop (EWR) New York City
      • CUNCancun Airport 08:45
        EWRNewark Liberty International Airport 15:15
      • EWRNewark Liberty International Airport 13:36
        ORDChicago O'Hare International Airport 16:47
      • 8h 02m (1h 39m)
      • 1 Stop EWR · New York City 1h 39m
      • United Airlines (UA 1988)Boeing 737 900
        United Airlines (UA 1144)Boeing 757 200 Series
      • United Airlines (UA 1988)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 10:25 CUN
        18:33 ORD
        8Hrs, 08m 1 Stop (YYZ)
      • CUNCancun Airport 10:25 - ORD 18:33 8h 08m 1 Stop (YYZ) Toronto
      • CUNCancun Airport 10:25
        YYZToronto Lester B Pearson Intl Airport 17:30
      • YYZToronto Lester B Pearson Intl Airport 15:25
        ORDChicago O'Hare International Airport 18:33
      • 8h 08m (2h 05m)
      • 1 Stop YYZ · Toronto 2h 05m
      • Air Canada (AC 1811)Airbus
        United Airlines (UA 213)Airbus
      • Air Canada (AC 1811)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 10:25 CUN
        18:33 ORD
        8Hrs, 08m 1 Stop (YYZ)
      • CUNCancun Airport 10:25 - ORD 18:33 8h 08m 1 Stop (YYZ) Toronto
      • CUNCancun Airport 10:25
        YYZToronto Lester B Pearson Intl Airport 17:30
      • YYZToronto Lester B Pearson Intl Airport 15:25
        ORDChicago O'Hare International Airport 18:33
      • 8h 08m (2h 05m)
      • 1 Stop YYZ · Toronto 2h 05m
      • Air Canada (AC 1811)Airbus
        United Airlines (UA 213)Airbus
      • Air Canada (AC 1811)
        • M
        • T
        • -
        • T
        • F
        • S
        • S
      • 10:35 CUN
        18:16 ORD
        7Hrs, 41m 1 Stop (MIA)
      • CUNCancun Airport 10:35 - ORD 18:16 7h 41m 1 Stop (MIA) Miami
      • CUNCancun Airport 10:35
        MIAMiami International Airport 15:55
      • MIAMiami International Airport 13:25
        ORDChicago O'Hare International Airport 18:16
      • 7h 41m (2h 30m)
      • 1 Stop MIA · Miami 2h 30m
      • American Airlines (AA 1469)Boeing 737 800
        American Airlines (AA 650)Boeing 737 800
      • American Airlines (AA 1469)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 10:35 CUN
        18:36 ORD
        8Hrs, 01m 1 Stop (MIA)
      • CUNCancun Airport 10:35 - ORD 18:36 8h 01m 1 Stop (MIA) Miami
      • CUNCancun Airport 10:35
        MIAMiami International Airport 16:15
      • MIAMiami International Airport 13:25
        ORDChicago O'Hare International Airport 18:36
      • 8h 01m (2h 50m)
      • 1 Stop MIA · Miami 2h 50m
      • American Airlines (AA 1469)Boeing 737 800
        American Airlines (AA 650)Boeing 737 800
      • American Airlines (AA 1469)
        • -
        • T
        • W
        • -
        • -
        • S
        • -
      • 10:45 CUN
        18:50 ORD
        8Hrs, 05m 1 Stop (GDL)
      • CUNCancun Airport 10:45 - ORD 18:50 8h 05m 1 Stop (GDL) Guadalajara
      • CUNCancun Airport 10:45
        GDLGuadalajara Airport 13:35
      • GDLGuadalajara Airport 12:35
        ORDChicago O'Hare International Airport 18:50
      • 8h 05m (1h)
      • 1 Stop GDL · Guadalajara 1h
      • VivaAerobus (VB 2142)Airbus
        VivaAerobus (VB 544)Airbus
      • VivaAerobus (VB 2142)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 11:00 CUN
        18:26 ORD
        7Hrs, 26m 1 Stop (DFW)
      • CUNCancun Airport 11:00 - ORD 18:26 7h 26m 1 Stop (DFW) Dallas
      • CUNCancun Airport 11:00
        DFWDallas/Fort Worth Intl Airport 16:00
      • DFWDallas/Fort Worth Intl Airport 14:00
        ORDChicago O'Hare International Airport 18:26
      • 7h 26m (2h)
      • 1 Stop DFW · Dallas 2h
      • American Airlines (AA 1601)Boeing 737 800
        American Airlines (AA 433)Boeing 737 800
      • American Airlines (AA 1601)
        • M
        • -
        • W
        • -
        • -
        • -
        • -
      • 11:00 CUN
        18:26 ORD
        7Hrs, 26m 1 Stop (DFW)
      • CUNCancun Airport 11:00 - ORD 18:26 7h 26m 1 Stop (DFW) Dallas
      • CUNCancun Airport 11:00
        DFWDallas/Fort Worth Intl Airport 16:00
      • DFWDallas/Fort Worth Intl Airport 14:00
        ORDChicago O'Hare International Airport 18:26
      • 7h 26m (2h)
      • 1 Stop DFW · Dallas 2h
      • American Airlines (AA 1601)Airbus
        American Airlines (AA 433)Boeing 737 800
      • American Airlines (AA 1601)
        • -
        • T
        • -
        • T
        • F
        • S
        • S
      • 11:00 CUN
        19:41 ORD
        8Hrs, 41m 1 Stop (DFW)
      • CUNCancun Airport 11:00 - ORD 19:41 8h 41m 1 Stop (DFW) Dallas
      • CUNCancun Airport 11:00
        DFWDallas/Fort Worth Intl Airport 17:15
      • DFWDallas/Fort Worth Intl Airport 14:00
        ORDChicago O'Hare International Airport 19:41
      • 8h 41m (3h 15m)
      • 1 Stop DFW · Dallas 3h 15m
      • American Airlines (AA 1601)Boeing 737 800
        American Airlines (AA 2399)Boeing 737 800
      • American Airlines (AA 1601)
        • M
        • -
        • W
        • -
        • -
        • -
        • -
      • 11:00 CUN
        19:41 ORD
        8Hrs, 41m 1 Stop (DFW)
      • CUNCancun Airport 11:00 - ORD 19:41 8h 41m 1 Stop (DFW) Dallas
      • CUNCancun Airport 11:00
        DFWDallas/Fort Worth Intl Airport 17:15
      • DFWDallas/Fort Worth Intl Airport 14:00
        ORDChicago O'Hare International Airport 19:41
      • 8h 41m (3h 15m)
      • 1 Stop DFW · Dallas 3h 15m
      • American Airlines (AA 1601)Airbus
        American Airlines (AA 2399)Boeing 737 800
      • American Airlines (AA 1601)
        • -
        • T
        • -
        • T
        • F
        • S
        • S
      • 11:10 CUN
        17:30 MDW
        6Hrs, 20m 1 Stop (ATL)
      • CUNCancun Airport 11:10 - MDW 17:30 6h 20m 1 Stop (ATL) Atlanta
      • CUNCancun Airport 11:10
        ATLAtlanta Hartsfield-Jackson Intl Airport 16:36
      • ATLAtlanta Hartsfield-Jackson Intl Airport 14:48
        MDWChicago Midway Airport 17:30
      • 6h 20m (1h 48m)
      • 1 Stop ATL · Atlanta 1h 48m
      • Delta Air Lines (DL 1963)Airbus
        Delta Air Lines (DL 1739)Airbus
      • Delta Air Lines (DL 1963)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 11:10 CUN
        19:30 ORD
        8Hrs, 20m 1 Stop (ATL)
      • CUNCancun Airport 11:10 - ORD 19:30 8h 20m 1 Stop (ATL) Atlanta
      • CUNCancun Airport 11:10
        ATLAtlanta Hartsfield-Jackson Intl Airport 18:20
      • ATLAtlanta Hartsfield-Jackson Intl Airport 14:48
        ORDChicago O'Hare International Airport 19:30
      • 8h 20m (3h 32m)
      • 1 Stop ATL · Atlanta 3h 32m
      • Delta Air Lines (DL 1963)Airbus
        Delta Air Lines (DL 2879)Boeing 737 900
      • Delta Air Lines (DL 1963)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 11:14 CUN
        18:55 ORD
        7Hrs, 41m 1 Stop (IAD)
      • CUNCancun Airport 11:14 - ORD 18:55 7h 41m 1 Stop (IAD) Washington
      • CUNCancun Airport 11:14
        IADWashington Dulles International Airport 17:34
      • IADWashington Dulles International Airport 15:30
        ORDChicago O'Hare International Airport 18:55
      • 7h 41m (2h 04m)
      • 1 Stop IAD · Washington 2h 04m
      • United Airlines (UA 1694)Boeing 737 Max 9 Passenger
        United Airlines (UA 2497)Boeing 757 200 Series
      • United Airlines (UA 1694)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 11:14 CUN
        19:05 ORD
        7Hrs, 51m 1 Stop (IAD)
      • CUNCancun Airport 11:14 - ORD 19:05 7h 51m 1 Stop (IAD) Washington
      • CUNCancun Airport 11:14
        IADWashington Dulles International Airport 17:44
      • IADWashington Dulles International Airport 15:30
        ORDChicago O'Hare International Airport 19:05
      • 7h 51m (2h 14m)
      • 1 Stop IAD · Washington 2h 14m
      • United Airlines (UA 1694)Boeing 737 Max 9 Passenger
        United Airlines (UA 2497)Boeing 757 200 Series
      • United Airlines (UA 1694)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 11:55 CUN
        19:44 ORD
        7Hrs, 49m 1 Stop (AUS)
      • CUNCancun Airport 11:55 - ORD 19:44 7h 49m 1 Stop (AUS) Austin
      • CUNCancun Airport 11:55
        AUSAustin-Bergstrom International Airport 16:57
      • AUSAustin-Bergstrom International Airport 14:40
        ORDChicago O'Hare International Airport 19:44
      • 7h 49m (2h 17m)
      • 1 Stop AUS · Austin 2h 17m
      • American Airlines (AA 2588)Boeing 737 800
        American Airlines (AA 1398)Boeing 737 800
      • American Airlines (AA 2588)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 12:00 CUN
        19:59 ORD
        7Hrs, 59m 1 Stop (CLT)
      • CUNCancun Airport 12:00 - ORD 19:59 7h 59m 1 Stop (CLT) Charlotte
      • CUNCancun Airport 12:00
        CLTCharlotte Airport 18:50
      • CLTCharlotte Airport 16:00
        ORDChicago O'Hare International Airport 19:59
      • 7h 59m (2h 50m)
      • 1 Stop CLT · Charlotte 2h 50m
      • American Airlines (AA 1102)Airbus
        American Airlines (AA 1076)Airbus
      • American Airlines (AA 1102)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 12:05 CUN
        19:41 ORD
        7Hrs, 36m 1 Stop (DFW)
      • CUNCancun Airport 12:05 - ORD 19:41 7h 36m 1 Stop (DFW) Dallas
      • CUNCancun Airport 12:05
        DFWDallas/Fort Worth Intl Airport 17:15
      • DFWDallas/Fort Worth Intl Airport 15:05
        ORDChicago O'Hare International Airport 19:41
      • 7h 36m (2h 10m)
      • 1 Stop DFW · Dallas 2h 10m
      • American Airlines (AA 1068)Airbus
        American Airlines (AA 2399)Boeing 737 800
      • American Airlines (AA 1068)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 12:10 CUN
        20:56 ORD
        8Hrs, 46m 1 Stop (FLL)
      • CUNCancun Airport 12:10 - ORD 20:56 8h 46m 1 Stop (FLL) Miami
      • CUNCancun Airport 12:10
        FLLFort Lauderdale/Hollywood Intl Airport 18:35
      • FLLFort Lauderdale/Hollywood Intl Airport 14:55
        ORDChicago O'Hare International Airport 20:56
      • 8h 46m (3h 40m)
      • 1 Stop FLL · Miami 3h 40m
      • Spirit Airlines (NK 1611)Airbus Industrie A321 Sharklets
        Spirit Airlines (NK 3)Airbus Industrie A321 Sharklets
      • Spirit Airlines (NK 1611)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 12:25 CUN
        19:30 ORD
        7Hrs, 05m 1 Stop (ATL)
      • CUNCancun Airport 12:25 - ORD 19:30 7h 05m 1 Stop (ATL) Atlanta
      • CUNCancun Airport 12:25
        ATLAtlanta Hartsfield-Jackson Intl Airport 18:20
      • ATLAtlanta Hartsfield-Jackson Intl Airport 16:04
        ORDChicago O'Hare International Airport 19:30
      • 7h 05m (2h 16m)
      • 1 Stop ATL · Atlanta 2h 16m
      • Delta Air Lines (DL 641)Boeing 757
        Delta Air Lines (DL 2879)Boeing 737 900
      • Delta Air Lines (DL 641)
        • -
        • T
        • -
        • -
        • -
        • S
        • -
      • 12:25 CUN
        20:44 ORD
        8Hrs, 19m 1 Stop (PHL)
      • CUNCancun Airport 12:25 - ORD 20:44 8h 19m 1 Stop (PHL) Philadelphia
      • CUNCancun Airport 12:25
        PHLPhiladelphia International Airport 19:00
      • PHLPhiladelphia International Airport 17:10
        ORDChicago O'Hare International Airport 20:44
      • 8h 19m (1h 50m)
      • 1 Stop PHL · Philadelphia 1h 50m
      • American Airlines (AA 2175)Airbus A321 Neo
        American Airlines (AA 865)Airbus
      • American Airlines (AA 2175)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 12:25 CUN
        20:59 ORD
        8Hrs, 34m 1 Stop (ATL)
      • CUNCancun Airport 12:25 - ORD 20:59 8h 34m 1 Stop (ATL) Atlanta
      • CUNCancun Airport 12:25
        ATLAtlanta Hartsfield-Jackson Intl Airport 19:55
      • ATLAtlanta Hartsfield-Jackson Intl Airport 16:04
        ORDChicago O'Hare International Airport 20:59
      • 8h 34m (3h 51m)
      • 1 Stop ATL · Atlanta 3h 51m
      • Delta Air Lines (DL 641)Boeing 757
        Delta Air Lines (DL 1139)Boeing 737 900
      • Delta Air Lines (DL 641)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 12:25 CUN
        20:59 ORD
        8Hrs, 34m 1 Stop (ATL)
      • CUNCancun Airport 12:25 - ORD 20:59 8h 34m 1 Stop (ATL) Atlanta
      • CUNCancun Airport 12:25
        ATLAtlanta Hartsfield-Jackson Intl Airport 19:55
      • ATLAtlanta Hartsfield-Jackson Intl Airport 16:04
        ORDChicago O'Hare International Airport 20:59
      • 8h 34m (3h 51m)
      • 1 Stop ATL · Atlanta 3h 51m
      • Delta Air Lines (DL 641)Boeing 757
        Delta Air Lines (DL 1577)Boeing 737 900
      • Delta Air Lines (DL 641)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 12:25 CUN
        21:11 ORD
        8Hrs, 46m 1 Stop (PHL)
      • CUNCancun Airport 12:25 - ORD 21:11 8h 46m 1 Stop (PHL) Philadelphia
      • CUNCancun Airport 12:25
        PHLPhiladelphia International Airport 19:35
      • PHLPhiladelphia International Airport 17:10
        ORDChicago O'Hare International Airport 21:11
      • 8h 46m (2h 25m)
      • 1 Stop PHL · Philadelphia 2h 25m
      • American Airlines (AA 2175)Airbus
        American Airlines (AA 1359)Boeing 737 800
      • American Airlines (AA 2175)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 12:25 CUN
        21:11 ORD
        8Hrs, 46m 1 Stop (PHL)
      • CUNCancun Airport 12:25 - ORD 21:11 8h 46m 1 Stop (PHL) Philadelphia
      • CUNCancun Airport 12:25
        PHLPhiladelphia International Airport 19:35
      • PHLPhiladelphia International Airport 17:10
        ORDChicago O'Hare International Airport 21:11
      • 8h 46m (2h 25m)
      • 1 Stop PHL · Philadelphia 2h 25m
      • American Airlines (AA 2175)Airbus A321 Neo
        American Airlines (AA 1359)Boeing 737 800
      • American Airlines (AA 2175)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 12:29 CUN
        21:01 ORD
        8Hrs, 32m 1 Stop (DTW)
      • CUNCancun Airport 12:29 - ORD 21:01 8h 32m 1 Stop (DTW) Detroit
      • CUNCancun Airport 12:29
        DTWDetroit Wayne County 20:40
      • DTWDetroit Wayne County 17:15
        ORDChicago O'Hare International Airport 21:01
      • 8h 32m (3h 25m)
      • 1 Stop DTW · Detroit 3h 25m
      • Delta Air Lines (DL 618)Boeing 737 900
        Delta Air Lines (DL 1665)Boeing 717
      • Delta Air Lines (DL 618)
        • M
        • -
        • W
        • T
        • F
        • S
        • S
      • 12:50 CUN
        19:20 MDW
        6Hrs, 30m 1 Stop (MCO)
      • CUNCancun Airport 12:50 - MDW 19:20 6h 30m 1 Stop (MCO) Orlando
      • CUNCancun Airport 12:50
        MCOOrlando International Airport 17:35
      • MCOOrlando International Airport 15:55
        MDWChicago Midway Airport 19:20
      • 6h 30m (1h 40m)
      • 1 Stop MCO · Orlando 1h 40m
      • Southwest Airlines (WN 1025)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 3662)Boeing 737 800
      • Southwest Airlines (WN 1025)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 12:50 CUN
        19:35 MDW
        6Hrs, 45m 1 Stop (MCO)
      • CUNCancun Airport 12:50 - MDW 19:35 6h 45m 1 Stop (MCO) Orlando
      • CUNCancun Airport 12:50
        MCOOrlando International Airport 17:50
      • MCOOrlando International Airport 15:55
        MDWChicago Midway Airport 19:35
      • 6h 45m (1h 55m)
      • 1 Stop MCO · Orlando 1h 55m
      • Southwest Airlines (WN 1025)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 4059)Boeing 737 800
      • Southwest Airlines (WN 1025)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 12:50 CUN
        19:55 MDW
        7Hrs, 05m 1 Stop (HOU)
      • CUNCancun Airport 12:50 - MDW 19:55 7h 05m 1 Stop (HOU) Houston
      • CUNCancun Airport 12:50
        HOUHouston Hobby Airport 17:20
      • HOUHouston Hobby Airport 15:10
        MDWChicago Midway Airport 19:55
      • 7h 05m (2h 10m)
      • 1 Stop HOU · Houston 2h 10m
      • Southwest Airlines (WN 328)Boeing 737 700
        Southwest Airlines (WN 1372)Boeing 737 800
      • Southwest Airlines (WN 328)
        • M
        • -
        • -
        • T
        • F
        • -
        • -
      • 12:50 CUN
        20:00 MDW
        7Hrs, 10m 1 Stop (MCO)
      • CUNCancun Airport 12:50 - MDW 20:00 7h 10m 1 Stop (MCO) Orlando
      • CUNCancun Airport 12:50
        MCOOrlando International Airport 18:10
      • MCOOrlando International Airport 15:55
        MDWChicago Midway Airport 20:00
      • 7h 10m (2h 15m)
      • 1 Stop MCO · Orlando 2h 15m
      • Southwest Airlines (WN 1025)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2940)Boeing 737 800
      • Southwest Airlines (WN 1025)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:50 CUN
        20:35 MDW
        7Hrs, 45m 1 Stop (MCO)
      • CUNCancun Airport 12:50 - MDW 20:35 7h 45m 1 Stop (MCO) Orlando
      • CUNCancun Airport 12:50
        MCOOrlando International Airport 18:50
      • MCOOrlando International Airport 15:55
        MDWChicago Midway Airport 20:35
      • 7h 45m (2h 55m)
      • 1 Stop MCO · Orlando 2h 55m
      • Southwest Airlines (WN 1025)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2665)Boeing 737 700
      • Southwest Airlines (WN 1025)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 12:50 CUN
        20:40 MDW
        7Hrs, 50m 1 Stop (HOU)
      • CUNCancun Airport 12:50 - MDW 20:40 7h 50m 1 Stop (HOU) Houston
      • CUNCancun Airport 12:50
        HOUHouston Hobby Airport 18:05
      • HOUHouston Hobby Airport 15:10
        MDWChicago Midway Airport 20:40
      • 7h 50m (2h 55m)
      • 1 Stop HOU · Houston 2h 55m
      • Southwest Airlines (WN 328)Boeing 737 700
        Southwest Airlines (WN 1402)Boeing 737 700
      • Southwest Airlines (WN 328)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 12:50 CUN
        21:25 MDW
        8Hrs, 35m 1 Stop (MCO)
      • CUNCancun Airport 12:50 - MDW 21:25 8h 35m 1 Stop (MCO) Orlando
      • CUNCancun Airport 12:50
        MCOOrlando International Airport 19:40
      • MCOOrlando International Airport 15:55
        MDWChicago Midway Airport 21:25
      • 8h 35m (3h 45m)
      • 1 Stop MCO · Orlando 3h 45m
      • Southwest Airlines (WN 1025)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2665)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1025)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:55 CUN
        19:20 MDW
        6Hrs, 25m 1 Stop (HOU)
      • CUNCancun Airport 12:55 - MDW 19:20 6h 25m 1 Stop (HOU) Houston
      • CUNCancun Airport 12:55
        HOUHouston Hobby Airport 16:50
      • HOUHouston Hobby Airport 15:15
        MDWChicago Midway Airport 19:20
      • 6h 25m (1h 35m)
      • 1 Stop HOU · Houston 1h 35m
      • Southwest Airlines (WN 328)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 2427)Boeing 737 700
      • Southwest Airlines (WN 328)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 12:55 CUN
        21:35 MDW
        8Hrs, 40m 1 Stop (HOU)
      • CUNCancun Airport 12:55 - MDW 21:35 8h 40m 1 Stop (HOU) Houston
      • CUNCancun Airport 12:55
        HOUHouston Hobby Airport 19:00
      • HOUHouston Hobby Airport 15:15
        MDWChicago Midway Airport 21:35
      • 8h 40m (3h 45m)
      • 1 Stop HOU · Houston 3h 45m
      • Southwest Airlines (WN 328)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1372)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 328)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 13:05 CUN
        20:15 MDW
        7Hrs, 10m 1 Stop (BWI)
      • CUNCancun Airport 13:05 - MDW 20:15 7h 10m 1 Stop (BWI) Baltimore
      • CUNCancun Airport 13:05
        BWIBaltimore Washington International Airport 19:15
      • BWIBaltimore Washington International Airport 17:35
        MDWChicago Midway Airport 20:15
      • 7h 10m (1h 40m)
      • 1 Stop BWI · Baltimore 1h 40m
      • Southwest Airlines (WN 1610)Boeing 737 700
        Southwest Airlines (WN 2606)Boeing 737 800
      • Southwest Airlines (WN 1610)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 13:05 CUN
        21:30 ORD
        8Hrs, 25m 1 Stop (BWI)
      • CUNCancun Airport 13:05 - ORD 21:30 8h 25m 1 Stop (BWI) Baltimore
      • CUNCancun Airport 13:05
        BWIBaltimore Washington International Airport 20:20
      • BWIBaltimore Washington International Airport 17:35
        ORDChicago O'Hare International Airport 21:30
      • 8h 25m (2h 45m)
      • 1 Stop BWI · Baltimore 2h 45m
      • Southwest Airlines (WN 1610)Boeing 737 700
        Southwest Airlines (WN 2708)Boeing 737 800
      • Southwest Airlines (WN 1610)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 13:05 CUN
        21:55 MDW
        8Hrs, 50m 1 Stop (BWI)
      • CUNCancun Airport 13:05 - MDW 21:55 8h 50m 1 Stop (BWI) Baltimore
      • CUNCancun Airport 13:05
        BWIBaltimore Washington International Airport 20:55
      • BWIBaltimore Washington International Airport 17:35
        MDWChicago Midway Airport 21:55
      • 8h 50m (3h 20m)
      • 1 Stop BWI · Baltimore 3h 20m
      • Southwest Airlines (WN 1610)Boeing 737 700
        Southwest Airlines (WN 4971)Boeing 737 800
      • Southwest Airlines (WN 1610)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 13:12 CUN
        20:02 ORD
        6Hrs, 50m 1 Stop (IAH)
      • CUNCancun Airport 13:12 - ORD 20:02 6h 50m 1 Stop (IAH) Houston
      • CUNCancun Airport 13:12
        IAHHouston George Bush Intercontinental Airport 17:15
      • IAHHouston George Bush Intercontinental Airport 15:40
        ORDChicago O'Hare International Airport 20:02
      • 6h 50m (1h 35m)
      • 1 Stop IAH · Houston 1h 35m
      • United Airlines (UA 1081)Boeing 737 900
        United Airlines (UA 2406)Boeing 737 900
      • United Airlines (UA 1081)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 13:12 CUN
        21:07 ORD
        7Hrs, 55m 1 Stop (IAH)
      • CUNCancun Airport 13:12 - ORD 21:07 7h 55m 1 Stop (IAH) Houston
      • CUNCancun Airport 13:12
        IAHHouston George Bush Intercontinental Airport 18:20
      • IAHHouston George Bush Intercontinental Airport 15:40
        ORDChicago O'Hare International Airport 21:07
      • 7h 55m (2h 40m)
      • 1 Stop IAH · Houston 2h 40m
      • United Airlines (UA 1081)Boeing 737 900
        United Airlines (UA 787)Boeing 737 900
      • United Airlines (UA 1081)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
      What’s the fastest flight time from Cancun to Chicago?

      The fastest flight time for direct flights from Cancun to Chicago is 3 hours 35 minutes. Check latest flight schedules & prices on Wego.

      How far is Chicago from Cancun?

      The flight distance between Cancun and Chicago 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 06:00. The last flight of the day departs at 19:00. See the full list of flight times on Wego.

      How many airlines offer direct flights from Cancun to Chicago?

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

      All Airports in Cancun

      Cancun Airport CUN

      Popular Destinations from Chicago

      Popular Destinations from Cancun

      Popular Hotels in Chicago

      Hotels In Popular Destinations