Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline United Airlines

The cheapest airline(s) flying from Chicago to Grand Cayman Island is United Airlines.

  • United Airlines United Airlines
  • JetBlue Airways JetBlue Airways
  • American Airlines American Airlines
  • Air Canada Air Canada
Cheapest Month December

Travel Period: December 2024 - November 2025

The cheapest month(s) to fly from Chicago to Grand Cayman Island is December.

  • 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 Friday

The cheapest day(s) of the week to fly from Chicago to Grand Cayman Island is Friday.

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

Flight Schedules

Last Updated: Sat, 2 Nov, 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
      • 08:39 ORD
        13:35 GCM
        3Hrs, 56m Direct
      • ORDChicago O'Hare International Airport 08:39 - GCM 13:35 3h 56m Direct
      • ORDChicago O'Hare International Airport 08:39
      • GCMGrand Cayman Island Airport 13:35
      • 3h 56m
      • Direct
      • United Airlines (UA 322)Boeing 737 800
      • United Airlines (UA 322)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • Boeing 737 800
      • 05:00 ORD
        14:15 GCM
        8Hrs, 15m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 05:00 - GCM 14:15 8h 15m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 05:00
        MIAMiami International Airport 12:25
      • MIAMiami International Airport 09:07
        GCMGrand Cayman Island Airport 14:15
      • 8h 15m (3h 18m)
      • 1 Stop MIA · Miami 3h 18m
      • American Airlines (AA 2984)Boeing 737 800
        American Airlines (AA 956)Boeing 737 800
      • American Airlines (AA 2984)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 12:25 MIA
        07:56 CLT
        8Hrs, 15m 1 Stop (GCM)
      • MIAMiami International Airport 12:25 - CLT 07:56 8h 15m 1 Stop (GCM) Grand Cayman Island
      • MIAMiami International Airport 12:25
        ORDChicago O'Hare International Airport 05:00
      • GCMGrand Cayman Island Airport 14:15
        CLTCharlotte Airport 07:56
      • 8h 15m (2h 25m)
      • 1 Stop GCM · Grand Cayman Island 2h 25m
      • American Airlines (AA 956)Boeing 737 800
        American Airlines (AA 2842)Boeing 737 Max 8 Passenger
      • American Airlines (AA 956)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:25 MIA
        07:55 CLT
        8Hrs, 15m 1 Stop (GCM)
      • MIAMiami International Airport 12:25 - CLT 07:55 8h 15m 1 Stop (GCM) Grand Cayman Island
      • MIAMiami International Airport 12:25
        ORDChicago O'Hare International Airport 05:00
      • GCMGrand Cayman Island Airport 14:15
        CLTCharlotte Airport 07:55
      • 8h 15m (2h 26m)
      • 1 Stop GCM · Grand Cayman Island 2h 26m
      • American Airlines (AA 956)Boeing 737 800
        American Airlines (AA 2842)Boeing 737 Max 8 Passenger
      • American Airlines (AA 956)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:00 ORD
        14:05 GCM
        8Hrs, 05m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:00 - GCM 14:05 8h 05m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:00
        CLTCharlotte Airport 11:05
      • CLTCharlotte Airport 07:56
        GCMGrand Cayman Island Airport 14:05
      • 8h 05m (3h 09m)
      • 1 Stop CLT · Charlotte 3h 09m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 350)Boeing 737 800
      • American Airlines (AA 2842)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:00 ORD
        12:35 GCM
        6Hrs, 35m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:00 - GCM 12:35 6h 35m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:00
        CLTCharlotte Airport 09:35
      • CLTCharlotte Airport 07:55
        GCMGrand Cayman Island Airport 12:35
      • 6h 35m (1h 40m)
      • 1 Stop CLT · Charlotte 1h 40m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 301)Boeing 737 800
      • American Airlines (AA 2842)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:00 ORD
        12:35 GCM
        6Hrs, 35m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:00 - GCM 12:35 6h 35m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:00
        CLTCharlotte Airport 09:35
      • CLTCharlotte Airport 07:56
        GCMGrand Cayman Island Airport 12:35
      • 6h 35m (1h 39m)
      • 1 Stop CLT · Charlotte 1h 39m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 301)Boeing 737 800
      • American Airlines (AA 2842)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:00 ORD
        12:00 GCM
        6Hrs, 00m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 05:00 - GCM 12:00 6h 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 05:00
        MIAMiami International Airport 10:15
      • MIAMiami International Airport 09:07
        GCMGrand Cayman Island Airport 12:00
      • 6h (1h 08m)
      • 1 Stop MIA · Miami 1h 08m
      • American Airlines (AA 2984)Boeing 737 800
        American Airlines (AA 1300)Airbus
      • American Airlines (AA 2984)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 05:00 ORD
        12:30 GCM
        6Hrs, 30m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 05:00 - GCM 12:30 6h 30m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 05:00
        CLTCharlotte Airport 09:30
      • CLTCharlotte Airport 07:56
        GCMGrand Cayman Island Airport 12:30
      • 6h 30m (1h 34m)
      • 1 Stop CLT · Charlotte 1h 34m
      • American Airlines (AA 2842)Boeing 737 Max 8 Passenger
        American Airlines (AA 301)Boeing 737 800
      • American Airlines (AA 2842)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:10 MDW
        12:55 GCM
        6Hrs, 45m 1 Stop (MCO)
      • MDWChicago Midway Airport 05:10 - GCM 12:55 6h 45m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 05:10
        MCOOrlando International Airport 11:00
      • MCOOrlando International Airport 08:55
        GCMGrand Cayman Island Airport 12:55
      • 6h 45m (2h 05m)
      • 1 Stop MCO · Orlando 2h 05m
      • Southwest Airlines (WN 2538)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 912)Boeing 737 700
      • Southwest Airlines (WN 2538)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 06:00 ORD
        15:00 GCM
        8Hrs, 00m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 06:00 - GCM 15:00 8h 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 06:00
        DFWDallas/Fort Worth Intl Airport 10:25
      • DFWDallas/Fort Worth Intl Airport 08:35
        GCMGrand Cayman Island Airport 15:00
      • 8h (1h 50m)
      • 1 Stop DFW · Dallas 1h 50m
      • American Airlines (AA 482)Airbus
        American Airlines (AA 355)Boeing 737 800
      • American Airlines (AA 482)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 06:00 MDW
        12:55 GCM
        5Hrs, 55m 1 Stop (MCO)
      • MDWChicago Midway Airport 06:00 - GCM 12:55 5h 55m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 06:00
        MCOOrlando International Airport 11:00
      • MCOOrlando International Airport 09:45
        GCMGrand Cayman Island Airport 12:55
      • 5h 55m (1h 15m)
      • 1 Stop MCO · Orlando 1h 15m
      • Southwest Airlines (WN 1601)Boeing 737 800
        Southwest Airlines (WN 912)Boeing 737 700
      • Southwest Airlines (WN 1601)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 06:55 MDW
        13:20 GCM
        5Hrs, 25m 1 Stop (MCO)
      • MDWChicago Midway Airport 06:55 - GCM 13:20 5h 25m 1 Stop (MCO) Orlando
      • MDWChicago Midway Airport 06:55
        MCOOrlando International Airport 11:25
      • MCOOrlando International Airport 10:40
        GCMGrand Cayman Island Airport 13:20
      • 5h 25m (45m)
      • 1 Stop MCO · Orlando 45m
      • Southwest Airlines (WN 1301)Boeing 737 800
        Southwest Airlines (WN 912)Boeing 737 700
      • Southwest Airlines (WN 1301)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:00 ORD
        14:15 GCM
        6Hrs, 15m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 07:00 - GCM 14:15 6h 15m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 07:00
        MIAMiami International Airport 12:25
      • MIAMiami International Airport 11:05
        GCMGrand Cayman Island Airport 14:15
      • 6h 15m (1h 20m)
      • 1 Stop MIA · Miami 1h 20m
      • American Airlines (AA 1411)Boeing 737 Max 8 Passenger
        American Airlines (AA 956)Boeing 737 800
      • American Airlines (AA 1411)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 07:00 ORD
        16:29 GCM
        8Hrs, 29m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 07:00 - GCM 16:29 8h 29m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 07:00
        CLTCharlotte Airport 13:39
      • CLTCharlotte Airport 09:57
        GCMGrand Cayman Island Airport 16:29
      • 8h 29m (3h 42m)
      • 1 Stop CLT · Charlotte 3h 42m
      • American Airlines (AA 1784)Airbus
        American Airlines (AA 350)Airbus
      • American Airlines (AA 1784)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 07:00 ORD
        14:05 GCM
        6Hrs, 05m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 07:00 - GCM 14:05 6h 05m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 07:00
        CLTCharlotte Airport 11:05
      • CLTCharlotte Airport 09:56
        GCMGrand Cayman Island Airport 14:05
      • 6h 05m (1h 09m)
      • 1 Stop CLT · Charlotte 1h 09m
      • American Airlines (AA 1784)Airbus
        American Airlines (AA 350)Boeing 737 800
      • American Airlines (AA 1784)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:01 ORD
        15:00 GCM
        6Hrs, 59m 1 Stop (DFW)
      • ORDChicago O'Hare International Airport 07:01 - GCM 15:00 6h 59m 1 Stop (DFW) Dallas
      • ORDChicago O'Hare International Airport 07:01
        DFWDallas/Fort Worth Intl Airport 10:25
      • DFWDallas/Fort Worth Intl Airport 09:37
        GCMGrand Cayman Island Airport 15:00
      • 6h 59m (48m)
      • 1 Stop DFW · Dallas 48m
      • American Airlines (AA 1902)Boeing 737 800
        American Airlines (AA 355)Boeing 737 800
      • American Airlines (AA 1902)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:55 IAD
        09:41 CMH
        8Hrs, 25m 1 Stop (GCM)
      • IADWashington Dulles International Airport 12:55 - CMH 09:41 8h 25m 1 Stop (GCM) Grand Cayman Island
      • IADWashington Dulles International Airport 12:55
        ORDChicago O'Hare International Airport 07:10
      • GCMGrand Cayman Island Airport 16:35
        CMHColumbus Port Columbus Intl Airport 09:41
      • 8h 25m (1h 53m)
      • 1 Stop GCM · Grand Cayman Island 1h 53m
      • United Airlines (UA 220)Boeing 737 900
        United Airlines (UA 3584)Embraer 175
      • United Airlines (UA 220)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:55 IAD
        09:41 CVG
        8Hrs, 15m 1 Stop (GCM)
      • IADWashington Dulles International Airport 12:55 - CVG 09:41 8h 15m 1 Stop (GCM) Grand Cayman Island
      • IADWashington Dulles International Airport 12:55
        ORDChicago O'Hare International Airport 07:20
      • GCMGrand Cayman Island Airport 16:35
        CVGCincinnati Northern Kentucky Intl Airport 09:41
      • 8h 15m (1h 42m)
      • 1 Stop GCM · Grand Cayman Island 1h 42m
      • United Airlines (UA 220)Boeing 737 900
        United Airlines (UA 3498)Embraer 175
      • United Airlines (UA 220)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:55 IAD
        09:35 IND
        8Hrs, 14m 1 Stop (GCM)
      • IADWashington Dulles International Airport 12:55 - IND 09:35 8h 14m 1 Stop (GCM) Grand Cayman Island
      • IADWashington Dulles International Airport 12:55
        ORDChicago O'Hare International Airport 07:21
      • GCMGrand Cayman Island Airport 16:35
        INDIndianapolis Airport 09:35
      • 8h 14m (1h 41m)
      • 1 Stop GCM · Grand Cayman Island 1h 41m
      • United Airlines (UA 220)Boeing 737 900
        United Airlines (UA 3668)Embraer 175
      • United Airlines (UA 220)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:55 IAD
        09:52 CLE
        8Hrs, 05m 1 Stop (GCM)
      • IADWashington Dulles International Airport 12:55 - CLE 09:52 8h 05m 1 Stop (GCM) Grand Cayman Island
      • IADWashington Dulles International Airport 12:55
        ORDChicago O'Hare International Airport 07:30
      • GCMGrand Cayman Island Airport 16:35
        CLECleveland Hopkins International Airport 09:52
      • 8h 05m (1h 41m)
      • 1 Stop GCM · Grand Cayman Island 1h 41m
      • United Airlines (UA 220)Boeing 737 900
        United Airlines (UA 286)Boeing 737 700
      • United Airlines (UA 220)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:35 ORD
        16:25 GCM
        7Hrs, 50m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 07:35 - GCM 16:25 7h 50m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 07:35
        IAHHouston George Bush Intercontinental Airport 12:29
      • IAHHouston George Bush Intercontinental Airport 10:32
        GCMGrand Cayman Island Airport 16:25
      • 7h 50m (1h 57m)
      • 1 Stop IAH · Houston 1h 57m
      • United Airlines (UA 1850)Boeing 737 Max 9 Passenger
        United Airlines (UA 753)Boeing 737 900
      • United Airlines (UA 1850)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 07:35 ORD
        16:50 GCM
        8Hrs, 15m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 07:35 - GCM 16:50 8h 15m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 07:35
        IAHHouston George Bush Intercontinental Airport 12:54
      • IAHHouston George Bush Intercontinental Airport 10:32
        GCMGrand Cayman Island Airport 16:50
      • 8h 15m (2h 22m)
      • 1 Stop IAH · Houston 2h 22m
      • United Airlines (UA 1850)Boeing 737 900
        United Airlines (UA 753)Boeing 737 900
      • United Airlines (UA 1850)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 08:19 ORD
        16:29 GCM
        7Hrs, 10m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 08:19 - GCM 16:29 7h 10m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 08:19
        CLTCharlotte Airport 13:39
      • CLTCharlotte Airport 11:19
        GCMGrand Cayman Island Airport 16:29
      • 7h 10m (2h 20m)
      • 1 Stop CLT · Charlotte 2h 20m
      • American Airlines (AA 3028)Boeing 737 800
        American Airlines (AA 350)Airbus
      • American Airlines (AA 3028)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 08:50 ORD
        16:50 GCM
        7Hrs, 00m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 08:50 - GCM 16:50 7h 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 08:50
        IAHHouston George Bush Intercontinental Airport 12:54
      • IAHHouston George Bush Intercontinental Airport 11:47
        GCMGrand Cayman Island Airport 16:50
      • 7h (1h 07m)
      • 1 Stop IAH · Houston 1h 07m
      • United Airlines (UA 2851)Boeing 737 800
        United Airlines (UA 753)Boeing 737 900
      • United Airlines (UA 2851)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 08:50 ORD
        16:35 GCM
        6Hrs, 45m 1 Stop (IAD)
      • ORDChicago O'Hare International Airport 08:50 - GCM 16:35 6h 45m 1 Stop (IAD) Washington
      • ORDChicago O'Hare International Airport 08:50
        IADWashington Dulles International Airport 12:55
      • IADWashington Dulles International Airport 11:46
        GCMGrand Cayman Island Airport 16:35
      • 6h 45m (1h 09m)
      • 1 Stop IAD · Washington 1h 09m
      • United Airlines (UA 545)Boeing 737 900
        United Airlines (UA 220)Boeing 737 900
      • United Airlines (UA 545)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 08:50 ORD
        16:25 GCM
        6Hrs, 35m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 08:50 - GCM 16:25 6h 35m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 08:50
        IAHHouston George Bush Intercontinental Airport 12:29
      • IAHHouston George Bush Intercontinental Airport 11:47
        GCMGrand Cayman Island Airport 16:25
      • 6h 35m (42m)
      • 1 Stop IAH · Houston 42m
      • United Airlines (UA 2851)Boeing 737 900
        United Airlines (UA 753)Boeing 737 900
      • United Airlines (UA 2851)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
      What’s the fastest flight time from Chicago to Grand Cayman Island?

      The fastest flight time for direct flights from Chicago to Grand Cayman Island is 3 hours 56 minutes. Check latest flight schedules & prices on Wego.

      How far is Grand Cayman Island from Chicago?

      The flight distance between Chicago and Grand Cayman Island is 2580km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 05:00. The last flight of the day departs at 12:25. See the full list of flight times on Wego.

      How many airlines offer direct flights from Chicago to Grand Cayman Island?

      There are 1 airlines that offer direct flights from Chicago to Grand Cayman Island. Find out the list of airlines on Wego.

      All Airports in Grand Cayman Island

      Grand Cayman Island Airport GCM

      Popular Destinations from Grand Cayman Island

      Popular Destinations from Chicago

      Popular Hotels in Grand Cayman Island

      Hotels In Popular Destinations