Flight Routes from Chicago to Grand Cayman

Compare cheap outbound and return flights from Chicago (CHI) to Grand Cayman (GCM) and find the best offer from numerous airlines and travel agencies.

Trip type
Cheapest roundtrip flight
from€710
Fastest flight
non-stop flights
5x / week
Flight distance
2,584 km
Time difference
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL

Cheap flight offers from Chicago to Grand Cayman

sorted by price and recency
  1. –
    American Airlines
    –
    CHI–GCM
    1 stopover
    American Airlines
    –
    GCM–CHI
    non-stop flight
    €1,247
  2. –
    Air Canada
    –
    CHI–GCM
    1 stopover
    Air Canada
    –
    GCM–CHI
    1 stopover
    €994
  3. –
    United Airlines
    –
    CHI–GCM
    1 stopover
    United Airlines
    –
    GCM–CHI
    1 stopover
    €772
  4. –
    United Airlines
    –
    CHI–GCM
    1 stopover
    United Airlines
    –
    GCM–CHI
    non-stop flight
    €711
  5. –
    United Airlines
    –
    CHI–GCM
    1 stopover
    United Airlines
    –
    GCM–CHI
    1 stopover
    €710

Flight schedule from Chicago (CHI) to Grand Cayman (GCM)

Select a travel date in the flight schedule for the route from Chicago (CHI) to Grand Cayman (GCM) and compare affordable flight deals.

offers
Active filtersnone
Matching outbound flightsCHI–GCM · 3 of 3
fromto
dep.arr.
durationstopovers
  1. November 8 – 14, 2026
  2. November 15 – 21, 2026
  3. November 22 – 28, 2026
    1. ORDGCM
      nonstop
      1. American Airlines
    2. ORDGCM
      nonstop
      1. United Airlines
    3. ORDGCM
      nonstop
      1. American Airlines

      Important flight information

      Discover more flights around Chicago and Grand Cayman

      Departure airport Airport Chicago-IL, all airports (CHI)
      Arrival airport Airport Grand Cayman (GCM)
      Destination country Flights to Cayman Islands
      Departure airport - Destination country Chicago-IL, all airports - Cayman Islands
      Alternative flights to Grand Cayman
      Flight destinations with a similar price