Cheap flights from Chicago, IL to Grand Cayman, Cayman Islands
Flights starting at $150. Choose between United Airlines, Cayman Airways, or Spirit Airlines to find the best price.
Make your travel wishlist, we'll do the rest
Hidden deals
Kiwi-Code uncovers prices airlines don't want you to see.
Effortless booking
Use our flexible filters to tailor your search.
Travel hacking
Look out for the travel hack star icon for even cheaper fares.
Tips to know when travelling to Grand Cayman
Search by stops
Search by price
Search by departure date
One-way trips
Updated:
Round trips
Updated:
Receive exclusive deals by email
By subscribing you agree to receive offers according to the conditions described in our Privacy Policy.
Travelers usually depart from O Hare International, Chicago Midway International, or Chicago Rockford International when they travel from Chicago to Grand Cayman. The distance between Chicago and Grand Cayman is 2600 km. The most popular airlines for this route are United Airlines, Cayman Airways, Spirit Airlines, JetBlue Airways, and Frontier Airlines. Chicago and Grand Cayman have 91 direct flights per week.
Weekly direct flights
Discover the top airlines offering direct flights from Chicago to Grand Cayman in the next month. You’ll find the number of daily direct flights per airline in the table.
Weekly direct flights for Sun 28.04 - Sat 04.05
| Airline | Sun 28.04 | Mon 29.04 | Tue 30.04 | Wed 01.05 | Thu 02.05 | Fri 03.05 | Sat 04.05 |
|---|---|---|---|---|---|---|---|
| 1 | --- | --- | --- | --- | --- | 1 |
Weekly direct flights for Sun 05.05 - Sat 11.05
| Airline | Sun 05.05 | Mon 06.05 | Tue 07.05 | Wed 08.05 | Thu 09.05 | Fri 10.05 | Sat 11.05 |
|---|---|---|---|---|---|---|---|
| --- | --- | --- | --- | --- | --- | 1 |
Weekly direct flights for Sun 12.05 - Sat 18.05
| Airline | Sun 12.05 | Mon 13.05 | Tue 14.05 | Wed 15.05 | Thu 16.05 | Fri 17.05 | Sat 18.05 |
|---|---|---|---|---|---|---|---|
| --- | --- | --- | --- | --- | --- | 1 |
Weekly direct flights for Sun 19.05 - Sat 25.05
| Airline | Sun 19.05 | Mon 20.05 | Tue 21.05 | Wed 22.05 | Thu 23.05 | Fri 24.05 | Sat 25.05 |
|---|---|---|---|---|---|---|---|
| --- | --- | --- | --- | --- | --- | 1 |
Check-in for a flight from Chicago to Grand Cayman
| Name | Carrier code | IATA Code | Passport needed during booking | Online check-in available |
|---|---|---|---|---|
| United Airlines | UAL | UA | Yes | No |
| Cayman Airways | CAY | KX | Yes | No |
| Spirit Airlines | NKS | NK | No | Opens 24 days before flight Closes 1 hours before flight |
| JetBlue Airways | JBU | B6 | No | Opens 24 days before flight Closes 2 hours before flight |
| Frontier Airlines | FFT | F9 | No | Opens 24 days before flight Closes 1 hours before flight |
Weather in Grand Cayman
Average Weather
| Month | Average monthly max temperature | Average monthly min temperature |
| January | 26°C | 25°C |
| February | 26°C | 25°C |
| March | 26°C | 25°C |
| April | 27°C | 26°C |
| May | 28°C | 27°C |
| June | 28°C | 27°C |
| July | 29°C | 28°C |
| August | 29°C | 28°C |
| September | 29°C | 28°C |
| October | 29°C | 27°C |
| November | 27°C | 26°C |
| December | 27°C | 26°C |
14 day forecast
Frequently asked questions
Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any A and any B in the world by plane, train, and bus. Find the cheapest routes and best deals for you, as well as the best dates on which to travel.
Explore alternative trips
Flights from Chicago
- Flights from Chicago to Las Vegas
- Flights from Chicago to Guadalajara
- Flights from Chicago to Denver
- Flights from Chicago to Orlando
- Flights from Chicago to Phoenix
- Flights from Chicago to Mexico City
- Flights from Chicago to Paris
- Flights from Chicago to Barcelona
- Flights from Chicago to Tampa
- Flights from Chicago to Miami
- Flights from Chicago to London
- Flights from Chicago to Rome
- Flights from Chicago to Los Angeles
- Flights from Chicago to Madrid
- Flights from Chicago to Fort Myers
- Flights from Chicago to Athens
- Flights from Chicago to San Francisco
- Flights from Chicago to New York
- Flights from Chicago to Austin
- Flights from Chicago to Atlanta
Flights to Grand Cayman
- Flights from Minneapolis to Grand Cayman
- Flights from London to Grand Cayman
- Flights from Detroit to Grand Cayman
- Flights from Atlanta to Grand Cayman
- Flights from Denver to Grand Cayman
- Flights from New York to Grand Cayman
- Flights from Philadelphia to Grand Cayman
- Flights from Miami to Grand Cayman
- Flights from Dallas to Grand Cayman
- Flights from Mexico City to Grand Cayman
- Flights from Cancún to Grand Cayman
- Flights from Seattle to Grand Cayman
- Flights from Paris to Grand Cayman
- Flights from Charlotte to Grand Cayman
- Flights from San Francisco to Grand Cayman
- Flights from Fort Lauderdale to Grand Cayman
- Flights from Dubai to Grand Cayman
- Flights from San José to Grand Cayman
- Flights from Nassau to Grand Cayman
- Flights from Panama to Grand Cayman
Popular routes
- Flights from Riyadh to Prague
- Flights from Dubai to Vijayawada
- Flights from Barcelona to Buenos Aires
- Flights from Providence to Key West
- Flights from Tehran to Chicago
- Flights from Honolulu to Guatemala City
- Flights from Denver to Accra
- Flights from Kuching to Bangkok
- Flights from Guadalajara to Toluca
- Flights from Chicago to Las Vegas
- Flights from Chicago to Denver
- Flights from Washington, D.C. to Denver
- Flights from Milan to Lima
Airports near Chicago
- O Hare International
- Chicago Midway International
- Gerald R. Ford International
- General Mitchell International
- Dane County Regional
- Chicago Rockford International
- South Bend International
- Quad City International
- Fort Wayne International
- General Wayne A. Downing Peoria International