Cheap flights from Chicago, IL to Grand Cayman, Cayman Islands
Flights starting at £119. Choose between Spirit Airlines, Cayman Airways, or United 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
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 Spirit Airlines, Cayman Airways, United Airlines, JetBlue Airways, and Frontier Airlines. Chicago and Grand Cayman have 124 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 Mon 03.06 - Sun 09.06
Airline | Mon 03.06 | Tue 04.06 | Wed 05.06 | Thu 06.06 | Fri 07.06 | Sat 08.06 | Sun 09.06 |
---|---|---|---|---|---|---|---|
--- | --- | --- | --- | --- | 1 | 1 |
Weekly direct flights for Mon 10.06 - Sun 16.06
Airline | Mon 10.06 | Tue 11.06 | Wed 12.06 | Thu 13.06 | Fri 14.06 | Sat 15.06 | Sun 16.06 |
---|---|---|---|---|---|---|---|
--- | --- | --- | --- | --- | 1 | 1 |
Weekly direct flights for Mon 17.06 - Sun 23.06
Airline | Mon 17.06 | Tue 18.06 | Wed 19.06 | Thu 20.06 | Fri 21.06 | Sat 22.06 | Sun 23.06 |
---|---|---|---|---|---|---|---|
--- | --- | --- | --- | --- | 1 | 1 |
Weekly direct flights for Mon 24.06 - Sun 30.06
Airline | Mon 24.06 | Tue 25.06 | Wed 26.06 | Thu 27.06 | Fri 28.06 | Sat 29.06 | Sun 30.06 |
---|---|---|---|---|---|---|---|
--- | --- | --- | --- | --- | 1 | 1 |
Check-in for a flight from Chicago to Grand Cayman
Name | Carrier code | IATA Code | Passport needed during booking | Online check-in available |
---|---|---|---|---|
Spirit Airlines | NKS | NK | No | Opens 24 days before flight Closes 1 hours before flight |
Cayman Airways | CAY | KX | Yes | No |
United Airlines | UAL | UA | Yes | No |
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 London
- Flights from Chicago to Manchester
- Flights from Chicago to Athens
- Flights from Chicago to Dublin
- Flights from Chicago to New York
- Flights from Chicago to Las Vegas
- Flights from Chicago to Vilnius
- Flights from Chicago to Los Angeles
- Flights from Chicago to Denver
- Flights from Chicago to Orlando
- Flights from Chicago to Minneapolis
- Flights from Chicago to Barcelona
- Flights from Chicago to Austin
- Flights from Chicago to Edinburgh
- Flights from Chicago to San Francisco
- Flights from Chicago to Paris
- Flights from Chicago to Nashville
- Flights from Chicago to Atlanta
- Flights from Chicago to Glasgow
- Flights from Chicago to Riga
Flights to Grand Cayman
- Flights from London to Grand Cayman
- Flights from Manchester to Grand Cayman
- Flights from Miami to Grand Cayman
- Flights from Dublin to Grand Cayman
- Flights from Manila to Grand Cayman
- Flights from New York to Grand Cayman
- Flights from Fort Lauderdale to Grand Cayman
- Flights from Hong Kong to Grand Cayman
- Flights from San José to Grand Cayman
- Flights from Prague to Grand Cayman
- Flights from Nassau to Grand Cayman
- Flights from New Orleans to Grand Cayman
- Flights from Newcastle upon Tyne to Grand Cayman
- Flights from Panama to Grand Cayman
- Flights from Edinburgh to Grand Cayman
- Flights from Mexico City to Grand Cayman
- Flights from Kingston to Grand Cayman
- Flights from San José del Cabo to Grand Cayman
- Flights from Bucharest to Grand Cayman
- Flights from Kharkiv to Grand Cayman
Popular routes
- Flights from London to Rome
- Flights from Florianópolis to Goiânia
- Flights from Singapore to Bora Bora
- Flights from Gdańsk to New York
- Flights from Grand Cayman to Chicago
- Flights from Salalah to Cincinnati
- Flights from San Diego to Puebla
- Flights from Phoenix to Macau
- Flights from El Paso to Islip
- Flights from Stockholm to Tambor
- Flights from Toronto to Vancouver
- Flights from Des Moines to Huntsville
Airports near Chicago
- O Hare International
- Chicago Midway International
- Gerald R. Ford International
- General Mitchell International
- Chicago Rockford International
- Dane County Regional
- South Bend International
- Fort Wayne International
- Quad City International
- General Wayne A. Downing Peoria International