Cheap flights from Grand Cayman, Cayman Islands to Chicago, IL
Flights starting at £206. Choose between Cayman Airways, United Airlines, 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 Chicago
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.
Book your trip to arrive at O Hare International, Chicago Midway International, or Chicago Rockford International. The distance between Grand Cayman and Chicago is 2600 km. The most popular airlines for this route are Cayman Airways, United Airlines, Spirit Airlines, Frontier Airlines, and JetBlue Airways. Grand Cayman and Chicago have 118 direct flights per week.
Weekly direct flights
Discover the top airlines offering direct flights from Grand Cayman to Chicago in the next month. You’ll find the number of daily direct flights per airline in the table.
Weekly direct flights for Mon 29.04 - Sun 05.05
Airline | Mon 29.04 | Tue 30.04 | Wed 01.05 | Thu 02.05 | Fri 03.05 | Sat 04.05 | Sun 05.05 |
---|---|---|---|---|---|---|---|
--- | --- | --- | --- | --- | 1 | --- |
Weekly direct flights for Mon 06.05 - Sun 12.05
Airline | Mon 06.05 | Tue 07.05 | Wed 08.05 | Thu 09.05 | Fri 10.05 | Sat 11.05 | Sun 12.05 |
---|---|---|---|---|---|---|---|
--- | --- | --- | --- | --- | 1 | --- |
Weekly direct flights for Mon 13.05 - Sun 19.05
Airline | Mon 13.05 | Tue 14.05 | Wed 15.05 | Thu 16.05 | Fri 17.05 | Sat 18.05 | Sun 19.05 |
---|---|---|---|---|---|---|---|
--- | --- | --- | --- | --- | 1 | --- |
Weekly direct flights for Mon 20.05 - Sun 26.05
Airline | Mon 20.05 | Tue 21.05 | Wed 22.05 | Thu 23.05 | Fri 24.05 | Sat 25.05 | Sun 26.05 |
---|---|---|---|---|---|---|---|
--- | --- | --- | --- | --- | 1 | 1 |
Check-in for a flight from Grand Cayman to Chicago
Name | Carrier code | IATA Code | Passport needed during booking | Online check-in available |
---|---|---|---|---|
Cayman Airways | CAY | KX | Yes | No |
United Airlines | UAL | UA | Yes | No |
Spirit Airlines | NKS | NK | No | Opens 24 days before flight Closes 1 hours before flight |
Frontier Airlines | FFT | F9 | 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 |
Weather in Chicago
Average Weather
Month | Average monthly max temperature | Average monthly min temperature |
January | 0°C | -6°C |
February | 0°C | -5°C |
March | 6°C | 0°C |
April | 10°C | 4°C |
May | 17°C | 10°C |
June | 22°C | 16°C |
July | 25°C | 20°C |
August | 25°C | 19°C |
September | 22°C | 16°C |
October | 15°C | 10°C |
November | 8°C | 3°C |
December | 2°C | -1°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 Grand Cayman
- Flights from Grand Cayman to London
- Flights from Grand Cayman to Dublin
- Flights from Grand Cayman to Manchester
- Flights from Grand Cayman to Mexico City
- Flights from Grand Cayman to New York
- Flights from Grand Cayman to Miami
- Flights from Grand Cayman to Willemstad
- Flights from Grand Cayman to Toronto
- Flights from Grand Cayman to Bangkok
- Flights from Grand Cayman to Taipei
- Flights from Grand Cayman to Calgary
- Flights from Grand Cayman to Vancouver
- Flights from Grand Cayman to Los Angeles
- Flights from Grand Cayman to Edinburgh
- Flights from Grand Cayman to San José del Cabo
- Flights from Grand Cayman to Newcastle upon Tyne
- Flights from Grand Cayman to Houston
- Flights from Grand Cayman to Manila
- Flights from Grand Cayman to Barcelona
- Flights from Grand Cayman to Vienna
Flights to Chicago
- Flights from London to Chicago
- Flights from Dublin to Chicago
- Flights from Manchester to Chicago
- Flights from Toronto to Chicago
- Flights from Athens to Chicago
- Flights from Orlando to Chicago
- Flights from San Francisco to Chicago
- Flights from Hyderabad to Chicago
- Flights from New York to Chicago
- Flights from Las Vegas to Chicago
- Flights from Edinburgh to Chicago
- Flights from Denver to Chicago
- Flights from Bangkok to Chicago
- Flights from Minneapolis to Chicago
- Flights from Riga to Chicago
- Flights from Glasgow to Chicago
- Flights from Austin to Chicago
- Flights from San Juan to Chicago
- Flights from Edmonton to Chicago
- Flights from Tallinn to Chicago
Popular routes
- Flights from Chiang Mai to Bangkok
- Flights from Florianópolis to Goiânia
- Flights from Singapore to Bora Bora
- Flights from Gdańsk to New York
- Flights from Chicago to Grand Cayman
- Flights from Salalah to Cincinnati
- Flights from San Diego to Puebla
- Flights from Phoenix to Macau
- Flights from Tallahassee to Panama
- Flights from El Paso to Islip
- Flights from Stockholm to Tambor
- Flights from Phuket City to Bangkok