Cheap Flights from Chicago to Grand Cayman from £111️ (CHI-GCM)

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Latest Flight Deals from Chicago to Grand Cayman

Book one-way or return flights from Chicago to Grand Cayman from as little as £111. Choose from the popular airlines below and book your flight today!

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from Chicago to Grand Cayman? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Chicago to Grand Cayman. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Airlines Flying from Chicago to Grand Cayman

View airlines operating flights from Chicago to Grand Cayman. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines

From £111

Spirit Airlines

From £131

Jetblue Airways

From £144

American Airlines

From £155

Air Canada

From £163

United Airlines

From £168

Delta Air Lines

From £216

Copa Airlines

From £903

ANA airlines

Find more flights and airlines

Alternative Routes from Chicago to Grand Cayman

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Chicago to Grand Cayman.

Cheapest
MDW
19:13
20h 57m
1 transfer
GCM
16:10
Midway International Airport - Owen Roberts International Airport
Tue, May 7Frontier Airlines
£111
ORD
17:19
17h 1m
1 transfer
GCM
10:20
O'Hare International Airport - Owen Roberts International Airport
Tue, May 21Spirit Airlines
£131
ORD
17:19
17h 1m
1 transfer
GCM
10:20
O'Hare International Airport - Owen Roberts International Airport
Tue, May 21Spirit Airlines
£131
Find More Flights

How do I find the cheapest flights?

When are flight tickets from Chicago (CHI) to Grand Cayman (GCM) the cheapest?
Airlines adjust prices for flights from Chicago to Grand Cayman based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Chicago (CHI) to Grand Cayman (GCM) cost?
According to Trip.com's data, the lowest price is around £542.
How long is the flight from Chicago (CHI) to Grand Cayman (GCM)?
It takes about 4 hours 2 minutes to fly from Chicago (CHI) to Grand Cayman (GCM).
What is the transportation method from the main airport to downtown in Grand Cayman?
- The distance from Owen Roberts International Airport to downtown is about 11km, by taxi about 30 minutes.
What are the most popular airlines that fly from Chicago (CHI) to Grand Cayman (GCM)?
Airlines with flights from Chicago (CHI) to Grand Cayman (GCM): United Airlines.
What's the most popular airline for direct flights from Chicago (CHI) to Grand Cayman (GCM)?
United Airlines operates 1 direct flights from Chicago (CHI) to Grand Cayman (GCM).
How many airports in Grand Cayman (GCM)?
There are 1 airport(s) in Grand Cayman (GCM): Owen Roberts International Airport.

How to find a cheap flight from Chicago to Grand Cayman

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Grand Cayman. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

Save up to £10 per person when booking your flights on Trip.com

Flight Information from Chicago to Grand Cayman

Cheapest direct flight price	£111
Cheapest return ticket price	£487
Cheapest month	April
Peak season for travel	July
Flight distance	2,580.07km
Average flight time	4 hours 2 minutes
Popular airline	United Airlines