Cheap Flights from Grand Cayman to Chicago from £200️ (GCM-CHI)

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Latest Flight Deals from Grand Cayman to Chicago

Book one-way or return flights from Grand Cayman to Chicago from as little as £200. 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 Grand Cayman to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Grand Cayman to Chicago. 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 Grand Cayman to Chicago

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

Cayman Airways

From £200

Jetblue Airways

From £218

WestJet

From £238

United Airlines

From £245

Air Canada

From £253

American Airlines

From £270

Delta Air Lines

From £302

Southwest Airlines

From £338

ANA airlines

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Alternative Routes from Grand Cayman to Chicago

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

Cheapest
GCM
09:10
14h 21m
1 transfer
MDW
23:31
Owen Roberts International Airport - Midway International Airport
Sat, Apr 27Cayman Airways
£200
GCM
09:30
25h 17m
2 transfer
ORD
10:47
Owen Roberts International Airport - O'Hare International Airport
Mon, May 6Cayman Airways
£209
GCM
09:30
25h 17m
2 transfer
ORD
10:47
Owen Roberts International Airport - O'Hare International Airport
Mon, May 6Cayman Airways
£209
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How do I find the cheapest flights?

When are flight tickets from Grand Cayman (GCM) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Grand Cayman to Chicago 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 Grand Cayman (GCM) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around £579.
How long is the flight from Grand Cayman (GCM) to Chicago (CHI)?
It takes about 4 hours 10 minutes to fly from Grand Cayman (GCM) to Chicago (CHI).
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
What are the most popular airlines that fly from Grand Cayman (GCM) to Chicago (CHI)?
Airlines with flights from Grand Cayman (GCM) to Chicago (CHI): United Airlines.
What's the most popular airline for direct flights from Grand Cayman (GCM) to Chicago (CHI)?
United Airlines operates 1 direct flights from Grand Cayman (GCM) to Chicago (CHI).
How many airports in Chicago (CHI)?
There are 5 airport(s) in Chicago (CHI): Chicago Du Page County Airport, Midway International Airport, O'Hare International Airport, Chicago Palwaukee Airport and Chicago Rockford International Airport.

How to find a cheap flight from Grand Cayman to Chicago

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 Grand Cayman to Chicago. 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 Grand Cayman to Chicago

Cheapest direct flight price	£200
Cheapest return ticket price	£473
Cheapest month	January
Peak season for travel	July
Flight distance	2,580.07km
Average flight time	4 hours 10 minutes
Popular airline	United Airlines