$256 Find Cheap Flights from Grand Cayman to Chicago

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Find cheap flights from Grand Cayman to Chicago starting at $256.

Book one-way or return flights from Grand Cayman to Chicago from as little as $256. 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.

Find cheap airlines flights 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 $256

Jetblue Airways

From $273

United Airlines

From $307

Air Canada

From $325

American Airlines

From $338

Delta Air Lines

From $378

WestJet

From $384

Southwest Airlines

From $423

ANA airlines

Find more flights and airlines

Find cheap flights from Grand Cayman to Chicago by different airports

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

Cheapest
GCM
11:30
7h 48m
1 transfer
MDW
19:18
Owen Roberts International Airport - Midway International Airport
Tue, Jun 25Cayman Airways
$256
GCM
09:30
25h 17m
2 transfer
ORD
10:47
Owen Roberts International Airport - O'Hare International Airport
Mon, May 6Cayman Airways
$262
GCM
09:30
25h 17m
2 transfer
ORD
10:47
Owen Roberts International Airport - O'Hare International Airport
Mon, May 6Cayman Airways
$262
Find More Flights

Frequently Asked Questions

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 departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much do flights from Grand Cayman (GCM) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around $806.
How long does it take to fly from Grand Cayman (GCM) to Chicago (CHI) and what is the distance?
It takes around 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. It takes about 40 minutes by taxi.
- The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.
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.

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

Grand Cayman to Chicago Flight Information

Cheapest nonstop flight price	$255
Cheapest round-trip ticket price	$592
Off-season for travel	January
Peak season for travel	November
Flight distance	2,580.07km
Average flight time	4 hours 10 minutes
Popular airline	United Airlines