Cheap Flights from Chicago to Key West from CAD 125️ 2024

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Find Chicago to Key West flights starting at CAD 125.

Book one-way or return flights from Chicago to Key West from as little as CAD 125. 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 Key West? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Chicago to Key West. 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 Cheapest Airlines Flying from Chicago to Key West

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

American Airlines

From CAD 125

United Airlines

From CAD 174

Spirit Airlines

From CAD 184

Frontier Airlines

From CAD 205

Delta Air Lines

From CAD 245

Southwest Airlines

From CAD 327

Allegiant Air

From CAD 446

ANA airlines

Find more flights and airlines

Alternative Routes for Chicago to Key West Flights

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

Cheapest
ORD
08:25
3h 14m
Direct
EYW
12:39
O'Hare International Airport - Key West International Airport
Tue, Apr 30American Airlines
CAD 125
MDW
06:20
8h 5m
1 transfer
EYW
15:25
Midway International Airport - Key West International Airport
Wed, Jun 26Frontier Airlines
CAD 206
RFD
08:36
9h 59m
1 transfer
EYW
19:35
Chicago Rockford International Airport - Key West International Airport
Fri, May 24Allegiant Air
CAD 446
RFD
08:36
9h 59m
1 transfer
EYW
19:35
Chicago Rockford International Airport - Key West International Airport
Fri, May 24Allegiant Air
CAD 446
Find More Flights

How do I find the cheapest flights?

When are flight tickets from Chicago (CHI) to Key West (EYW) the cheapest?
Airlines adjust prices for flights from Chicago to Key West 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 Key West (EYW) cost?
According to Trip.com's data, the lowest price is around CAD 689.
How long is the flight from Chicago (CHI) to Key West (EYW)?
It takes about 3 hours 9 minutes to fly from Chicago (CHI) to Key West (EYW).
What is the transportation method from the main airport to downtown in Key West?
- The distance from Key West International Airport to downtown is about 2km, by taxi about 20 minutes.
What are the most popular airlines that fly from Chicago (CHI) to Key West (EYW)?
Airlines with flights from Chicago (CHI) to Key West (EYW): United Airlines and American Airlines.
What's the most popular airline for direct flights from Chicago (CHI) to Key West (EYW)?
American Airlines operates 4 direct flights from Chicago (CHI) to Key West (EYW).
How many airports in Key West (EYW)?
There are 2 airport(s) in Key West (EYW): Key West International Airport and Key West Nas.

How to find a cheap flight from Chicago to Key West

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 Key West. 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 for Chicago to Key West Flights

Cheapest direct flight price	CAD 125
Cheapest return ticket price	CAD 414
Cheapest month	April
Peak season for travel	July
Flight distance	2,001.04km
Average flight time	3 hours 9 minutes
Popular airline	American Airlines