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Flights from Chicago to Key West Starting at £70

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip

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

Find the best time to fly from Chicago to Key West

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying 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 £70
United Airlines
From £101
Frontier Airlines
From £119
Spirit Airlines
From £131
Southwest Airlines
From £190
Delta Air Lines
From £197
Jetblue Airways
From £416
ANA airlines

Find more flights and airlines

Alternative Routes from Chicago to Key West

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Chicago to Key West.

  • Cheapest
    American Airlines
    ORD
    08:25
    3h 14m
    Direct
    EYW
    12:39
    O'Hare International Airport - Key West International Airport
    Tue, Apr 16American Airlines
    £71
  • Frontier Airlines
    MDW
    05:45
    12h 0m
    2 transfer
    EYW
    18:45
    Midway International Airport - Key West International Airport
    Sat, May 4Frontier Airlines
    £126
  • Frontier Airlines
    MDW
    05:45
    12h 0m
    2 transfer
    EYW
    18:45
    Midway International Airport - Key West International Airport
    Sat, May 4Frontier Airlines
    £126
    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 £450.
  • How long is the flight from Chicago (CHI) to Key West (EYW)?

    It takes about 3 hours 10 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.

Flight Information from Chicago to Key West

Cheapest direct flight price

£70

Cheapest return ticket price

£208

Cheapest month

April

Peak season for travel

June