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Flights from Chicago to Key West

Cheap flight deals from Chicago to Key West

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

  • Round-trip
  • One way

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

Flight Info | Chicago to Key West

Cheapest one-way flight price AED 378
Cheapest return ticket price AED 2,949
Off-season for travel April
Peak season for travel June
Flight distance 2,001.04 km
Average flight time 3 hours 11 minutes
Popular airline Delta Air Lines

When is the cheapest time to fly from Chicago to Key West?

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

Cheapest flights
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  • 8 15
  • 15 22
  • 22 29

  • Jul

    29 6
  • 6 13
  • 13 20
  • 20 27

  • Aug

    27 3
  • 3 10
  • 10 17
  • 17 24
  • 24 31
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • 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 lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Key West (EYW) cost?

    According to Trip.com's data, the lowest price is around AED 1,821.

  • How long does it take to fly from Chicago (CHI) to Key West (EYW)?

    It takes about 3 hours 11 minutes to fly from Chicago (CHI) to Key West (EYW).

  • 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): American Airlines.

  • How many airports are there in Key West (EYW)?

    There are 1 airport(s) near Key West (EYW): Key West International Airport.

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.
1
Being flexible with your dates to get the cheapest Chicago to Key West ticket.
Tap "Date" on flight search bar to scan through the calender for Chicago to Key West airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Sat, Jun 21 at AED 379 for one-way flights.
2
Compare cheap Chicago to Key West flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Chicago to Key West. The cheapest airline operating is Frontier Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your Chicago to Key West route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Chicago to Key West flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
5
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
6
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Chicago to Key West to get exclusive deals for you.

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