Trip.com
>
Flights
>
Flights to United States
>
Flights to Illinois
>
Flights to Chicago
>
Flights from Key West to Chicago

Cheap flight deals from Key West to Chicago

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.

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

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

Cheapest flights
From price
Search
  • 6 13
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
  • 8 15
  • 15 22
  • 22 29
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 Key West (EYW) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Key West to Chicago 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 Key West (EYW) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around AED 1,635.

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

    It takes about 3 hours 30 minutes to fly from Key West (EYW) 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 25 km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14 km, by taxi about 30 minutes.

  • What are the most popular airlines that fly from Key West (EYW) to Chicago (CHI)?

    Airlines with flights from Key West (EYW) to Chicago (CHI): United Airlines, Air New Zealand, Qatar Airways and American Airlines.

  • What's the most popular airline for non-stop flights from Key West (EYW) to Chicago (CHI)?

    American Airlines operates 4 non-stop flights from Key West (EYW) to Chicago (CHI).

  • How many airports are there in Chicago (CHI)?

How to find a cheap flight from Key West 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 Key West to Chicago. Book your flights at the right time and save more.
1
Being flexible with your dates to get the cheapest Key West to Chicago ticket.
Tap "Date" on flight search bar to scan through the calender for Key West to Chicago airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Fri, Apr 25 at AED 941 for one-way flights.
2
Compare cheap Key West to Chicago 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 Key West to Chicago. The cheapest airline operating is United Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your Key West to Chicago route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Key West to Chicago 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 Key West to Chicago to get exclusive deals for you.

Flight Info | Key West to Chicago

Cheapest one-way flight price AED 445
Cheapest return ticket price AED 1,196
Off-season for travel March
Peak season for travel January
Flight distance 2,001.04 km
Average flight time 3 hours 30 minutes
Popular airline Silver Airways

More Travel Options

  • Top Routes from Key West
  • Top Routes to Chicago
  • Trending Airlines