Flights from Chicago to Key West Starting at NZD 234

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

  • Round-trip
  • One way

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

Cheapest flights
From price
Search
  • 16 23
  • 23 30

  • Apr

    30 6
  • 6 13
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
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.
United Airlines logo United Airlines

FAQ

  • 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 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 Chicago (CHI) to Key West (EYW) cost?

    According to Trip.com's data, the lowest price is around NZD 856.

  • How long does it take to fly from Chicago (CHI) to Key West (EYW) and what is the distance?

    It takes around 3 hours 14 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 2 km. It takes about 20 minutes by taxi.

  • 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): Air New Zealand, United Airlines and American Airlines.

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
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from Chicago to Key West

Cheapest nonstop flight price NZD 233
Cheapest round-trip ticket price NZD 547
Off-season for travel February
Peak season for travel June
Flight distance 2,001.04 km
Average flight time 3 hours 14 minutes
Popular airline United Airlines

Popular Flights

  • Top Routes from Chicago
  • Top Routes to Key West
  • More flight options