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  3. Key West, FL
  4. Chicago - Key West, FL

Cheap Flights from Chicago to Key West, FL - Compare and Book on Opodo

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Cheapest time to fly from Chicago to Key West, FL

If you’re planning to fly this route soon, keep in mind that the lowest fares are usually available at the end of June. Take advantage of this per
week: 22 June - 28 June
Flights from just $455
$455
$550
$550
JuneJulyAugustSeptember
Distance: 1998 kms
Chicago airports
Key West, FL airports

Get the Best Deals on Flights from Chicago to Key West, FL

Discover the best last-minute airfares and cheap prices from Chicago to Key West, FL with Opodo Australia. Avoid overspending on flight tickets and start planning your perfect getaway. Opodo offers a hassle-free booking experience, providing access to top airline carriers and the most competitive prices.


Find the best flights that fit your needs

When do you want to depart from Chicago? Adjust your travel dates and explore a wide range of options to Key West, FL. With Opodo, you can find the perfect flight from our extensive selection, ensuring a seamless and enjoyable trip. Compare prices, flight durations, and amenities to choose the best option that suits your needs.


Book all in one place

But wait, there's more! Enhance your travel experience by booking a hotel and renting a car along with your flight. It's easier and often cheaper to book everything together. Choose the best offer from Chicago to Key West, FL and get ready for an incredible journey. Enjoy your holiday, and remember to fasten your seatbelt. We’re ready for takeoff!

Frequently asked questions about flights from Chicago to Key West, FL

How long does the flight take to go from Chicago to Key West, FL?
The total flight time between Chicago and Key West, FL is of around 4 h and 30 m on average, considering an average distance of 1,998.09 km, for both direct and indirect flights for the route (which may have 1 or more stops in other cities in between).
On average, how much is the price of a flight from Chicago to Key West, FL?
When you fly from Chicago to Key West, FL the average price is $579. However, this price depends on many other factors such as seasonality or how far in advance the route has been booked.
How can I find cheap flights from Chicago to Key West, FL at Opodo?
At Opodo we use different machine learned based methodologies to find our costumers the cheapest flight available from Chicago to Key West, FL. Considering airline combinations, stopovers and direct flights as well as different criteria for inbound and outbound journeys, our search engine works to provides always the best price with the best conditions.
When is the best time to book a flight from Chicago to Key West, FL?
The most popular months to book a trip from Chicago to Key West, FL are December, November and July, based on the searches of our customers.
When is the best time to travel from Chicago to Key West, FL?
The best time of the year to go to Key West, FL when flying from Chicago depends on several preference factors like climate, seasonality and, of course, price. When it comes to popularity, June is the top 1º month to fly to Key West, FL from Chicago in terms of searches from our customer, followed by July and August. If you prefer to avoid high peaks of turism, however, and escape a crowded period, September, January and May are the months with less volume of searchs for the route Chicago - Key West, FL.
How is the weather in Key West, FL compared to Chicago?
While in Chicago temperatures can reach an average of 22º ºC in summer, Key West, FL's temperatures can rise to 29º ºC during the hot season. In winter, however, weather data show around 21º ºC in Key West, FL, compared to the -3º ºC average in Chicago.

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