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Flights from Chicago to Key West, FL

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Discover the cheapest flights from Chicago to Key West, FL
The prices shown on this page were available within the last 20 days for the specified periods and should not be considered the final price offered. Please note that availability and prices are subject to change.

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 November. Take advantage of this period to save on your flight tickets and make the most of your trip. Please note that prices may change after your search.
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week: 23 Nov - 29 Nov
£268
November
Distance: 1,242 mi
Chicago airports
O'hare International Airport (ORD)How far from city centre: 13 mi
Key West, FL airports

Book your Chicago to Key West, FL flight

Search direct and connecting flights from Chicago to Key West, FL (United States) with Opodo. When your results appear, sort them by timing or fare and book whichever option fits your plans best.

The cheapest fare booked on this route in recent days was £313, although the price you're shown will vary with your travel dates and departure times.

Flying non-stop from Chicago to Key West, FL takes roughly 3 h and 19 m, whereas journeys with a layover will take longer.

Airports and airlines on the Chicago–Key West, FL route

Plan your trip with confidence by checking the relevant airports and comparing the airlines that fly this route.

  • Departure airport: O'hare International Airport (ORD)

The weather in Key West, FL

The best time to go may come down to the kind of weather you most enjoy. In Key West, FL, temperatures average around 32ºC in the warmest months and roughly 19ºC in the coldest. Bear this in mind when deciding what to pack and planning time outdoors.

  • Highs: up to 32ºC
  • Lows: down to 18ºC
  • Hottest month: August
  • Coldest month: January
  • Driest month: February
  • Wettest month: September

Tips for cheaper flights from Chicago to Key West, FL

A few ways to bring down the cost of your flight from Chicago to Key West, FL:

  • Flexible dates: check fares across two or three departure days. Going a day earlier or later can make a real difference to what you pay.
  • Baggage allowance: see what's included in each fare before booking, so you're not stung by unexpected charges at the airport.
  • Airports on your route: double-check which airports you'll fly from and into, particularly if the city has more than one. It makes it easier to plan transfers and work out the full cost of getting around.

After a bigger saving? Book a Flight + Hotel package to combine the two in a single booking and unlock exclusive discounts on your stay in Key West, FL. Adding car hire to the same booking can save you money too.

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

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 £286. 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?
The cheapest price for a flight from Chicago to Key West, FL is 313 £. At Opodo we use different machine learned based methodologies to find our costumers the best option available, considering airline combinations, stopovers and direct flights as well as different criteria for inbound and outbound journeys.
When is the best time to book a flight from Chicago to Key West, FL?
The most popular months to book a flight from Chicago to Key West, FL are December, March and October, 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, March is the top 1º month to fly to Key West, FL from Chicago in terms of searches from our customer, followed by February and April. If you prefer to avoid high peaks of turism, however, and escape a crowded period, October, June and January are the months with less volume of searchs for the route Chicago - 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 5 h and 27 m on average, considering an average distance of 1,241.56 mi, for both direct and indirect flights for the route (which may have 1 or more stops in other cities in between).
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 can experience temperatures up to 29º ºC during the hot season. In winter, however, the weather shows around 21º ºC in Key West, FL, compared to the -3º ºC average in Chicago.

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