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  1. Flights
  2. United States
  3. Key West, FL
  4. Chicago - Key West, FL

Cheap Flights from Chicago (CHI) to Key West, FL (EYW)

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Discover the cheapest flights from Chicago to Key West, FL
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Fri, May 1 - Thu, May 7
American Airlines
American Airlines1 stop
CHI - EYW
American Airlines
American AirlinesDirect
EYW - CHI
240$
239$
Prime price per passenger
Tue, Jun 2 - Wed, Jun 10
American Airlines
American AirlinesDirect
CHI - EYW
American Airlines
American AirlinesDirect
EYW - CHI
309$
Prime price per passenger
Tue, May 12 - Wed, May 20
American Airlines
American AirlinesDirect
CHI - EYW
American Airlines
American AirlinesDirect
EYW - CHI
315$
309$
Prime price per passenger
Wed, Jun 24 - Wed, Jul 1
American Airlines
American Airlines1 stop
CHI - EYW
American Airlines
American AirlinesDirect
EYW - CHI
319$
Prime price per passenger
Sun, May 24 - Sun, May 31
American Airlines
American AirlinesDirect
CHI - EYW
American Airlines
American Airlines1 stop
EYW - CHI
325$
319$
Prime price per passenger
Sat, Jun 13 - Fri, Jun 19
American Airlines
American Airlines1 stop
CHI - EYW
American Airlines
American Airlines1 stop
EYW - CHI
332$
329$
Prime price per passenger
Mon, Apr 27
Spirit Airlines
Spirit Airlines1 stop
CHI - EYW
118$
111$
Prime price per passenger
Sat, May 9
American Airlines
American AirlinesDirect
CHI - EYW
157$
155$
Prime price per passenger
Sun, Jun 21
American Airlines
American AirlinesDirect
CHI - EYW
190$
189$
Prime price per passenger
Tue, Jun 23
American Airlines
American AirlinesDirect
CHI - EYW
191$
189$
Prime price per passenger
Wed, Jun 10
American Airlines
American AirlinesDirect
CHI - EYW
193$
189$
Prime price per passenger
Sat, May 23
American Airlines
American Airlines1 stop
CHI - EYW
205$
199$
Prime price per passenger
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 April. 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.
Filter by
week: Apr 27 - May 3
Flights from just $294
$294
$465
$391
$422
$396
$377
$452
$451
$493
$621
$749
$902
AprilMayJuneJuly
Flying Time3 h and 26 mWhen flying from Chicago to Key West, FL, this can take around 3 h and 26 m in flying time, however this flight duration can vary due to other factors
Cheapest flight$111The best price for flights from Chicago to Key West, FL offered by eDreams, which have been found by our customers in the last 3 days
Origin airportsO'hare International Airport, Midway International AirportFor flights from Chicago to Key West, FL
Destination airportKey West International AirportFor the route from Chicago to Key West, FL
Peak seasonMarchMarch is the busiest time to fly from Chicago to Key West, FL according to search data results from our customers
Airlines operating this routeAmerican AirlinesAirline(s) that fly from Chicago to Key West, FL
One-way average Price$387A flight from Chicago to Key West, FL at eDreams will cost around $387, this being based on prices of the previous 6 months of data
Best time to bookMarchDecember is one of the most frequent times to fly to Key West, FL from Chicago according to real data from our customers
Distance: 1241 miles
Chicago airports
O'hare International Airport (ORD)How far from city center: 14 miles
Midway Airport (MDW)How far from city center: 4 miles
Key West, FL airports
Key West (EYW)How far from city center: 1 miles

Are you planning to travel to Key West, FL for vacations, business or family visits? eDreams offers you the cheapest flights and best deals departing from Chicago. With our fast search engine you will get a large selection of airfares from standard and low cost airlines worldwide and easily book your tickets for this route. If you are flexible we help you identify the cheapest day to fly to Key West, FL and if you need to leave soon you can check our most convenient last minute fares. Read all the useful information about your next destination and proceed to the reservation, indicating your flight dates and completing your travel booking with hotels and car rental!

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

What are the benefits of booking flexible flight tickets?
Using the flexible flight ticket, you're guaranteed a refund or a rebooking option (without fees) in case of flight cancellations when travelling to United States. At eDreams have you covered!
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 $387. However, this price depends on many other factors such as seasonality or how far in advance the route has been booked.
For flights from Chicago to Key West, FL, how can I find the cheapest price?
The cheapest price for a flight from Chicago to Key West, FL is $111. At eDreams 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 booking, when is the best time to get the best prices for flights from Chicago to Key West, FL?
The most popular months to book a trip from Chicago to Key West, FL are October, September and April, 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 visit Key West, FL depends on lots of personal preferences, especially the price. Regarding popularity, December is the best month to fly to Key West, FL from Chicago in terms of searches from our customers, followed by October and November. If you prefer to avoid the busy season and get away from the crowds June, July and August are the months with fewer searches for Chicago - Key West, FL.
How long does the flight from Chicago to Key West, FL take?
Flight length from Chicago to Key West, FL is around 3 h and 26 m on average, at an average distance of 1,241.56 mi, for flights for the route (which may have 1 or more stops in other cities in between).

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