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Cheap Flights from Chicago to Key West $465.56

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Cheapest Flights from Chicago to Key West (MDW to EYW)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Chicago to Key West (MDW to EYW)

Question : Interested in traveling in the next 30 days and want to get the lowest fare?
Answer : As of January 16th, the best day for deals to Key West (EYW) from Chicago (MDW) is February 8th. Bookings have been made roughly 25% below the average price for this route.

Question : Have you considered flying out of an airport besides Chicago Midway International Airport (MDW)?
Answer : Luckily for you, there is another airport nearby. O'Hare International Airport (ORD) is 16 miles away, and over the next few months, flights are 11% cheaper than those from Chicago Midway International Airport.

Question : Do travelers from Chicago typically stay in Key West for very long?
Answer : Over the next two months, passengers from MDW to EYW are planning on staying for six days on average.

Question : Can you cut down on flight costs by changing the day of the week you travel to Key West?
Answer : In February, Saturday is your cheapest day to fly. Flexibility is paramount when booking travel plans in order to keep costs down.

Question : How often is the price changing when booking a trip from Chicago Midway International Airport (MDW) to Key West International Airport (EYW)?
Answer : Prices for MDW to EYW do change much more than most. However, the sooner you book, the better price you tend to get.

Question : Is this route your best bet for getting to Key West with minimal delays?
Answer : The best way to measure a flight's promptness combines both on-time percentage and total delay minutes. MDW to EYW currently has 3.6 stars out of 5, an average score at best.