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Cheap Flights from Chicago to Key West $431.52

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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 : What is the cheapest day to fly in the next four weeks?
Answer : As of November 28th, the best day for booking to Key West (EYW) from Chicago (MDW) is December 11th. Bookings have been made roughly 56% below the average price for this route.

Question : Is there another local airport that can get you to Key West?
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 13% cheaper than those from Chicago Midway International Airport.

Question : How long do most people stay in Key West when they fly in from Chicago?
Answer : Over the next two months, passengers from MDW to EYW are planning on staying for six days on average.

Question : Would you be willing to change your travel days if it saved you money?
Answer : The best day to fly on a budget this month is Saturday. Having flexibility in your travel plans means you can save, so be sure to plan ahead when possible.

Question : Who's offering the cheapest round-trip flight to Key West International Airport (EYW) over the coming months?
Answer : Delta Air Lines is your best bet for finding that coveted low fare.

Question : In terms of overall promptness, how does MDW to EYW rank compared to the rest of the world?
Answer : Using the combined on-time percentage and average delay breakdown, Chicago to Key West currently has a 3.6 out of a possible 5 star rating. A 3.6 rating means you should plan on being flexible with your arrival plans.