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Cheap Flights from Chicago to Key West $429.19

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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 : Is price more important than specific travel days for you?
Answer : The cheapest day to fly in May is Sunday. Flexibility is paramount when booking travel plans in order to keep travel costs down.

Question : Over the coming months, which airline is getting their passengers to Key West International Airport (EYW) round-trip the cheapest?
Answer : Ticket costs are hitting as high as $760 over the next three months when flying to EYW from MDW. Check out Delta Air Lines, as they have been booking customers at just $397.

Question : Should you take that vacation to Key West in the next 30 days?
Answer : As of Apr 17th, the cheapest day to fly from Chicago to Key West is May 16th. Tickets are currently being sold for $416, which is 27% below the average price for this route.

Question : Is the price you found a good deal?
Answer : Ranging from $397 to $760, prices for MDW to EYW change less than most routes in the United States. The further out you book a route, the more likely you are to save.

Question : Is this route your best bet for getting to Key West with minimal delays?
Answer : MDW to EYW currently scores 4 out of a possible 5 stars in promptness. This score combines both the number of delayed flights and total delay minutes. With 4 stars, you should feel confident in getting to Key West on time.

Question : Is Chicago Midway International Airport (MDW) the cheapest airport for getting to Key West International Airport (EYW)?
Answer : O'Hare International Airport is just 16 miles away, and, on average, flights are 21% cheaper for the next few months. Save a few bucks and put it toward your next trip.

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 about one week on average.