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

Popular airlines from Chicago Midway Airport (MDW) to Key West Intl. Airport (EYW)

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Frequently asked questions

Is it cheaper to buy a plane ticket from Midway Airport to Key West Intl. Airport last minute?
When it comes to booking your flights, being prepared pays dividends. While it's possible to score a deal on a Midway Airport to Key West Intl. Airport flight at the last minute, tickets usually don't get cheaper as the date of departure nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to book a domestic flight is between 28 – 35 days ahead. For international journeys it's three to four months.
Can I change the date of my flight from Midway Airport to Key West Intl. Airport (EYW)?
Quickly and easily make changes to your Midway Intl. Airport (MDW) to Key West Intl. Airport (EYW) ticket via the Expedia Trips portal. Before you amend times or dates, review the rules and conditions in your itinerary to find out what the carrier will let you do and if charges apply. Some carriers have a change fee per person, plus any difference in ticket prices. But if you booked in the last 24 hours, you may be able to cancel for free and book new flights. You can also check out our Customer Service portal to find the answers to your questions and to chat with our Virtual Agent.

Travel information

Origin airport
Midway Intl.
Destination airport
Key West Intl.
Distance
1982 km

Book with confidence

Chicago to Key West Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Chicago to Key West offer the perfect respite. Not only does exploring Key West provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Chicago to Key West may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Key West are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Key West more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Key West is now!

Chicago to Key West Flights

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