Cheap Flights from O'Hare Intl. to Key West Intl.

Prices were available within the past 7 days and starts at $166 for one-way flights and $296 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Flights from Chicago to Key West: Reviews from verified customers

Mar 11, 2020

Good stuff

Mar 5, 2020

Good service

Jun 12, 2018

Everything a cetcthey kept us on plane in return flight one hour while they waited for an attendant to arrive from another plane . Should have left us in the airport until ready for us

May 10, 2018

Smoothest landing I've ever had in Key West airport

Mar 2, 2018

Need more legroom. Person in front of me was almost in my lap.

Feb 17, 2018

Good job

Jan 28, 2018

Direct to Key West was the best no changing planes

Feb 12, 2017

Nice direct flight

Flight from Chicago to Key West route information

Origin Airport O'Hare Intl.
Destination Airport Key West Intl.
Airlines Serving American Airlines, Delta, JetBlue Airways, United
Flight Price $295
Distance 1,254 mi

Chicago to Key West (ORD-EYW) route frequently asked questions

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 ORD to EYW 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 flexbily many prefers to purchase one-way tickets with options to take different airlines. One way ticket to Key West is $166 now!