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

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)

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Frequently asked questions

How long does it take to fly from ORD to Key West Intl. Airport?
American Airlines operates a direct flight setting off from ORD at 8:20AM and reaching Key West Intl. Airport at 12:34PM — a total flight time of 3 hours and 14 minutes. Lock in the seat that's right for you, bring a magazine to keep you busy and enjoy the ride.
Is it cheaper to buy a plane ticket from ORD to EYW last minute?
Being the spontaneous type is a wonderful way to travel, but it's not always the smartest method to pick up a cheap plane ticket. It's better to book your ORD to EYW trip in advance instead of waiting until the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. Save up that spontaneity for when you're exploring EYW!
What are the most popular departure times for flights from ORD to Key West Intl. Airport (EYW)?
For American Airlines flights from O'Hare Airport to EYW, the most popular departure times are between 8:00 AM - 9:00 AM. If you'd like to avoid any holdups, head out in the morning. This gives you a better chance to miss the air traffic that builds up as the day goes by.
Can I change the date of my flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport?
Quickly and easily make changes to your ORD to Key West Intl. Airport (EYW) trip through the Expedia Trips portal. Before you make any amendments, look over the rules in your itinerary to learn what you're able to do and if fees apply for changes. Some carriers charge a change fee per person, plus any difference in 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 browse our Customer Service portal for more advice and to chat with our Virtual Agent.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Key West Intl.
Distance
2006 km
Average flight time
4 hours 24 mins

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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