
Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)
- American Airlines
American Airlines
- Delta
Delta
- United
United
- Spirit Airlines
Spirit Airlines
- JetBlue Airways
JetBlue Airways
- Plan, book, fly with confidence
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Cheap flights from Chicago to Key West (ORD-EYW)
Prices were available within the past 7 days and start at €143 for one-way flights and €316 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, 7 Sep - Mon, 15 Sep
ORD
Chicago
EYW
Key West
€316 Return, found 3 days ago
€316
Return
found 3 days ago

Sun, 7 Sep - Mon, 15 Sep
ORD
Chicago
EYW
Key West
€337 Return, found 3 days ago
€337
Return
found 3 days ago

Sun, 7 Sep - Mon, 15 Sep
ORD
Chicago
EYW
Key West
€349 Return, found 3 days ago
€349
Return
found 3 days ago

Sun, 7 Sep - Mon, 15 Sep
ORD
Chicago
EYW
Key West
€355 Return, found 3 days ago
€355
Return
found 3 days ago

Sun, 7 Sep - Mon, 15 Sep
ORD
Chicago
EYW
Key West
€372 Return, found 3 days ago
€372
Return
found 3 days ago

Sun, 7 Sep - Mon, 15 Sep
ORD
Chicago
EYW
Key West
€377 Return, found 3 days ago
€377
Return
found 3 days ago

Sun, 7 Sep - Mon, 15 Sep
ORD
Chicago
EYW
Key West
€383 Return, found 3 days ago
€383
Return
found 3 days ago

Sun, 7 Sep - Mon, 15 Sep
ORD
Chicago
EYW
Key West
€392 Return, found 3 days ago
€392
Return
found 3 days ago

Sun, 7 Sep - Mon, 15 Sep
ORD
Chicago
EYW
Key West
€394 Return, found 3 days ago
€394
Return
found 3 days ago

Sun, 7 Sep - Mon, 15 Sep
ORD
Chicago
EYW
Key West
€443 Return, found 3 days ago
€443
Return
found 3 days ago
Find the cheapest month to fly from Chicago (ORD) to Key West (EYW)
November is typically the cheapest month to fly
From €162 - €473 per traveller.
Graph displaying average flight prices per month
Origin airport | O'Hare Intl. |
Destination airport | Key West Intl. |
Return price | €316 |
Distance | 2006 km |
Perfect flights from Chicago to Key West
Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Chicago to Key West. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
Picture yourself strolling through the streets of , surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
Our flexible O'Hare Intl. to Key West Intl. ticket options cater to your travel preferences, with incredible one-way fares from €143 and roundtrip prices from €316. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Key West Intl. and explore and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your to travel arrangements today and embark on the journey of a lifetime in Key West.
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Top Routes from Chicago
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