
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 €128 for one-way flights and €290 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, 30 Aug - Fri, 5 Sep
ORD
Chicago
EYW
Key West
€290 Return, found 1 day ago
€290
Return
found 1 day ago

Sat, 30 Aug - Fri, 5 Sep
ORD
Chicago
EYW
Key West
€307 Return, found 1 day ago
€307
Return
found 1 day ago

Sat, 30 Aug - Fri, 5 Sep
ORD
Chicago
EYW
Key West
€317 Return, found 1 day ago
€317
Return
found 1 day ago

Sat, 30 Aug - Fri, 5 Sep
ORD
Chicago
EYW
Key West
€329 Return, found 1 day ago
€329
Return
found 1 day ago

Sat, 30 Aug - Fri, 5 Sep
ORD
Chicago
EYW
Key West
€333 Return, found 1 day ago
€333
Return
found 1 day ago

Sat, 30 Aug - Fri, 5 Sep
ORD
Chicago
EYW
Key West
€337 Return, found 1 day ago
€337
Return
found 1 day ago

Sat, 30 Aug - Fri, 5 Sep
ORD
Chicago
EYW
Key West
€347 Return, found 1 day ago
€347
Return
found 1 day ago

Sat, 30 Aug - Fri, 5 Sep
ORD
Chicago
EYW
Key West
€356 Return, found 1 day ago
€356
Return
found 1 day ago

Sat, 30 Aug - Fri, 5 Sep
ORD
Chicago
EYW
Key West
€359 Return, found 1 day ago
€359
Return
found 1 day ago

Sat, 30 Aug - Fri, 5 Sep
ORD
Chicago
EYW
Key West
€360 Return, found 1 day ago
€360
Return
found 1 day ago
Find the cheapest month to fly from Chicago (ORD) to Key West (EYW)
November is typically the cheapest month to fly
From €163 - €519 per traveller.
Graph displaying average flight prices per month
Origin airport | O'Hare Intl. |
Destination airport | Key West Intl. |
Return price | €290 |
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 €128 and roundtrip prices from €290. 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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