Cheap Flights Chicago to Key West (ORD-EYW)

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

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

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$561 Return, found 5 days ago
NZ$561
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$561 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$574 Return, found 5 days ago
NZ$574
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$574 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$580 Return, found 5 days ago
NZ$580
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$580 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$580 Return, found 5 days ago
NZ$580
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$580 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$587 Return, found 5 days ago
NZ$587
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$587 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$588 Return, found 5 days ago
NZ$588
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$588 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$594 Return, found 5 days ago
NZ$594
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$594 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$599 Return, found 5 days ago
NZ$599
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$599 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$600 Return, found 5 days ago
NZ$600
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$600 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$601 Return, found 5 days ago
NZ$601
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$601 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$608 Return, found 5 days ago
NZ$608
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$608 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$614 Return, found 5 days ago
NZ$614
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$614 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$615 Return, found 5 days ago
NZ$615
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$615 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$618 Return, found 5 days ago
NZ$618
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$618 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$620 Return, found 5 days ago
NZ$620
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$620 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$629 Return, found 5 days ago
NZ$629
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$629 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$636 Return, found 5 days ago
NZ$636
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$636 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$638 Return, found 5 days ago
NZ$638
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$638 found 5 days ago
American Airlines
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$644 Return, found 5 days ago
NZ$644
Return
found 5 days ago
Select American Airlines flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$644 found 5 days ago
Delta
Mon, 15 Sep. - Sat, 20 Sep.
ORD
Chicago
EYW
Key West
NZ$651 Return, found 5 days ago
NZ$651
Return
found 5 days ago
Select Delta flight, departing Mon, 15 Sep. from Chicago to Key West, returning Sat, 20 Sep., priced at NZ$651 found 5 days ago
Flight from Chicago to Key West route information
Origin airport
O'Hare Intl.
Destination airport
Key West Intl.
Return price
NZ$561
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 and roundtrip prices from NZ$561. 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.

Frequently asked questions

How much is a flight from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
Start packing your suitcase, because round-trip flights between O'Hare Intl. Airport (ORD) and Key West Intl. Airport (EYW) start from NZ$561. That's based on fares advertised within the last 7 days on Expedia for flights departing within the next year. Prices can change quickly, so book now to lock in the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Airport to Key West Intl. Airport?
This can differ between airlines, as each one has its own terms and conditions. Visit the Customer Service Portal, where there are easy-to-follow instructions on how to cancel online.
How do I find cheap flights from O'Hare Intl. Airport (ORD) to EYW that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for O'Hare Airport to EYW flights, you'll see a "no change fees" filter for you to select.
How far is the flight from O'Hare Airport to Key West Intl. Airport (EYW)?
You'll be soaring through the sky for a while, as the flight distance from Chicago to Key West is 2 000 kilometres. Put together a playlist of your favourite songs before you leave home to keep yourself entertained during the flight.
Which airlines fly direct from O'Hare Airport to EYW?
A popular option with many savvy travellers, American Airlines (AA) offers 21 flights every month from O'Hare Airport to Key West Intl. Airport (EYW). Pick the one that suits your travel plans and book your seat today.
Are O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW) flight tickets cheaper when they're purchased at the last minute?
It is possible to nab a fantastic last-minute deal from O'Hare Intl. Airport (ORD) to EYW, but it can also be hit-or-miss. As many airlines publish prices up to 12 months in advance, it's worth keeping an eye on fares early and being ready to pounce when you spot a bargain. Expedia compares air carrier prices and updates flight deals often, so you can rest assured you're always getting the latest offers.

Explore a world of travel with Expedia

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