S$149 Cheap Flights from Chicago to Key West

View S$149 flight on Tue, 4 MarOpens in a new window

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

Prices were available within the past 7 days and start at S$149 for one-way flights and S$297 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$297 Return, found 2 days ago
S$297
Return
found 2 days ago
Select Delta flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$297 found 2 days ago
Delta
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$327 Return, found 2 days ago
S$327
Return
found 2 days ago
Select Delta flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$327 found 2 days ago
Delta
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$339 Return, found 2 days ago
S$339
Return
found 2 days ago
Select Delta flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$339 found 2 days ago
United
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$356 Return, found 2 days ago
S$356
Return
found 2 days ago
Select United flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$356 found 2 days ago
Delta
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$370 Return, found 2 days ago
S$370
Return
found 2 days ago
Select Delta flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$370 found 2 days ago
Delta
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$422 Return, found 2 days ago
S$422
Return
found 2 days ago
Select Delta flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$422 found 2 days ago
United
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$431 Return, found 2 days ago
S$431
Return
found 2 days ago
Select United flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$431 found 2 days ago
Delta
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$436 Return, found 2 days ago
S$436
Return
found 2 days ago
Select Delta flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$436 found 2 days ago
United
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$452 Return, found 2 days ago
S$452
Return
found 2 days ago
Select United flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$452 found 2 days ago
American Airlines
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$464 Return, found 2 days ago
S$464
Return
found 2 days ago
Select American Airlines flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$464 found 2 days ago
Delta
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$464 Return, found 2 days ago
S$464
Return
found 2 days ago
Select Delta flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$464 found 2 days ago
Delta
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$466 Return, found 2 days ago
S$466
Return
found 2 days ago
Select Delta flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$466 found 2 days ago
Delta
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$477 Return, found 2 days ago
S$477
Return
found 2 days ago
Select Delta flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$477 found 2 days ago
Delta
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$479 Return, found 2 days ago
S$479
Return
found 2 days ago
Select Delta flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$479 found 2 days ago
American Airlines
Tue, 4 Mar - Tue, 11 Mar
ORD
Chicago
EYW
Key West
S$493 Return, found 2 days ago
S$493
Return
found 2 days ago
Select American Airlines flight, departing Tue, 4 Mar from Chicago to Key West, returning Tue, 11 Mar, priced at S$493 found 2 days ago
Chicago to Key West route information
Origin airport
O'Hare Intl.
Destination airport
Key West Intl.
Return price
S$297
Distance
2006 km

Perfect flights from Chicago to Key West

Your Journey from Chicago to Key West

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to Key West caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, United, American Airlines. Our selection of flights from O'Hare Intl. to Key West Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to Key West Flights

Experience the joy of finding cheap flights from O'Hare Intl. to Key West Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$149 and roundtrip prices from S$297*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to Key West with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Key West

Picture yourself stepping off the plane in Key West and immersing yourself in the unique atmosphere of Key West. From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to Key West Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to Key West.
 

Beyond the Flight – Exploring Key West

With Expedia, your adventure extends beyond the flight. Explore Key West at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to Key West with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to Key West with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

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 S$297. 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.
Chicago Airports

Chicago

Midway Intl. to Key West
S$296.90
*Available to Expedia members.