S$234 Cheap Flights from Chicago to Key West

View S$234 flight on Tue, 19 Aug, 2025Opens in a new window

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

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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$234 for one-way flights and S$343 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 19 Aug - Tue, 26 Aug
ORD
Chicago
EYW
Key West
S$343 Return, found 1 day ago
S$343
Return
found 1 day ago
Select Delta flight, departing Tue, 19 Aug from Chicago to Key West, returning Tue, 26 Aug, priced at S$343 found 1 day ago
Delta
Wed, 20 Aug - Wed, 27 Aug
ORD
Chicago
EYW
Key West
S$402 Return, found 2 days ago
S$402
Return
found 2 days ago
Select Delta flight, departing Wed, 20 Aug from Chicago to Key West, returning Wed, 27 Aug, priced at S$402 found 2 days ago
Delta
Tue, 19 Aug - Tue, 26 Aug
ORD
Chicago
EYW
Key West
S$409 Return, found 1 day ago
S$409
Return
found 1 day ago
Select Delta flight, departing Tue, 19 Aug from Chicago to Key West, returning Tue, 26 Aug, priced at S$409 found 1 day ago
Delta
Mon, 18 Aug - Mon, 25 Aug
ORD
Chicago
EYW
Key West
S$467 Return, found 3 days ago
S$467
Return
found 3 days ago
Select Delta flight, departing Mon, 18 Aug from Chicago to Key West, returning Mon, 25 Aug, priced at S$467 found 3 days ago
Delta
Wed, 20 Aug - Wed, 27 Aug
ORD
Chicago
EYW
Key West
S$490 Return, found 2 days ago
S$490
Return
found 2 days ago
Select Delta flight, departing Wed, 20 Aug from Chicago to Key West, returning Wed, 27 Aug, priced at S$490 found 2 days ago
American Airlines
Tue, 19 Aug - Tue, 26 Aug
ORD
Chicago
EYW
Key West
S$514 Return, found 1 day ago
S$514
Return
found 1 day ago
Select American Airlines flight, departing Tue, 19 Aug from Chicago to Key West, returning Tue, 26 Aug, priced at S$514 found 1 day ago
Delta
Fri, 8 Aug - Wed, 13 Aug
ORD
Chicago
EYW
Key West
S$516 Return, found 5 days ago
S$516
Return
found 5 days ago
Select Delta flight, departing Fri, 8 Aug from Chicago to Key West, returning Wed, 13 Aug, priced at S$516 found 5 days ago
Delta
Tue, 19 Aug - Tue, 26 Aug
ORD
Chicago
EYW
Key West
S$532 Return, found 1 day ago
S$532
Return
found 1 day ago
Select Delta flight, departing Tue, 19 Aug from Chicago to Key West, returning Tue, 26 Aug, priced at S$532 found 1 day ago
American Airlines
Tue, 19 Aug - Tue, 26 Aug
ORD
Chicago
EYW
Key West
S$548 Return, found 1 day ago
S$548
Return
found 1 day ago
Select American Airlines flight, departing Tue, 19 Aug from Chicago to Key West, returning Tue, 26 Aug, priced at S$548 found 1 day ago
United
Wed, 20 Aug - Wed, 27 Aug
ORD
Chicago
EYW
Key West
S$598 Return, found 2 days ago
S$598
Return
found 2 days ago
Select United flight, departing Wed, 20 Aug from Chicago to Key West, returning Wed, 27 Aug, priced at S$598 found 2 days ago

Find the cheapest month to fly from Chicago (ORD) to Key West (EYW)

November is typically the cheapest month to fly

From S$241 - S$846 per traveller.

Graph displaying average flight prices per month

Chicago to Key West route information
Origin airport
O'Hare Intl.
Destination airport
Key West Intl.
Airlines serving
American Airlines, Delta, United
Return price
S$343
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, American Airlines, United. 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$234 and roundtrip prices from S$343*.
 

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 . 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$343. 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

Chicago Airports

Chicago

Midway Intl. to Key West
S$342.90
*Available to Expedia members.