S$274 Cheap Flights from Chicago to Key West

View S$274 flight on Wed, 21 May, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 40% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

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

Prices were available within the past 7 days and start at S$274 for one-way flights and S$356 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 21 May - Wed, 28 May
ORD
Chicago
EYW
Key West
S$356 Return, found 2 days ago
S$356
Return
found 2 days ago
Select Delta flight, departing Wed, 21 May from Chicago to Key West, returning Wed, 28 May, priced at S$356 found 2 days ago
Delta
Wed, 21 May - Wed, 28 May
ORD
Chicago
EYW
Key West
S$382 Return, found 2 days ago
S$382
Return
found 2 days ago
Select Delta flight, departing Wed, 21 May from Chicago to Key West, returning Wed, 28 May, priced at S$382 found 2 days ago
Delta
Wed, 21 May - Wed, 28 May
ORD
Chicago
EYW
Key West
S$468 Return, found 2 days ago
S$468
Return
found 2 days ago
Select Delta flight, departing Wed, 21 May from Chicago to Key West, returning Wed, 28 May, priced at S$468 found 2 days ago
Delta
Wed, 21 May - Wed, 28 May
ORD
Chicago
EYW
Key West
S$495 Return, found 2 days ago
S$495
Return
found 2 days ago
Select Delta flight, departing Wed, 21 May from Chicago to Key West, returning Wed, 28 May, priced at S$495 found 2 days ago
American Airlines
Wed, 21 May - Wed, 28 May
ORD
Chicago
EYW
Key West
S$519 Return, found 2 days ago
S$519
Return
found 2 days ago
Select American Airlines flight, departing Wed, 21 May from Chicago to Key West, returning Wed, 28 May, priced at S$519 found 2 days ago
American Airlines
Wed, 21 May - Wed, 28 May
ORD
Chicago
EYW
Key West
S$532 Return, found 2 days ago
S$532
Return
found 2 days ago
Select American Airlines flight, departing Wed, 21 May from Chicago to Key West, returning Wed, 28 May, priced at S$532 found 2 days ago
United
Wed, 21 May - Wed, 28 May
ORD
Chicago
EYW
Key West
S$538 Return, found 2 days ago
S$538
Return
found 2 days ago
Select United flight, departing Wed, 21 May from Chicago to Key West, returning Wed, 28 May, priced at S$538 found 2 days ago
United
Wed, 21 May - Wed, 28 May
ORD
Chicago
EYW
Key West
S$550 Return, found 2 days ago
S$550
Return
found 2 days ago
Select United flight, departing Wed, 21 May from Chicago to Key West, returning Wed, 28 May, priced at S$550 found 2 days ago
American Airlines
Wed, 21 May - Wed, 28 May
ORD
Chicago
EYW
Key West
S$565 Return, found 2 days ago
S$565
Return
found 2 days ago
Select American Airlines flight, departing Wed, 21 May from Chicago to Key West, returning Wed, 28 May, priced at S$565 found 2 days ago
American Airlines
Wed, 21 May - Wed, 28 May
ORD
Chicago
EYW
Key West
S$578 Return, found 2 days ago
S$578
Return
found 2 days ago
Select American Airlines flight, departing Wed, 21 May from Chicago to Key West, returning Wed, 28 May, priced at S$578 found 2 days ago
Chicago to Key West route information
Origin airport
O'Hare Intl.
Destination airport
Key West Intl.
Return price
S$356
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 United, Delta, 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$274 and roundtrip prices from S$356*.
 

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$356. 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$355.60
*Available to Expedia members.