S$337 Cheap Flights from Chicago to Key West

View S$337 flight on Tue, 19 Aug, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Key West Intl. Airport (EYW)

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

Prices were available within the past 7 days and start at S$337 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
Fri, 8 Aug - Wed, 13 Aug
MDW
Chicago
EYW
Key West
S$343 Return, found 4 days ago
S$343
Return
found 4 days ago
Select Delta flight, departing Fri, 8 Aug from Chicago to Key West, returning Wed, 13 Aug, priced at S$343 found 4 days ago
Delta
Tue, 19 Aug - Tue, 26 Aug
MDW
Chicago
EYW
Key West
S$369 Return, found 1 hour ago
S$369
Return
found 1 hour ago
Select Delta flight, departing Tue, 19 Aug from Chicago to Key West, returning Tue, 26 Aug, priced at S$369 found 1 hour ago
Delta
Fri, 8 Aug - Wed, 13 Aug
MDW
Chicago
EYW
Key West
S$397 Return, found 4 days ago
S$397
Return
found 4 days ago
Select Delta flight, departing Fri, 8 Aug from Chicago to Key West, returning Wed, 13 Aug, priced at S$397 found 4 days ago
Delta
Fri, 8 Aug - Wed, 13 Aug
MDW
Chicago
EYW
Key West
S$409 Return, found 4 days ago
S$409
Return
found 4 days ago
Select Delta flight, departing Fri, 8 Aug from Chicago to Key West, returning Wed, 13 Aug, priced at S$409 found 4 days ago
Delta
Tue, 19 Aug - Tue, 26 Aug
MDW
Chicago
EYW
Key West
S$430 Return, found 1 hour ago
S$430
Return
found 1 hour ago
Select Delta flight, departing Tue, 19 Aug from Chicago to Key West, returning Tue, 26 Aug, priced at S$430 found 1 hour ago
Delta
Wed, 20 Aug - Wed, 27 Aug
MDW
Chicago
EYW
Key West
S$478 Return, found 1 day ago
S$478
Return
found 1 day ago
Select Delta flight, departing Wed, 20 Aug from Chicago to Key West, returning Wed, 27 Aug, priced at S$478 found 1 day ago
Delta
Fri, 8 Aug - Wed, 13 Aug
MDW
Chicago
EYW
Key West
S$484 Return, found 4 days ago
S$484
Return
found 4 days ago
Select Delta flight, departing Fri, 8 Aug from Chicago to Key West, returning Wed, 13 Aug, priced at S$484 found 4 days ago
Delta
Wed, 20 Aug - Wed, 27 Aug
MDW
Chicago
EYW
Key West
S$490 Return, found 1 day ago
S$490
Return
found 1 day ago
Select Delta flight, departing Wed, 20 Aug from Chicago to Key West, returning Wed, 27 Aug, priced at S$490 found 1 day ago
Delta
Fri, 8 Aug - Wed, 13 Aug
MDW
Chicago
EYW
Key West
S$495 Return, found 4 days ago
S$495
Return
found 4 days ago
Select Delta flight, departing Fri, 8 Aug from Chicago to Key West, returning Wed, 13 Aug, priced at S$495 found 4 days ago
Delta
Fri, 8 Aug - Wed, 13 Aug
MDW
Chicago
EYW
Key West
S$516 Return, found 4 days ago
S$516
Return
found 4 days ago
Select Delta flight, departing Fri, 8 Aug from Chicago to Key West, returning Wed, 13 Aug, priced at S$516 found 4 days ago
Delta
Fri, 8 Aug - Wed, 13 Aug
MDW
Chicago
EYW
Key West
S$592 Return, found 4 days ago
S$592
Return
found 4 days ago
Select Delta flight, departing Fri, 8 Aug from Chicago to Key West, returning Wed, 13 Aug, priced at S$592 found 4 days ago
Delta
Fri, 8 Aug - Wed, 13 Aug
MDW
Chicago
EYW
Key West
S$657 Return, found 4 days ago
S$657
Return
found 4 days ago
Select Delta flight, departing Fri, 8 Aug from Chicago to Key West, returning Wed, 13 Aug, priced at S$657 found 4 days ago
Delta
Fri, 8 Aug - Wed, 13 Aug
MDW
Chicago
EYW
Key West
S$679 Return, found 4 days ago
S$679
Return
found 4 days ago
Select Delta flight, departing Fri, 8 Aug from Chicago to Key West, returning Wed, 13 Aug, priced at S$679 found 4 days ago
Delta
Fri, 8 Aug - Wed, 13 Aug
MDW
Chicago
EYW
Key West
S$684 Return, found 4 days ago
S$684
Return
found 4 days ago
Select Delta flight, departing Fri, 8 Aug from Chicago to Key West, returning Wed, 13 Aug, priced at S$684 found 4 days ago
Delta
Mon, 18 Aug - Mon, 25 Aug
MDW
Chicago
EYW
Key West
S$694 Return, found 2 days ago
S$694
Return
found 2 days ago
Select Delta flight, departing Mon, 18 Aug from Chicago to Key West, returning Mon, 25 Aug, priced at S$694 found 2 days ago
Delta
Mon, 18 Aug - Mon, 25 Aug
MDW
Chicago
EYW
Key West
S$764 Return, found 2 days ago
S$764
Return
found 2 days ago
Select Delta flight, departing Mon, 18 Aug from Chicago to Key West, returning Mon, 25 Aug, priced at S$764 found 2 days ago
Delta
Mon, 18 Aug - Mon, 25 Aug
MDW
Chicago
EYW
Key West
S$840 Return, found 2 days ago
S$840
Return
found 2 days ago
Select Delta flight, departing Mon, 18 Aug from Chicago to Key West, returning Mon, 25 Aug, priced at S$840 found 2 days ago

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

January is typically the cheapest month to fly

From S$308 - S$1,026 per traveller.

Graph displaying average flight prices per month

Chicago to Key West route information
Origin airport
Midway Intl.
Destination airport
Key West Intl.
Airlines serving
Delta
Return price
S$343
Distance
1982 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. Our selection of flights from Midway 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 Midway 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$337 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 Midway Intl. Airport (MDW) to EYW?
The lowest price advertised for a round-trip flight from Midway Airport to Key West Intl. Airport (EYW) is S$343. But you better move fast. This figure is based on fares available within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Chicago Airport to Key West Intl. Airport (EYW)?
Every air carrier has its own set of terms and conditions. If you do decide to cancel, follow the instructions on our Customer Service Portal.
How do I find cheap flights from Chicago Airport to Key West Intl. Airport 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 MDW to Key West Intl. Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from MDW to Key West Intl. Airport (EYW)?
The flying distance between Midway Airport and Key West Intl. Airport (EYW) is 2,000 kilometres. Work your way through your travel song playlist or make a start on the latest bestseller and the journey will whiz by.
Which airlines fly direct from Midway Intl. Airport (MDW) to EYW?
Right now, no airlines offer flights directly from Midway Intl. Airport (MDW) to Key West Intl. Airport (EYW). You'll need to book a flight with at least one stop. To get the best connections and price, lock in your fare ahead of time.
Are Midway Airport to Key West Intl. Airport (EYW) flight tickets cheaper when they're purchased at the last minute?
It is possible to get amazing last-minute deals from MDW to Key West Intl. Airport, but it's also possible to miss out entirely! As many airlines release seats up to a year in advance, it's worthwhile keeping an eye on fares early and being ready to book when you spot a bargain. Expedia compares air carrier prices and updates flight deals all the time, so you can rest easy knowing you're always getting the latest offers.

Explore a world of travel with Expedia

Chicago Airports

Chicago

O'Hare Intl. to Key West
S$342.90
*Available to Expedia members.