$264 Cheap Flights from Chicago (MDW) to Key West (EYW)

View $264 flight on Tue, Nov 11, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $264 for one-way flights and $269 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Oct 14 - Tue, Oct 21
MDW
Chicago
EYW
Key West
$269 Roundtrip, found 22 hours ago
$269
Roundtrip
found 22 hours ago
Select Delta flight, departing Tue, Oct 14 from Chicago to Key West, returning Tue, Oct 21, priced at $269 found 22 hours ago
Delta
Sat, Aug 30 - Wed, Sep 3
MDW
Chicago
EYW
Key West
$279 Roundtrip, just found
$279
Roundtrip
just found
Select Delta flight, departing Sat, Aug 30 from Chicago to Key West, returning Wed, Sep 3, priced at $279 just found
Delta
Wed, Jul 30 - Tue, Aug 5
MDW
Chicago
EYW
Key West
$289 Roundtrip, found 21 hours ago
$289
Roundtrip
found 21 hours ago
Select Delta flight, departing Wed, Jul 30 from Chicago to Key West, returning Tue, Aug 5, priced at $289 found 21 hours ago
Delta
Fri, Nov 14 - Wed, Nov 19
MDW
Chicago
EYW
Key West
$299 Roundtrip, found 3 hours ago
$299
Roundtrip
found 3 hours ago
Select Delta flight, departing Fri, Nov 14 from Chicago to Key West, returning Wed, Nov 19, priced at $299 found 3 hours ago
Delta
Thu, Aug 14 - Thu, Aug 21
MDW
Chicago
EYW
Key West
$304 Roundtrip, found 3 days ago
$304
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Aug 14 from Chicago to Key West, returning Thu, Aug 21, priced at $304 found 3 days ago
Delta
Wed, Aug 20 - Sat, Aug 23
MDW
Chicago
EYW
Key West
$309 Roundtrip, found 1 day ago
$309
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Aug 20 from Chicago to Key West, returning Sat, Aug 23, priced at $309 found 1 day ago
Delta
Fri, Aug 15 - Tue, Aug 19
MDW
Chicago
EYW
Key West
$311 Roundtrip, found 5 days ago
$311
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Aug 15 from Chicago to Key West, returning Tue, Aug 19, priced at $311 found 5 days ago
Delta
Fri, Nov 14 - Sat, Nov 15
MDW
Chicago
EYW
Key West
$319 Roundtrip, found 3 hours ago
$319
Roundtrip
found 3 hours ago
Select Delta flight, departing Fri, Nov 14 from Chicago to Key West, returning Sat, Nov 15, priced at $319 found 3 hours ago
Delta
Tue, Jul 29 - Tue, Aug 5
MDW
Chicago
EYW
Key West
$320 Roundtrip, found 21 hours ago
$320
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Jul 29 from Chicago to Key West, returning Tue, Aug 5, priced at $320 found 21 hours ago
Delta
Sat, Aug 30 - Wed, Sep 3
MDW
Chicago
EYW
Key West
$330 Roundtrip, just found
$330
Roundtrip
just found
Select Delta flight, departing Sat, Aug 30 from Chicago to Key West, returning Wed, Sep 3, priced at $330 just found

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

January is typically the cheapest month to fly

From $242 - $806 per traveler.

Graph displaying average flight prices per month

Alternative airports near Key West

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Key West Intl. EYW. Cheapest and Closest option available. Average driving time to city center is 8 minutes. Flights from $384
EYW
Key West Intl.
CheapestClosest
Average driving time to city center8 min
Flights from $384
Flights from Chicago (MDW) to Key West (EYW)
Origin airport
Midway Intl.
Destination airport
Key West Intl.
Airlines serving
Delta
Roundtrip price
$268
Distance
1239 mi

Chicago to Key West Flights

The cheapest times to fly from Chicago to Key West

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Key West are during the month of October. You can find some of the cheapest flights from Chicago to Key West with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Key West

Sunday is one of the best days to book for cheap flights from Chicago to Key West: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Key West

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Key West in 2025. You can also book with separate airlines for your outbound and return journeys, from $264 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Key West flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Key West airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Key West Intl. Airport (EYW) cost?
Discover the latest flight deals from MDW to EYW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to EYW?
The cheapest flights from MDW to EYW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Key West Intl. Airport (EYW)?
You can't fly directly from Chicago, IL (MDW-Midway Intl.) to Key West Intl. Airport (EYW). However, you can find other airports with nonstop flights. Board your plane at O'Hare Intl. Airport (ORD) and head straight to Key West without layovers.
What is the cheapest airline that flies from MDW to EYW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to EYW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Key West Intl. Airport (EYW)?
You'll need to book a flight with a layover if you're traveling from Midway Intl. Airport (MDW) to Key West Intl. Airport (EYW). There are no daily direct flights on this route. However, just filter your search to include one or two stops to find an option that works for you.
What day of the week has the most flights from MDW to EYW?
Friday is generally the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can vary depending on various factors, such as the season and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Key West Intl. Airport (EYW)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Key West Intl. Airport (EYW) route, fly before 3 PM. Departures after this hour have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Key West Intl. Airport (EYW) last-minute?
Waiting until just before your trip to book a flight from MDW to EYW generally means paying more. While it's possible to find some last-minute deals, they're not always guaranteed. Keep your travel plans flexible to maximize your chances of landing a bargain.
Is it cheaper to book a MDW to EYW flight and hotel package?
You'll generally save money by securing a MDW to EYW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one convenient place. Once you've chosen your ideal accommodations and flights, consider adding extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Key West Intl. Airport (EYW)?
Usually, it's possible to cancel or reschedule your MDW to EYW flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more information on our Customer Service portal.

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*Available to One Key members.