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

View $264 flight on Wed, Feb 18, 2026Opens in a new window

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

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

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
Fri, Oct 31 - Mon, Nov 3
EYW
Key West
MDW
Chicago
$269 Roundtrip, found 7 hours ago
$269
Roundtrip
found 7 hours ago
Select Delta flight, departing Fri, Oct 31 from Key West to Chicago, returning Mon, Nov 3, priced at $269 found 7 hours ago
Delta
Wed, Oct 15 - Tue, Oct 21
EYW
Key West
MDW
Chicago
$289 Roundtrip, found 10 hours ago
$289
Roundtrip
found 10 hours ago
Select Delta flight, departing Wed, Oct 15 from Key West to Chicago, returning Tue, Oct 21, priced at $289 found 10 hours ago
Delta
Thu, Nov 13 - Wed, Dec 3
EYW
Key West
MDW
Chicago
$309 Roundtrip, found 4 days ago
$309
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Nov 13 from Key West to Chicago, returning Wed, Dec 3, priced at $309 found 4 days ago
Delta
Wed, Oct 29 - Wed, Nov 5
EYW
Key West
MDW
Chicago
$320 Roundtrip, found 9 hours ago
$320
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Oct 29 from Key West to Chicago, returning Wed, Nov 5, priced at $320 found 9 hours ago
Delta
Fri, Jan 30 - Mon, Feb 2
EYW
Key West
MDW
Chicago
$324 Roundtrip, found 5 days ago
$324
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Jan 30 from Key West to Chicago, returning Mon, Feb 2, priced at $324 found 5 days ago
Delta
Sat, Nov 15 - Tue, Nov 25
EYW
Key West
MDW
Chicago
$337 Roundtrip, found 4 days ago
$337
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Nov 15 from Key West to Chicago, returning Tue, Nov 25, priced at $337 found 4 days ago
Delta
Thu, Oct 2 - Tue, Oct 21
EYW
Key West
MDW
Chicago
$339 Roundtrip, found 5 days ago
$339
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Oct 2 from Key West to Chicago, returning Tue, Oct 21, priced at $339 found 5 days ago
Delta
Thu, Nov 13 - Sat, Nov 29
EYW
Key West
MDW
Chicago
$340 Roundtrip, found 3 days ago
$340
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Nov 13 from Key West to Chicago, returning Sat, Nov 29, priced at $340 found 3 days ago
Delta
Thu, Jan 29 - Sun, Feb 1
EYW
Key West
MDW
Chicago
$344 Roundtrip, found 1 day ago
$344
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jan 29 from Key West to Chicago, returning Sun, Feb 1, priced at $344 found 1 day ago
Delta
Wed, Nov 19 - Sat, Dec 6
EYW
Key West
MDW
Chicago
$344 Roundtrip, found 5 days ago
$344
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Nov 19 from Key West to Chicago, returning Sat, Dec 6, priced at $344 found 5 days ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $451
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $451

Frequently asked questions

How much does a flight from Key West Intl. Airport (EYW) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $264 or cheap return flight from $269 from Key West Intl. Airport (EYW) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Key West Intl. Airport (EYW) to Midway Intl. Airport (MDW)?
Flying in October is a great way to save, as it's the cheapest month for flights between EYW and MDW. You'll often find the lowest prices during off-peak months.
What is the cheapest airline that flies from Key West Intl. Airport (EYW) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll fly you from EYW to MDW. Then, sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Key West Intl. Airport (EYW) to Midway Intl. Airport (MDW)?
There are no daily nonstop flights available from Key West Intl. Airport (EYW) to Midway Intl. Airport (MDW). But you can opt for flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from EYW to MDW?
Usually you'll find the largest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can vary depending on the time of year, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Key West Intl. Airport (EYW) to Midway Intl. Airport (MDW)?
To reach Midway Intl. Airport (MDW) on schedule, opt for a flight that takes off from Key West Intl. Airport (EYW) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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.
What airports do you fly into for Chicago from Key West Intl. Airport (EYW)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Key West Intl. Airport (EYW). Consider your options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Key West Intl. Airport (EYW) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from EYW to MDW right before your getaway is typically more expensive. But if there's some wiggle room with your schedule, you could bag a cheap last-minute fare.
Is it cheaper to book an EYW to MDW flight and hotel package?
Booking an EYW to MDW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our wide range of hotels and then add car rentals, activities and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Key West Intl. Airport (EYW) to Midway Intl. Airport (MDW)?
Typically, it's possible to cancel or reschedule your EYW to MDW flight. However, for bookings made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Travel information

Origin airport
Key West Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$268
Distance
1239 mi

Book with confidence

Book with confidence

Key West to Chicago Flights

The cheapest times to fly from Key West to Chicago

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 Key West to Chicago are during the month of October. You can find some of the cheapest flights from Key West to Chicago with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from Key West to Chicago: 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 Key West to Chicago

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 Key West to Chicago 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 Key West to Chicago 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 Key West to Chicago 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.

 

Key West to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.