S$464 Cheap Flights from Chicago to Key West

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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$464 for one-way flights and S$1,200 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, 24 Mar - Mon, 31 Mar
MDW
Chicago
EYW
Key West
S$1,200 Return, found 1 day ago
S$1,200
Return
found 1 day ago
Select Delta flight, departing Mon, 24 Mar from Chicago to Key West, returning Mon, 31 Mar, priced at S$1,200 found 1 day ago
Delta
Mon, 24 Mar - Mon, 31 Mar
MDW
Chicago
EYW
Key West
S$1,363 Return, found 1 day ago
S$1,363
Return
found 1 day ago
Select Delta flight, departing Mon, 24 Mar from Chicago to Key West, returning Mon, 31 Mar, priced at S$1,363 found 1 day ago
Delta
Mon, 24 Mar - Mon, 31 Mar
MDW
Chicago
EYW
Key West
S$1,484 Return, found 1 day ago
S$1,484
Return
found 1 day ago
Select Delta flight, departing Mon, 24 Mar from Chicago to Key West, returning Mon, 31 Mar, priced at S$1,484 found 1 day ago
Delta
Mon, 24 Mar - Mon, 31 Mar
MDW
Chicago
EYW
Key West
S$1,647 Return, found 1 day ago
S$1,647
Return
found 1 day ago
Select Delta flight, departing Mon, 24 Mar from Chicago to Key West, returning Mon, 31 Mar, priced at S$1,647 found 1 day ago
Chicago to Key West route information
Origin airport
Midway Intl.
Destination airport
Key West Intl.
Airlines serving
Delta
Return price
S$1,200
Distance
1982 km

Flights from Chicago to Key West

When looking for plane tickets from Chicago to Key West, the ease and convenience of using Expedia simply can’t be beat. With tons of departure points and flights options from the top airline carriers, Expedia gives you the widest array of cheap flights to Key West. Look for MDW to EYW airfare with the assurance that you have the largest online travel agency working for you.

Expedia lets you search across the largest number of airlines and Key West flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Chicago Key West flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Chicago to Key West trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Key West flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from Chicago to Key West with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

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$1,200. 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.
Chicago Airports

Chicago

O'Hare Intl. to Key West
S$794.10
*Available to Expedia members.