MDW to EYW (Chicago to Key West) Flights

Last Minute Flights from MDW to EYW

Best airfare and ticket deals for MDW to EYW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
MDWKey WestApril 27 to April 28$738
*Prices include taxes and fees

Cheapest MDW to EYW Flights

Best airfare and ticket deals for MDW to EYW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
MDWKey WestJuly 9 to July 23$208
MDWKey WestMay 31 to June 4$222
MDWKey WestJune 18 to July 9$228
MDWKey WestMay 31 to June 6$242
*Prices include taxes and fees
MDW to EYW Flight Details
Origin airport
Midway Intl.
Origin airport IATA code
MDW
Destination airport
Key West Intl.
Destination airport IATA code
EYW
Distance
1239 mi

Frequently asked questions

Which airlines with flights from MDW to Key West, FL Airport (EYW-Key West Intl.) allow free cancellation due to COVID-19?
We make it easy to find fares with cancellation flexibility due to COVID-19. After entering your travel dates, simply click on “No change fee.” It’s directly underneath the “Flexible change policies” heading to the left. Like always, remember to read through the airline’s terms and conditions thoroughly before you book your Chicago, IL Airport (MDW-Midway Intl.) to Key West, FL Airport (EYW-Key West Intl.) flights.
What airlines fly direct from Chicago, IL Airport (MDW-Midway Intl.) to Key West, FL Airport (EYW-Key West Intl.)?
Unfortunately, there aren’t any airlines that fly straight from Chicago, IL Airport (MDW-Midway Intl.) to EYW. You’ll need to book a trip with at least one stop.
How many flights are there from MDW to EYW?
About 4 flights are scheduled every day between Chicago, IL Airport (MDW-Midway Intl.) and Key West, FL Airport (EYW-Key West Intl.). Buckle up because your plane to Key West is ready to take to the skies.
How long does it take to fly from Chicago, IL Airport (MDW-Midway Intl.) to Key West, FL Airport (EYW-Key West Intl.)?
On average, 3 hours and 33 minutes. Booked on a daytime flight? Secure a seat by a window and enjoy the views. Or, if you’re departing from Chicago, IL Airport (MDW-Midway Intl.) to Key West, FL Airport (EYW-Key West Intl.) in the evening, have a nap and land in Key West feeling well rested.
What is the flight distance from Chicago, IL Airport (MDW-Midway Intl.) to Key West, FL Airport (EYW-Key West Intl.)?
At 1250 miles (2000 km), this medium-haul flight is no never-ending marathon, but it’s no joyride either. Get to Key West feeling well rested by catching some z’s en route.
How many morning flights are there from MDW to EYW?
Buckle up and journey from MDW to EYW on one of the 14 morning flights each week. Delta (DL) operates 14 of these services that take off before noon. 6:01AM is the earliest departure time you can book with DL.
How many afternoon flights are there from MDW to EYW?
With 16 weekly afternoon and evening flights from MDW to EYW, forget about that hotel wake-up call. Look up the offers from Delta (DL) and select from 16 flights each week scheduled after midday. The first leaves the runway at 12:40PM.
What is the earliest departure time out of Chicago to Key West?
6:01AM is the earliest scheduled flight you can get out of MDW, arriving at EYW at 6:38PM. Save valuable time in the morning by having your suitcase zipped up and ready to go.
What is the latest departure time out of Chicago to Key West?
The latest flight is scheduled to depart MDW at 6:35PM and comes in at 6:38PM at EYW. You’ll have plenty of time to get ready for this flight.
What is the average price from Chicago to Key West?
Flights from MDW to EYW are available for around $208. Act fast, because deals this good tend to go quick! This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Chicago to Key West Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from Chicago to Key West to attend your cousin’s wedding, to pitch a business idea to your boss, or perhaps simply to treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find the cheapest flights from MDW to EYW, we’ve got you covered here at Flights.com.

We present you with some of the hottest deals on airfare so stop that Google flights search. We want you to spend less on your flight from Chicago to Key West, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.