MDW to EYW (Chicago to Key West) Flights

Last Minute Flights from MDW to EYW

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
MDWKey WestMarch 20 to March 24$690
*Prices include taxes and fees

Cheapest MDW to EYW Flights

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
MDWKey WestAugust 22 to August 26$247
MDWKey WestOctober 26 to October 30$267
MDWKey WestAugust 22 to August 26$268
MDWKey WestApril 28 to May 1$287
*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

What airlines fly direct from Midway Intl. Airport (MDW) to EYW?
Unfortunately, there aren't any airlines flying straight from Midway Airport to Key West Intl. Airport (EYW). You'll need to book a flight with one or more stops.
How many flights are there from MDW to EYW?
Approximately 4 flights operate every day from Chicago, IL (MDW-Midway Intl.) to Key West, FL (EYW-Key West Intl.). Buckle up because your plane to Key West is ready to leave.
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Key West, FL (EYW-Key West Intl.)?
While you won't be cooped up in your seat for hours and hours from Chicago, IL (MDW-Midway Intl.) to Key West, FL (EYW-Key West Intl.), 3 hours and 49 minutes is no quick trip either. Think about upgrading your airfare if you'd prefer extra legroom.
What is the flight distance from Chicago, IL (MDW-Midway Intl.) to Key West, FL (EYW-Key West Intl.)?
At 1,250 miles (2,000 1), this medium-haul flight is no lengthy marathon, but it's no quick hop either. Arrive in Key West feeling rested by having a snooze en route.
How many morning flights are there from MDW to EYW?
Fasten your seat belt and get from MDW to EYW on one of the 14 morning flights each week. Delta Air Lines (DL) lists 14 weekly flights that leave before midday. 6:00AM is the earliest departure time available with this airline.
How many afternoon flights are there from MDW to EYW?
Say no to the crazy early check in and select one of the 16 weekly afternoon and evening flights from MDW to EYW. Afternoon and evening services advertised by Delta Air Lines (DL) leave from 12:42PM. In total, this carrier offers 16 weekly flights departing after midday.
What is the earliest departure time out of Chicago to Key West?
Leave MDW at 6:00AM and hit the tarmac at EYW at 7:40PM. This flight is the earliest you can get on this route.
What is the latest departure time out of Chicago to Key West?
From MDW, the latest flight you can get sets out at 6:50PM and arrives at EYW at 7:40PM. If you're not a big fan of early starts, this flight has your name on it.
What is the average price from Chicago to Key West?
Round-trip journeys from MDW to EYW start from $247. Book soon and score a bargain. 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 simply treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find our cheapest flights from MDW to EYW, we’ve got you covered here at Flights.com.

We present you with some of the most affordable 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.

Plan Your Trip