MDW - EYW

$149 Find Cheap Flights from Chicago Midway Airport to Key West - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Key West departing on 9/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$285
Allegiant Air
Thu 8/13Thu 8/20
MDW - EYW • 1 stop
Cheapest one-way
$149
Multiple Airlines
Sat 9/26
MDW - EYW • 2 stops
Top airlines
Cheapest • from $329 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Midway and Key West. You'll need at least 1 connection.
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Flight Deals
Useful Info
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Key West that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Key West

Thu, Aug 13 - Thu, Aug 20
Multiple Airlines Logo
2:49 pm - 9:41 am
MDW
-
EYW
17h 52m
1 stop
Multiple Airlines Logo
11:04 am - 10:47 pm
EYW
-
MDW
12h 43m
2 stops
$285Multiple Airlines
Sun, Aug 16 - Sun, Aug 23
Multiple Airlines Logo
2:49 pm - 9:41 am
MDW
-
EYW
17h 52m
1 stop
Multiple Airlines Logo
12:05 pm - 10:47 pm
EYW
-
MDW
11h 42m
2 stops
$306Multiple Airlines
Sun, Aug 16 - Sun, Aug 23
Multiple Airlines Logo
2:49 pm - 9:41 am
MDW
-
EYW
17h 52m
1 stop
Multiple Airlines Logo
12:05 pm - 10:47 pm
EYW
-
MDW
11h 42m
2 stops
$307Multiple Airlines
Sun, Aug 16 - Sun, Aug 23
Multiple Airlines Logo
2:49 pm - 9:41 am
MDW
-
EYW
17h 52m
1 stop
Multiple Airlines Logo
12:05 pm - 10:47 pm
EYW
-
MDW
11h 42m
2 stops
$308Multiple Airlines
Thu, Jul 23 - Mon, Jul 27
Multiple Airlines Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
Multiple Airlines Logo
1:11 pm - 11:07 am
EYW
-
MDW
22h 56m
2 stops
$323Multiple Airlines
Thu, Jul 30 - Thu, Aug 6
Multiple Airlines Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
Multiple Airlines Logo
11:04 am - 10:03 pm
EYW
-
MDW
11h 59m
2 stops
$324Multiple Airlines
Fri, Aug 14 - Tue, Aug 18
Delta Logo
10:54 am - 5:20 pm
MDW
-
EYW
5h 26m
1 stop
Delta Logo
11:48 am - 4:15 pm
EYW
-
MDW
5h 27m
1 stop
$329Delta
Thu, Jul 16 - Sun, Jul 19
Allegiant Air Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
Allegiant Air Logo
10:55 am - 2:38 pm
EYW
-
MDW
28h 43m
1 stop
$347Allegiant Air
Sat, Sep 12 - Tue, Sep 15
Delta Logo
11:35 am - 8:01 pm
MDW
-
EYW
7h 26m
1 stop
Delta Logo
7:40 am - 11:55 am
EYW
-
MDW
5h 15m
1 stop
$354Delta
Thu, Jul 30 - Mon, Aug 3
Multiple Airlines Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
Multiple Airlines Logo
4:41 pm - 11:07 am
EYW
-
MDW
19h 26m
2 stops
$356Multiple Airlines
Useful Info

KAYAK's insights & trends for Midway to Key West flights

Get data-powered insights and trends into flights from Midway to Key West to help you find the cheapest flights, the best time to fly and much more.

How long does a flight from Chicago Midway Airport to Key West take?

There are no direct flights for this route. The shortest travel duration to get to Key West from Chicago Midway Airport is 3h 39m.

Good to know

Cheapest flight$149
Flight from Chicago Midway Airport to Key West

When to book flights from Midway to Key West

Are your dates flexible? Find out the best times to travel from Midway to Key West based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Key West flights

  • What is the cheapest flight from Chicago Midway Airport to Key West?

    In the last 5 days, the lowest price for a flight from Chicago Midway Airport to Key West was $149 for a one-way ticket and $285 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Key West?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Key West?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Key West?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Key West.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Key West?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Key West.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Key West?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Key West from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Key West?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Key West with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and EYW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Key West?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Key West from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago Midway Airport to Key West?

    In the past 5 days, the cheapest round-trip tickets from Chicago Midway Airport to Key West were found on Delta ($329) and Allegiant Air ($347).

Reviews of the top airline flying from Midway to Key West

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Key West. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Key West? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
DeltaOverall score based on 8453 reviews
7.8Entertainment
7.8Comfort
7.2Food
8.5Crew
8.1Boarding
Airline reviews

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

2.0 MediocreJean, Jun 2026
MDW - ATL
Read more Delta reviews

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Everything you need to know for your flight from Midway to Key West

Information on your arrival and departure airports