MDW - EYW

$121 Find Cheap Flights from Chicago Midway Airport to Key West

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 5/27. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Key West

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Key West, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Key West, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$315
Typical prices: $480-$441
Allegiant Air
Thu 7/30Wed 8/5
MDW - EYW • 1 stop
Cheapest one-way
$121
Multiple Airlines
Wed 5/27
MDW - EYW • 2 stops
Top airlines
Delta
Cheapest • from $329 (round-trip)
Delta
Best reviews • 7.9 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.
Insights
Insights
Insights
Insights
Top layover airports
Miami (MIA)
Cheapest • Avg $313 (round-trip)
Miami (MIA)
Shortest trip • 4h 57m (one-way)
Insights
Insights
Insights
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Key West!
Flight Deals
Booking Insights
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, Jul 30 - Wed, Aug 5
Multiple Airlines Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
Multiple Airlines Logo
11:46 am - 10:11 pm
EYW
-
MDW
11h 25m
2 stops
$315Multiple 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
12:05 pm - 10:11 pm
EYW
-
MDW
11h 06m
2 stops
$316Multiple Airlines
Sun, Jun 14 - Wed, Jun 17
Multiple Airlines Logo
2:46 pm - 9:41 am
MDW
-
EYW
17h 55m
1 stop
Multiple Airlines Logo
11:46 am - 10:11 pm
EYW
-
MDW
11h 25m
2 stops
$326Multiple Airlines
Sun, Jun 14 - Thu, Jun 25
Multiple Airlines Logo
2:46 pm - 9:41 am
MDW
-
EYW
17h 55m
1 stop
Multiple Airlines Logo
12:05 pm - 10:11 pm
EYW
-
MDW
11h 06m
2 stops
$328Multiple Airlines
Mon, Jul 27 - Thu, Aug 6
Delta Logo
11:05 am - 7:51 pm
MDW
-
EYW
7h 46m
1 stop
Delta Logo
6:18 pm - 10:15 pm
EYW
-
MDW
4h 57m
1 stop
$329Delta
Thu, Jul 30 - Mon, Aug 3
Multiple Airlines Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
Multiple Airlines Logo
12:07 pm - 10:11 pm
EYW
-
MDW
11h 04m
2 stops
$332Multiple Airlines
Thu, Jul 23 - Thu, Jul 30
Multiple Airlines Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
Multiple Airlines Logo
12:05 pm - 10:11 pm
EYW
-
MDW
11h 06m
2 stops
$333Multiple Airlines
Thu, Jun 25 - Sun, Jun 28
Multiple Airlines Logo
2:46 pm - 9:41 am
MDW
-
EYW
17h 55m
1 stop
Multiple Airlines Logo
9:16 pm - 2:07 pm
EYW
-
MDW
17h 51m
2 stops
$334Multiple Airlines
Thu, Jul 30 - Fri, Aug 7
Multiple Airlines Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
Multiple Airlines Logo
1:11 pm - 10:11 pm
EYW
-
MDW
10h 00m
2 stops
$335Multiple Airlines
Sun, Jul 26 - Thu, Jul 30
Multiple Airlines Logo
2:48 pm - 9:41 am
MDW
-
EYW
17h 53m
1 stop
Multiple Airlines Logo
12:05 pm - 10:11 pm
EYW
-
MDW
11h 06m
2 stops
$339Multiple Airlines
Booking Insights

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 much is a round-trip flight from Chicago Midway Airport to Key West?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Key West departing in July.
Find deals

Good to know

Low seasonMay
Cheapest flight$121
Best time to beat the crowds with an average 40% drop in price.
Most popular time to fly and prices are also 17% lower on average.
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 3 days, the lowest price for a flight from Chicago Midway Airport to Key West was $121 for a one-way ticket and $315 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.

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.
7.9
DeltaOverall score based on 8392 reviews
8.5Crew
7.9Comfort
7.2Food
8.1Boarding
7.8Entertainment
Airline reviews

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

8.0 ExcellentPaul A, Apr 2026
ORD - ATL
Read more Delta reviews

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

N Everything was perfect from boarding to assistance to baggage in Tampa

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.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

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

The whole experience was excellent. As it most often is with Delta

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Key West (EYW)