MDW - EYW

$264 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 7/29. 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

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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Flights 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

Wed, Aug 13 - Wed, Aug 20
Delta Logo
10:31 am - 5:27 pmMDW-EYW
5h 56m1 stop
Delta Logo
2:00 pm - 5:47 pmEYW-MDW
4h 47m1 stop
$269Delta
Find Deal
Wed, Sep 3 - Sat, Sep 6
Delta Logo
10:31 am - 5:25 pmMDW-EYW
5h 54m1 stop
Delta Logo
11:52 am - 3:28 pmEYW-MDW
4h 36m1 stop
$289Delta
Find Deal
Sat, Aug 16 - Sat, Aug 23
Delta Logo
6:04 am - 1:05 pmMDW-EYW
6h 01m1 stop
Delta Logo
11:52 am - 3:28 pmEYW-MDW
4h 36m1 stop
$320Delta
Find Deal
Sat, Aug 2 - Thu, Aug 7
Delta Logo
12:43 pm - 7:49 pmMDW-EYW
6h 06m1 stop
Delta Logo
7:00 am - 11:48 amEYW-MDW
5h 48m1 stop
$334Delta
Find Deal
Fri, Oct 24 - Tue, Oct 28
Delta Logo
1:05 pm - 7:44 pmMDW-EYW
5h 39m1 stop
Delta Logo
6:00 pm - 9:44 pmEYW-MDW
4h 44m1 stop
$354Delta
Find Deal
Thu, Oct 30 - Sun, Nov 2
Allegiant Air Logo
6:40 pm - 8:55 pmMDW-EYW
25h 15m2 stops
Allegiant Air Logo
8:33 pm - 4:37 pmEYW-MDW
21h 04m2 stops
$377Allegiant Air
Find Deal
Wed, Oct 8 - Sun, Oct 12
Delta Logo
1:05 pm - 7:44 pmMDW-EYW
5h 39m1 stop
Delta Logo
6:00 pm - 9:44 pmEYW-MDW
4h 44m1 stop
$384Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27
Allegiant Air Logo
11:07 am - 9:16 amMDW-EYW
21h 09m2 stops
Allegiant Air Logo
2:57 pm - 7:34 pmEYW-MDW
5h 37m1 stop
$389Allegiant Air
Find Deal
Tue, Jul 15 - Tue, Jul 22
Delta Logo
6:00 am - 1:08 pmMDW-EYW
6h 08m1 stop
Delta Logo
6:00 pm - 9:42 pmEYW-MDW
4h 42m1 stop
$404Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27
 Logo
11:07 am - 9:16 amMDW-EYW
21h 09m2 stops
 Logo
8:47 am - 7:34 pmEYW-MDW
11h 47m2 stops
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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.

What is the cheapest month to fly from Chicago Midway Airport to Key West?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Key West, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Key West is October, where tickets cost $225 (return) on average. On the other hand, the most expensive months are February and November, where the average cost of round-trip tickets is $593 and $572 respectively.

Good to know

Low seasonMay
High seasonSeptember
Cheapest flight$264
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 20% 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 $264 for a one-way ticket and $269 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.
8.0
DeltaOverall score based on 7975 reviews
7.3Food
8.2Boarding
8.5Crew
7.9Comfort
7.9Entertainment
Airline reviews

After all the weather issues at least they got me to my destination the next day

4.0 OkayAnonymous, Jul 2025HSV - ATL
Read more Delta reviews

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Crew was friendly Love the entertainment in the seat head rest.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

This was a code share Latam Airlines flight - everything very good except there was no seatback entertainment

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

Loyal Delta traveler, but last nights flight was a train wreck. Seated in 1B after multiple delays. Then we couldn’t takeoff because of an issue with the passenger that was ‘not in compliance’ and had to deplane along with the threat if they did not deplane, all the passengers would be required to do so. Finally they were escorted off, but the experience threw off the crew. Disruptive for everyone. Service was a mess, televisions didn’t work, bathroom door kept swinging open during the entire flight whenever empty …

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

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