MDW - EYW

$230 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 6/26. 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

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

 
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.

Recent round-trip flight deals from Midway to Key West

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to Key West.
Discover the best prices for you by selecting your travel dates on KAYAK.
Allegiant Air Logo
11:37 am - 4:36 pmMDW-EYW
27h 59m2 stops
Allegiant Air Logo
4:20 pm - 9:41 amEYW-MDW
18h 21m1 stop
$313Allegiant Air
Find Deal
Thu, Jul 31 - Sun, Aug 3
Delta Logo
12:44 pm - 7:39 pmMDW-EYW
5h 55m1 stop
Delta Logo
7:00 am - 11:53 amEYW-MDW
5h 53m1 stop
$323Delta
Find Deal
Sat, Jul 5 - Wed, Jul 9
Delta Logo
6:00 am - 1:09 pmMDW-EYW
6h 09m1 stop
Delta Logo
6:00 pm - 9:47 pmEYW-MDW
4h 47m1 stop
$326Delta
Find Deal
Fri, Aug 15 - Tue, Aug 19
Delta Logo
10:35 am - 5:15 pmMDW-EYW
5h 40m1 stop
Delta Logo
7:00 am - 11:55 amEYW-MDW
5h 55m1 stop
$329Delta
Find Deal
Fri, Aug 15 - Fri, Aug 22
Delta Logo
12:48 pm - 8:07 pmMDW-EYW
6h 19m1 stop
Delta Logo
7:30 am - 11:53 amEYW-MDW
5h 23m1 stop
$348Delta
Find Deal
Tue, May 20 - Sat, May 24
Delta Logo
12:48 pm - 8:07 pmMDW-EYW
6h 19m1 stop
Delta Logo
11:48 am - 3:20 pmEYW-MDW
4h 32m1 stop
$349Delta
Find Deal
Sat, May 17 - Tue, May 20
Delta Logo
12:44 pm - 7:39 pmMDW-EYW
5h 55m1 stop
Delta Logo
7:00 am - 11:53 amEYW-MDW
5h 53m1 stop
$351Delta
Find Deal
Sat, Jul 5 - Wed, Jul 9
Delta Logo
12:48 pm - 8:07 pmMDW-EYW
6h 19m1 stop
Delta Logo
7:00 am - 11:53 amEYW-MDW
5h 53m1 stop
$368Delta
Find Deal
Fri, May 30 - Wed, Jun 4
Allegiant Air Logo
11:37 am - 4:36 pmMDW-EYW
27h 59m2 stops
Allegiant Air Logo
8:54 am - 1:56 pmEYW-MDW
30h 02m2 stops
$381Allegiant Air
Find Deal
Thu, Jul 31 - Sun, Aug 3
Delta Logo
12:48 pm - 8:07 pmMDW-EYW
6h 19m1 stop
Delta Logo
7:00 am - 11:53 amEYW-MDW
5h 53m1 stop
$385Delta
Find Deal
Thu, May 29 - Tue, Jun 3
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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 September, where tickets cost $338 (return) on average. On the other hand, the most expensive months are April and February, where the average cost of round-trip tickets is $657 and $593 respectively.

Good to know

Low seasonDecember
High seasonSeptember
Cheapest flight$230
Best time to beat the crowds but there is an average 16% increase in price.
Most popular time to fly and prices are also 30% 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 $230 for a one-way ticket and $313 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.

Top airlines 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 7936 reviews
7.3Food
7.9Comfort
8.5Crew
7.9Entertainment
8.2Boarding
Airline reviews

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

8.0 ExcellentFredrick, Apr 2025GSO - DTW
Read more Delta reviews

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

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

Delta flight was on time, seats were comfortable, and crew was nice.

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 …

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

It was very cold because the air conditioner was on high power, and my son got sick.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

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

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