MDW - EYW

$115 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 12/31. 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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Everything you should know

Cheapest round-trip
$287
Overall average: $306
Multiple Airlines
Thu 1/22Mon 1/26
MDW - EYW • 2 stops
Cheapest one-way
$115
Multiple Airlines
Wed 12/31
MDW - EYW • 2 stops
When to travel
January
Cheapest • 46% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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, Jan 22 - Mon, Jan 26
Multiple Airlines Logo
5:01 pm - 12:26 pm
MDW
-
EYW
18h 25m2 stops
Multiple Airlines Logo
1:06 pm - 7:58 pm
EYW
-
MDW
7h 52m1 stop
$287Multiple Airlines
Tue, Feb 24 - Thu, Mar 5
Delta Logo
6:00 am - 1:48 pm
MDW
-
EYW
6h 48m1 stop
Delta Logo
6:07 pm - 10:42 pm
EYW
-
MDW
5h 35m1 stop
$289Delta
Tue, Feb 10 - Thu, Feb 19
Delta Logo
12:48 pm - 7:40 pm
MDW
-
EYW
5h 52m1 stop
Delta Logo
6:07 pm - 6:37 pm
EYW
-
MDW
25h 30m2 stops
$292Delta
Wed, Mar 4 - Mon, Mar 9
Delta Logo
12:46 pm - 7:42 pm
MDW
-
EYW
5h 56m1 stop
Delta Logo
6:25 pm - 10:29 pm
EYW
-
MDW
5h 04m1 stop
$294Delta
Fri, Feb 6 - Mon, Feb 9
Multiple Airlines Logo
6:20 am - 10:09 am
MDW
-
EYW
26h 49m2 stops
Multiple Airlines Logo
1:06 pm - 7:58 pm
EYW
-
MDW
7h 52m1 stop
$300Multiple Airlines
Wed, Dec 24 - Mon, Dec 29
Multiple Airlines Logo
8:15 am - 11:20 am
MDW
-
EYW
26h 05m2 stops
Multiple Airlines Logo
1:10 pm - 9:58 pm
EYW
-
MDW
9h 48m1 stop
$301Multiple Airlines
Sun, Feb 15 - Fri, Feb 20
Multiple Airlines Logo
8:56 pm - 12:26 pm
MDW
-
EYW
14h 30m1 stop
Multiple Airlines Logo
1:06 pm - 7:50 pm
EYW
-
MDW
7h 44m1 stop
$302Multiple Airlines
Thu, Jan 22 - Mon, Jan 26
Multiple Airlines Logo
5:01 pm - 12:26 pm
MDW
-
EYW
18h 25m2 stops
Multiple Airlines Logo
1:06 pm - 7:58 pm
EYW
-
MDW
7h 52m1 stop
$304Multiple Airlines
Sat, Feb 21 - Wed, Feb 25
Delta Logo
11:01 am - 7:42 pm
MDW
-
EYW
7h 41m1 stop
Delta Logo
6:07 pm - 10:42 pm
EYW
-
MDW
5h 35m1 stop
$306Delta
Thu, Dec 18 - Mon, Dec 22
Multiple Airlines Logo
3:10 pm - 12:30 pm
MDW
-
EYW
20h 20m1 stop
Multiple Airlines Logo
1:10 pm - 9:58 pm
EYW
-
MDW
9h 48m1 stop
$311Multiple 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.

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 January, where tickets cost $306 (return) on average. On the other hand, the most expensive months are November and October, where the average cost of round-trip tickets is $1,356 and $998 respectively.

Find deals

Good to know

Low seasonAugust
Cheapest flight$115
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 24% 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 $122 for a one-way ticket and $294 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 8009 reviews
8.5Crew
7.3Food
7.9Comfort
7.9Entertainment
8.1Boarding
Airline reviews

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

2.0 MediocreAnonymous, Nov 2025
ATL - TPA
Read more Delta reviews

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

The flight was an hour and a half late departing which was inconvenient

The flight was great. The gate location was way to far away!!!

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.

Movie selection was meh. Food was great. Crew as always great. I paid for premium because that’s the only way not to feel like a sardine. That’s how economy should be imo. Sadly passengers have to pay an extra $1000 to get what they should at base price but that’s all airlines. The airline industry in general treats passengers as cargo.

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.

this crew didn't care much. bumping carts into seats more times than i care to remember

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)