MDW - EYW

$101 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 11/27. 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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Everything you should know

Cheapest round-trip
$291
Typical prices: $433-$1,492
Multiple Airlines
Fri 11/14Thu 11/20
MDW - EYW • 1 stop
Cheapest one-way
$101
Multiple Airlines
Thu 11/27
MDW - EYW • 1 stop
Top airlines
Delta
Cheapest • from $294 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
July
Cheapest • 35% 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

Fri, Nov 14 - Thu, Nov 20
Multiple Airlines Logo
5:57 pm - 10:07 amMDW-EYW
15h 10m1 stop
Multiple Airlines Logo
8:55 am - 4:30 pmEYW-MDW
8h 35m1 stop
$291Multiple Airlines
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Thu, Nov 20 - Mon, Nov 24
Multiple Airlines Logo
8:41 pm - 10:07 amMDW-EYW
36h 26m2 stops
Multiple Airlines Logo
8:55 am - 4:52 pmEYW-MDW
8h 57m1 stop
$292Multiple Airlines
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Tue, Dec 2 - Tue, Dec 9
Delta Logo
10:49 am - 5:15 pmMDW-EYW
5h 26m1 stop
Delta Logo
6:10 pm - 11:47 pmEYW-MDW
6h 37m1 stop
$294Delta
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Fri, Nov 14 - Mon, Nov 17
Multiple Airlines Logo
5:35 pm - 9:01 amMDW-EYW
14h 26m2 stops
Multiple Airlines Logo
9:57 am - 12:30 amEYW-MDW
15h 33m1 stop
$295Multiple Airlines
Find Deal
Fri, Nov 14 - Fri, Nov 21
Multiple Airlines Logo
5:35 pm - 9:01 amMDW-EYW
14h 26m2 stops
Multiple Airlines Logo
8:55 am - 11:29 pmEYW-MDW
15h 34m1 stop
$298Multiple Airlines
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Sat, Nov 22 - Thu, Nov 27
Multiple Airlines Logo
6:02 pm - 8:15 amMDW-EYW
13h 13m1 stop
Multiple Airlines Logo
12:15 pm - 10:43 pmEYW-MDW
11h 28m2 stops
$305Multiple Airlines
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Fri, Nov 14 - Mon, Nov 17
Allegiant Air Logo
5:35 pm - 9:01 amMDW-EYW
14h 26m2 stops
Allegiant Air Logo
10:41 am - 3:22 pmEYW-MDW
5h 41m1 stop
$311Allegiant Air
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Sat, Jan 31 - Sat, Feb 7
Delta Logo
10:46 am - 5:13 pmMDW-EYW
5h 27m1 stop
Delta Logo
6:08 pm - 10:26 pmEYW-MDW
5h 18m1 stop
$324Delta
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Thu, Nov 20 - Mon, Nov 24
Delta Logo
6:00 am - 2:03 pmMDW-EYW
7h 03m1 stop
Delta Logo
12:26 pm - 4:39 pmEYW-MDW
5h 13m1 stop
$326Delta
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Fri, Nov 28 - Thu, Dec 4
Delta Logo
6:00 am - 2:03 pmMDW-EYW
7h 03m1 stop
Delta Logo
6:10 pm - 11:47 pmEYW-MDW
6h 37m1 stop
$334Delta
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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 November.

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 July, where tickets cost $343 (return) on average. On the other hand, the most expensive months are October and November, where the average cost of round-trip tickets is $1,043 and $677 respectively.

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Good to know

Low seasonAugust
Cheapest flight$101
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 18% 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 $101 for a one-way ticket and $291 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 8001 reviews
7.9Comfort
8.5Crew
8.2Boarding
7.3Food
7.9Entertainment
Airline reviews

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

10.0 ExcellentMAYRA, Nov 2025JFK - MIA
Read more Delta reviews

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 was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

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)