EYW - MDW

$102 Find Cheap Flights from Key West to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Midway departing on 12/12. 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 Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Chicago, 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 Key West to Chicago, 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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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Key West to Midway (EYW-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to Midway 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 Key West to Midway

Mon, Nov 24 - Sat, Nov 29
Multiple Airlines Logo
8:55 am - 4:52 pmEYW-MDW
8h 57m1 stop
Multiple Airlines Logo
6:02 pm - 8:15 amMDW-EYW
13h 13m1 stop
$219Multiple Airlines
Find Deal
Thu, Nov 13 - Mon, Nov 17
Multiple Airlines Logo
8:55 am - 6:39 pmEYW-MDW
10h 44m2 stops
Multiple Airlines Logo
6:06 pm - 11:05 amMDW-EYW
15h 59m1 stop
$254Multiple Airlines
Find Deal
Mon, Nov 24 - Sat, Nov 29
Multiple Airlines Logo
8:55 am - 4:52 pmEYW-MDW
8h 57m1 stop
Multiple Airlines Logo
6:02 pm - 11:20 amMDW-EYW
16h 18m2 stops
$266Multiple Airlines
Find Deal
Tue, Feb 24 - Tue, Mar 10
Delta Logo
7:00 am - 12:01 pmEYW-MDW
6h 01m1 stop
Delta Logo
1:05 pm - 7:44 pmMDW-EYW
5h 39m1 stop
$269Delta
Find Deal
Thu, Feb 12 - Tue, Feb 17
Delta Logo
7:00 am - 12:01 pmEYW-MDW
6h 01m1 stop
Delta Logo
10:35 am - 5:13 pmMDW-EYW
5h 38m1 stop
$294Delta
Find Deal
Thu, Feb 12 - Tue, Feb 17
Delta Logo
7:00 am - 12:01 pmEYW-MDW
6h 01m1 stop
Delta Logo
10:35 am - 5:13 pmMDW-EYW
5h 38m1 stop
$299Delta
Find Deal
Fri, Dec 19 - Mon, Dec 22
Delta Logo
7:40 am - 11:55 amEYW-MDW
5h 15m1 stop
Delta Logo
12:45 pm - 9:34 pmMDW-EYW
7h 49m1 stop
$319Delta
Find Deal
Thu, Nov 13 - Mon, Nov 17
Delta Logo
12:26 pm - 4:38 pmEYW-MDW
5h 12m1 stop
Delta Logo
6:00 am - 11:31 amMDW-EYW
4h 31m1 stop
$329Delta
Find Deal
Fri, Feb 13 - Sun, Feb 15
Multiple Airlines Logo
1:06 pm - 7:50 pmEYW-MDW
7h 44m1 stop
Multiple Airlines Logo
8:56 pm - 12:26 pmMDW-EYW
14h 30m1 stop
$331Multiple Airlines
Find Deal
Fri, Feb 13 - Tue, Feb 17
Delta Logo
6:00 pm - 9:46 pmEYW-MDW
4h 46m1 stop
Delta Logo
1:05 pm - 7:44 pmMDW-EYW
5h 39m1 stop
$334Delta
Find Deal

Everything you should know

Cheapest round-trip
$219
Multiple Airlines
Mon 11/24Sat 11/29
EYW - MDW • 1 stop
Cheapest one-way
$102
Multiple Airlines
Fri 12/12
EYW - MDW • 1 stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Useful Info

Good to know

Cheapest flight$102
Flight from Key West to Chicago Midway Airport

When to book flights from Key West to Midway

Are your dates flexible? Find out the best times to travel from Key West to Midway 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 Key West to Chicago Midway Airport flights

  • What is the cheapest flight from Key West to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Key West to Chicago Midway Airport was $102 for a one-way ticket and $219 for a round-trip.

  • Do I need a passport to fly between Key West and Chicago Midway Airport?

    A passport is not required to fly from Key West to Chicago Midway Airport.

  • Which aircraft models fly most regularly from Key West to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from Key West to Chicago Midway Airport?

    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 Key West to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Key West to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Key West 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 Key West to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Key West with another airline. Booking your flights between Key West and MDW 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 Key West to Chicago Midway Airport?

    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 Chicago Midway Airport from Key West up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

Information on your arrival and departure airports

Key West (EYW)
Midway (MDW)

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