HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$128+ Cheap flights from Key West (EYW) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Key West to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Key West to Midway

Cheapest flights from Key West to Midway
Explore the most affordable flight options available from Key West to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/47:10 am
EYW
-
MDW
1 stop5h 49m
Delta
Sat 2/710:53 am
MDW
-
EYW
1 stop7h 47m
Delta
Deal found 1/25$410
This Kiwi.com deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/91:06 pm
EYW
-
MDW
1 stop7h 52m
Multiple Airlines
Fri 2/136:48 pm
MDW
-
EYW
2 stops38h 33m
Multiple Airlines
Deal found 1/25$446
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:30 am
EYW
-
MDW
1 stop5h 32m
Delta
Mon 4/136:00 am
MDW
-
EYW
1 stop6h 44m
Delta
Deal found 1/26$484
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/97:10 am
EYW
-
MDW
1 stop5h 49m
Delta
Fri 2/1312:45 pm
MDW
-
EYW
1 stop5h 57m
Delta
Deal found 1/25$859
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/86:06 pm
EYW
-
MDW
1 stop5h 16m
Delta
Fri 2/1312:45 pm
MDW
-
EYW
1 stop5h 57m
Delta
Deal found 1/26$956

Find flight deals from Key West to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$446
(Kiwi.com)

One-way from

$128
(Kiwi.com)
Provider with most accurate pricing for Key West-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Chicago Midway flights.
Search Deals
From Key West to Chicago Midway
Search Deals
One-way flight from Key West to Chicago Midway
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 26, 2026.
Use the filters below to find and compare flights from Key West to Chicago Midway Airport that are best for you.

Fly from

Key West

Fly to

Midway

Route

Depart

Return

Price

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 2/9

1:06 pm-7:58 pm

1 stop7h 52m

Chicago Midway

Fri 2/13

6:48 pm-10:21 am

2 stops38h 33m

$446

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 4/9

7:30 am-12:02 pm

1 stop5h 32m

Chicago Midway

Mon 4/13

6:00 am-1:44 pm

1 stop6h 44m

$484

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 2/9

7:10 am-11:59 am

1 stop5h 49m

Chicago Midway

Fri 2/13

12:45 pm-7:42 pm

1 stop5h 57m

$859

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sun 2/8

6:06 pm-10:22 pm

1 stop5h 16m

Chicago Midway

Fri 2/13

12:45 pm-7:42 pm

1 stop5h 57m

$956

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sun 3/8

9:46 am-1:08 pm

1 stop28h 22m

$128

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sun 2/8

10:27 pm-11:45 am

2 stops14h 18m

$148

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sun 4/5

9:46 am-10:19 pm

2 stops37h 33m

$165

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 3/13

1:06 pm-11:51 pm

1 stop11h 45m

$186

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sat 4/4

3:28 pm-10:21 pm

2 stops31h 53m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Compare providers for flights from Key West to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Key West to Midway in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Key West-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Key West-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Key West-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Key West to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Key West with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Key West to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Key West to Chicago Midway?

    If you book a flight to Chicago Midway from Key West, you will be flying from Key West, which is the city’s only airport. Key West (EYW) is located 2.6 mi from the center of Key West. There are 0 flights from Key West to Chicago Midway per day from 0 different airlines.

  • How long is the flight from Key West to Chicago Midway Airport?

    There are many flights that can get you from Key West to Chicago Midway Airport in 5h 32m. Fly via Delta to get the fastest option. There are 1238 mi between Key West and Chicago Midway Airport.

  • Can I find deals for flights from Key West to Midway that include hotel bookings?

    Yes. In addition to deals on Key West to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Key West to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Key West to Midway.

  • Can I find deals for business class flights from Key West to Midway?

    Yes. Cheapflights offers flight deals from Key West to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Key West to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Fort Lauderdale to O'Hare Intl flights
Miami to O'Hare Intl flights
Tampa to O'Hare Intl flights
Orlando to O'Hare Intl flights
Miami to Midway flights
Orlando to Midway flights
Fort Lauderdale to Midway flights
Jacksonville to O'Hare Intl flights
Tampa to Midway flights
West Palm Beach to O'Hare Intl flights
Fort Myers to O'Hare Intl flights
Jacksonville to Midway flights
Sarasota to O'Hare Intl flights
West Palm Beach to Midway flights
Fort Myers to Midway flights
Pensacola to O'Hare Intl flights
Panama City to O'Hare Intl flights
Fort Lauderdale to Rockford flights
Sarasota to Midway flights
Gainesville to O'Hare Intl flights
Panama City to Midway flights
Key West to O'Hare Intl flights
Pensacola to Midway flights
Valparaiso to O'Hare Intl flights
Tallahassee to O'Hare Intl flights
Gainesville to Midway flights
Orlando Sanford Intl to Rockford flights
Melbourne to O'Hare Intl flights
Tallahassee to Midway flights
Melbourne to Midway flights
St Petersburg to Rockford flights
Daytona Beach to Midway flights
Daytona Beach to O'Hare Intl flights
Valparaiso to Midway flights
Tampa to Rockford flights
Punta Gorda to Rockford flights
Orlando to Rockford flights
Pensacola to Rockford flights
Valdosta to O'Hare Intl flights
Fort Myers to Rockford flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.