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$119+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$484
(Delta)

One-way from

$119
(Kiwi.com)

Popular in

March

Cheapest in

June

Average price

$453
From Key West to Chicago Midway
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One-way flight from Key West to Chicago Midway
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Highest demand for flights based on searches. 16% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/10. 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.
Fri 9/267:00 amEYW - MDW
1 stop5h 48mDelta
Tue 9/3012:43 pmMDW - EYW
1 stop6h 24mDelta
Deal found 9/10$484
This Delta deal was found by Cheapflights users on 9/11. 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 11/246:18 pmEYW - MDW
1 stop6h 14mDelta
Sat 11/2912:47 pmMDW - EYW
1 stop6h 06mDelta
Deal found 9/11$519

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 September 11, 2025.
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

Fri 9/26

7:00 am-11:48 am

1 stop5h 48m

Chicago Midway

Tue 9/30

12:43 pm-8:07 pm

1 stop6h 24m

$484

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 11/24

6:18 pm-11:32 pm

1 stop6h 14m

Chicago Midway

Sat 11/29

12:47 pm-7:53 pm

1 stop6h 06m

$519

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 3/10

6:00 pm-9:46 pm

1 stop4h 46m

Chicago Midway

Wed 3/11

10:35 am-5:12 pm

1 stop5h 37m

$527

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 11/14

9:01 am-2:37 pm

1 stop6h 36m

$119

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 11/13

8:55 am-5:15 pm

2 stops33h 20m

$134

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 11/14

2:25 pm-6:39 pm

2 stops29h 14m

$147

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 11/13

6:18 pm-11:32 pm

1 stop6h 14m

$264

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sun 10/19

6:17 pm-10:14 pm

1 stop4h 57m

$370

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sat 1/3

10:35 pm-12:33 pm

2 stops38h 58m

$477

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 1/1

2:25 pm-6:24 pm

2 stops28h 59m

$538

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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 48m. 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.

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

    Currently, April is the cheapest month in which you can book a flight from Key West to Chicago Midway Airport (average of $160). Flying from Key West to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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