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$132+ 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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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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 July 27, 2026.

This Delta deal was found by Cheapflights users on 7/26. 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.
Sat 9/54:00 pm
EYW
-
MDW
1 stop7h 36m
Delta
Sun 9/66:05 am
MDW
-
EYW
1 stop5h 21m
Delta
Deal found 7/26$332
This Delta deal was found by Cheapflights users on 7/25. 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.
Sat 10/106:11 pm
EYW
-
MDW
1 stop5h 22m
Delta
Sun 10/1110:59 am
MDW
-
EYW
1 stop5h 16m
Delta
Deal found 7/25$339
This Delta deal was found by Cheapflights users on 7/25. 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.
Thu 10/17:40 am
EYW
-
MDW
1 stop5h 14m
Delta
Sat 10/311:35 am
MDW
-
EYW
1 stop7h 25m
Delta
Deal found 7/25$367
This Delta deal was found by Cheapflights users on 7/23. 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 9/37:40 am
EYW
-
MDW
1 stop5h 11m
Delta
Sun 9/66:05 am
MDW
-
EYW
1 stop5h 21m
Delta
Deal found 7/23$399
This Delta deal was found by Cheapflights users on 7/24. 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 9/46:15 pm
EYW
-
MDW
1 stop5h 21m
Delta
Sun 9/66:05 am
MDW
-
EYW
1 stop5h 21m
Delta
Deal found 7/24$409
This Delta deal was found by Cheapflights users on 7/22. 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 8/67:40 am
EYW
-
MDW
1 stop5h 11m
Delta
Mon 8/1010:54 am
MDW
-
EYW
1 stop5h 26m
Delta
Deal found 7/22$434
This Delta deal was found by Cheapflights users on 7/25. 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.
Fri 10/96:10 pm
EYW
-
MDW
2 stops16h 07m
Delta
Sun 10/1110:59 am
MDW
-
EYW
1 stop5h 16m
Delta
Deal found 7/25$468
This Delta deal was found by Cheapflights users on 7/24. 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 9/311:48 am
EYW
-
MDW
1 stop5h 27m
Delta
Mon 9/76:05 am
MDW
-
EYW
1 stop5h 55m
Delta
Deal found 7/24$529
This Delta deal was found by Cheapflights users on 7/25. 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 11/26:11 pm
EYW
-
MDW
1 stop5h 22m
Delta
Tue 11/36:04 am
MDW
-
EYW
1 stop7h 16m
Delta
Deal found 7/25$597
This Delta deal was found by Cheapflights users on 7/25. 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 10/77:40 am
EYW
-
MDW
1 stop5h 10m
Delta
Fri 10/912:45 pm
MDW
-
EYW
1 stop6h 16m
Delta
Deal found 7/25$628

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 July 27, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$332
(Delta)

One-way from

$132
(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
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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 July 27, 2026.
Use the filters below to find and compare flights from Key West to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 10/1

11:42 am-4:15 pm

1 stop5h 33m

Chicago Midway

Sat 10/3

11:35 am-8:00 pm

1 stop7h 25m

$332
Quickest round-trip

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 9/3

7:40 am-11:51 am

1 stop5h 11m

Chicago Midway

Sun 9/6

6:05 am-12:26 pm

1 stop5h 21m

$399

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 10/1

11:42 am-4:15 pm

1 stop5h 33m

Chicago Midway

Sun 10/4

6:05 am-12:53 pm

1 stop5h 48m

$399

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 10/16

6:10 pm-10:33 pm

1 stop5h 23m

Chicago Midway

Sun 10/18

12:45 pm-8:01 pm

1 stop6h 16m

$399

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 9/4

6:15 pm-10:36 pm

1 stop5h 21m

Chicago Midway

Sun 9/6

6:05 am-12:26 pm

1 stop5h 21m

$409

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 8/6

7:40 am-11:51 am

1 stop5h 11m

Chicago Midway

Mon 8/10

10:54 am-5:20 pm

1 stop5h 26m

$434

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 10/9

6:10 pm-9:17 am

2 stops16h 07m

Chicago Midway

Sun 10/11

10:59 am-5:15 pm

1 stop5h 16m

$468

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 11/4

4:00 pm-10:33 pm

1 stop7h 33m

Chicago Midway

Thu 11/5

11:39 am-8:01 pm

1 stop7h 22m

$597

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 11/2

6:11 pm-10:33 pm

1 stop5h 22m

Chicago Midway

Tue 11/3

6:04 am-2:20 pm

1 stop7h 16m

$597
Cheapest one-way

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 8/21

1:11 pm-10:47 pm

2 stops34h 36m

$150

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 15 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on Key West-Chicago Midway Airport flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Key West-Chicago Midway Airport flight deals on Cheapflights vs. Expedia <90% 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 Expedia the most. Expedia 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 33m. 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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