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$161+ 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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
May 28 — Jun 41
Thu 5/28
Thu 6/4
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 April 28, 2026.

This Delta deal was found by Cheapflights users on 4/25. 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 5/207:30 am
EYW
-
MDW
1 stop5h 26m
Delta
Wed 5/2710:59 am
MDW
-
EYW
1 stop5h 24m
Delta
Deal found 4/25$329
This Delta deal was found by Cheapflights users on 4/23. 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.
Fri 10/26:00 pm
EYW
-
MDW
1 stop4h 46m
Delta
Sun 10/41:05 pm
MDW
-
EYW
1 stop5h 40m
Delta
Deal found 4/23$379
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:11 pm
EYW
-
MDW
2 stops9h 51m
Multiple Airlines
Sun 5/312:47 pm
MDW
-
EYW
1 stop17h 54m
Multiple Airlines
Deal found 4/23$397
This Delta deal was found by Cheapflights users on 4/23. 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.
Fri 5/87:30 am
EYW
-
MDW
1 stop5h 26m
Delta
Tue 5/1210:59 am
MDW
-
EYW
1 stop5h 24m
Delta
Deal found 4/23$424
This Delta deal was found by Cheapflights users on 4/25. 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 9/256:00 pm
EYW
-
MDW
1 stop4h 46m
Delta
Sat 9/2610:35 am
MDW
-
EYW
1 stop5h 39m
Delta
Deal found 4/25$474
This Delta deal was found by Cheapflights users on 4/26. 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.
Fri 5/297:30 am
EYW
-
MDW
1 stop5h 26m
Delta
Sun 5/3110:59 am
MDW
-
EYW
1 stop7h 50m
Delta
Deal found 4/26$559
This Delta deal was found by Cheapflights users on 4/26. 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.
Mon 5/117:30 am
EYW
-
MDW
1 stop5h 26m
Delta
Fri 5/1512:53 pm
MDW
-
EYW
1 stop5h 56m
Delta
Deal found 4/26$757

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 April 28, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$329
(Delta)

One-way from

$161
(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.
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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 April 28, 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
Quickest round-trip

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 5/20

7:30 am-11:56 am

1 stop5h 26m

Chicago Midway

Wed 5/27

10:59 am-5:23 pm

1 stop5h 24m

$329

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sat 5/9

3:30 pm-9:09 pm

1 stop6h 39m

Chicago Midway

Wed 5/13

6:23 am-12:27 pm

1 stop5h 04m

$424

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 5/8

7:30 am-11:56 am

1 stop5h 26m

Chicago Midway

Tue 5/12

10:59 am-5:23 pm

1 stop5h 24m

$424

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 5/29

7:30 am-11:56 am

1 stop5h 26m

Chicago Midway

Sun 5/31

10:59 am-7:49 pm

1 stop7h 50m

$559

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 5/11

7:30 am-11:56 am

1 stop5h 26m

Chicago Midway

Fri 5/15

12:53 pm-7:49 pm

1 stop5h 56m

$757

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 9/25

6:00 pm-9:46 pm

1 stop4h 46m

Chicago Midway

Sat 9/26

9:30 am-7:45 pm

2 stops9h 15m

$957

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 10/2

11:45 am-6:31 pm

2 stops7h 46m

Chicago Midway

Sun 10/4

1:05 pm-7:45 pm

1 stop5h 40m

$982
Cheapest one-way

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 8/11

1:14 pm-2:27 pm

2 stops50h 13m

$227
Quickest one-way

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sat 7/18

11:45 am-3:37 pm

1 stop4h 52m

$294

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 6/17

6:24 pm-10:17 pm

1 stop4h 53m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/26

Showing 1-10 of 11 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 26m. 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
Hammond
Porter

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