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$102+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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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 October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/149:01 amEYW - MDW
1 stop6h 36mMultiple Airlines
Sun 11/166:06 pmMDW - EYW
1 stop14h 11mMultiple Airlines
Deal found 10/26$193
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/79:01 amEYW - MDW
1 stop6h 06mMultiple Airlines
Sat 11/151:37 pmMDW - EYW
2 stops19h 42mMultiple Airlines
Deal found 10/28$236
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/79:57 amEYW - MDW
1 stop5h 25mMultiple Airlines
Mon 11/106:06 pmMDW - EYW
1 stop15h 59mMultiple Airlines
Deal found 10/28$257
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Tue 11/1111:45 amEYW - MDW
2 stops25h 56mMultiple Airlines
Sat 11/1511:36 amMDW - EYW
1 stop19h 39mMultiple Airlines
Deal found 10/27$320
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Tue 10/2811:45 amEYW - MDW
2 stops25h 56mMultiple Airlines
Sun 11/910:12 amMDW - EYW
1 stop9h 34mMultiple Airlines
Deal found 10/27$363
This Delta deal was found by Cheapflights users on 10/27. 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.
Tue 10/286:17 pmEYW - MDW
1 stop4h 57mDelta
Sun 11/910:47 amMDW - EYW
1 stop5h 36mDelta
Deal found 10/27$400
This Delta deal was found by Cheapflights users on 10/26. 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 11/246:18 pmEYW - MDW
1 stop6h 22mDelta
Sat 11/2910:47 amMDW - EYW
1 stop5h 36mDelta
Deal found 10/26$559

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 October 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$193
(Kiwi.com)

One-way from

$102
(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
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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 October 28, 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 11/14

9:01 am-2:37 pm

1 stop6h 36m

Chicago Midway

Sun 11/16

6:06 pm-9:17 am

1 stop14h 11m

$193

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 11/7

9:01 am-2:07 pm

1 stop6h 06m

Chicago Midway

Sat 11/15

1:37 pm-10:19 am

2 stops19h 42m

$236

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 11/7

9:57 am-2:22 pm

1 stop5h 25m

Chicago Midway

Mon 11/10

6:06 pm-11:05 am

1 stop15h 59m

$257

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 2/12

7:00 am-12:01 pm

1 stop6h 01m

Chicago Midway

Tue 2/17

10:35 am-5:13 pm

1 stop5h 38m

$299

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 2/12

7:00 am-12:01 pm

1 stop6h 01m

Chicago Midway

Mon 2/16

1:05 pm-7:44 pm

1 stop5h 39m

$299

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 11/11

11:45 am-12:41 pm

2 stops25h 56m

Chicago Midway

Sat 11/15

11:36 am-8:15 am

1 stop19h 39m

$320

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 2/13

6:00 pm-9:46 pm

1 stop4h 46m

Chicago Midway

Mon 2/16

1:05 pm-7:44 pm

1 stop5h 39m

$334

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 2/13

6:00 pm-9:46 pm

1 stop4h 46m

Chicago Midway

Tue 2/17

1:05 pm-7:44 pm

1 stop5h 39m

$334

Key WestChicago

EYW - MDW

EYWMDW

Key West

Sat 2/14

2:25 pm-11:25 pm

2 stops10h 00m

Chicago Midway

Sun 2/15

8:56 pm-12:26 pm

1 stop14h 30m

$358

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 2/13

1:06 pm-7:50 pm

1 stop7h 44m

Chicago Midway

Sun 2/15

6:00 am-9:09 am

2 stops26h 09m

$405

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 19 results
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 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 6h 01m. 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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