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$116+ 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 12/22. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 December 12, 2025.

This Delta deal was found by Cheapflights users on 12/10. 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.
Mon 12/297:25 amEYW - MDW
1 stop5h 33mDelta
Mon 1/126:45 amMDW - EYW
1 stop6h 03mDelta
Deal found 12/10$299
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 12/221:10 pmEYW - MDW
1 stop9h 48mMultiple Airlines
Tue 12/232:01 pmMDW - EYW
2 stops19h 38mMultiple Airlines
Deal found 12/9$586
This Delta deal was found by Cheapflights users on 12/11. 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.
Fri 12/2611:47 amEYW - MDW
1 stop5h 33mDelta
Tue 12/3012:45 pmMDW - EYW
1 stop7h 13mDelta
Deal found 12/11$619
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/261:10 pmEYW - MDW
1 stop9h 48mMultiple Airlines
Tue 12/302:01 pmMDW - EYW
2 stops18h 38mMultiple Airlines
Deal found 12/11$665
This Delta deal was found by Cheapflights users on 12/9. 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 12/227:25 amEYW - MDW
1 stop5h 33mDelta
Tue 12/239:50 amMDW - EYW
1 stop6h 32mDelta
Deal found 12/9$908
This Delta deal was found by Cheapflights users on 12/10. 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.
Thu 12/254:25 pmEYW - MDW
1 stop6h 57mDelta
Mon 12/299:50 amMDW - EYW
1 stop6h 32mDelta
Deal found 12/10$991
This Delta deal was found by Cheapflights users on 12/11. 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.
Wed 12/244:25 pmEYW - MDW
1 stop6h 57mDelta
Sun 12/2812:45 pmMDW - EYW
1 stop7h 13mDelta
Deal found 12/11$1,040
This Delta deal was found by Cheapflights users on 12/10. 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.
Sat 12/204:47 pmEYW - MDW
1 stop6h 35mDelta
Sat 12/276:00 amMDW - EYW
1 stop5h 07mDelta
Deal found 12/10$1,521

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 December 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$299
(Delta)

One-way from

$116
(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 December 12, 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

Mon 12/29

7:25 am-11:58 am

1 stop5h 33m

Chicago Midway

Mon 1/12

6:45 am-1:48 pm

1 stop6h 03m

$299

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 1/21

6:06 pm-10:22 pm

1 stop5h 16m

Chicago Midway

Thu 1/29

10:48 am-5:11 pm

1 stop5h 23m

$334

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 12/22

1:10 pm-9:58 pm

1 stop9h 48m

Chicago Midway

Tue 12/23

2:01 pm-10:39 am

2 stops19h 38m

$586

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 12/26

11:47 am-4:20 pm

1 stop5h 33m

Chicago Midway

Tue 12/30

12:45 pm-8:58 pm

1 stop7h 13m

$619

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 12/26

1:10 pm-9:58 pm

1 stop9h 48m

Chicago Midway

Tue 12/30

2:01 pm-9:39 am

2 stops18h 38m

$665

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 12/22

7:25 am-11:58 am

1 stop5h 33m

Chicago Midway

Tue 12/23

9:50 am-5:22 pm

1 stop6h 32m

$908

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 4/9

6:25 pm-10:29 pm

1 stop5h 04m

Chicago Midway

Mon 4/13

9:30 am-7:44 pm

2 stops9h 14m

$917

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 12/22

1:10 pm-9:58 pm

1 stop9h 48m

$116

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 12/25

8:55 am-9:58 pm

1 stop14h 03m

$155

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 12/29

1:10 pm-10:12 pm

2 stops10h 02m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

Showing 1-10 of 14 results
1
2

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 December.
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 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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