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Key West

$160+ Cheap flights from Midway (MDW) to Key West (EYW)

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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Midway to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Key West (EYW). 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 17, 2025.

Round-trip from

$241
(Kiwi.com)

One-way from

$160
(Kiwi.com)

Popular in

November

Cheapest in

July

Average price

$434
From Chicago Midway to Key West
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One-way flight from Chicago Midway to Key West
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Highest demand for flights based on searches. 21% potential increase in price ($132 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 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 Midway to Key West

Cheapest flights from Midway to Key West
Explore the most affordable flight options available from Midway to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Thu 10/1611:49 amMDW - EYW
1 stop19h 26mMultiple Airlines
Thu 10/233:30 pmEYW - MDW
1 stop25h 50mMultiple Airlines
Deal found 9/16$241
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/2511:31 amMDW - EYW
1 stop19h 44mMultiple Airlines
Tue 10/2811:45 amEYW - MDW
2 stops25h 56mMultiple Airlines
Deal found 9/15$250
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Sat 10/411:21 amMDW - EYW
1 stop19h 54mMultiple Airlines
Tue 10/711:45 amEYW - MDW
2 stops26h 53mMultiple Airlines
Deal found 9/16$263
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Thu 10/1611:49 amMDW - EYW
1 stop19h 26mMultiple Airlines
Mon 10/209:57 amEYW - MDW
1 stop7h 12mMultiple Airlines
Deal found 9/16$267
This Delta deal was found by Cheapflights users on 9/16. 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.
Sun 12/146:00 amMDW - EYW
1 stop7h 06mDelta
Sat 12/206:20 pmEYW - MDW
1 stop4h 56mDelta
Deal found 9/16$269
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 9/2710:51 amMDW - EYW
1 stop20h 24mMultiple Airlines
Sat 10/49:52 amEYW - MDW
1 stop27h 52mMultiple Airlines
Deal found 9/15$274
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/236:24 pmMDW - EYW
2 stops13h 53mMultiple Airlines
Mon 10/272:57 pmEYW - MDW
1 stop5h 37mMultiple Airlines
Deal found 9/15$277
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/77:50 amMDW - EYW
1 stop25h 17mMultiple Airlines
Tue 11/1111:45 amEYW - MDW
2 stops25h 56mMultiple Airlines
Deal found 9/16$284
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/139:00 amMDW - EYW
1 stop25h 05mMultiple Airlines
Mon 10/209:57 amEYW - MDW
1 stop7h 12mMultiple Airlines
Deal found 9/15$288
This Delta deal was found by Cheapflights users on 9/15. 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 10/1512:48 pmMDW - EYW
1 stop6h 18mDelta
Wed 10/2212:22 pmEYW - MDW
1 stop4h 47mDelta
Deal found 9/15$289

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Key West 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 17, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Key West that are best for you.

Fly from

Midway

Fly to

Key West

Route

Depart

Return

Price

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 12/15

12:50 pm-8:03 pm

1 stop6h 13m

Key West

Sat 12/20

6:20 pm-10:16 pm

1 stop4h 56m

$269

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 10/13

9:00 am-11:05 am

1 stop25h 05m

Key West

Mon 10/20

9:57 am-9:00 pm

2 stops12h 03m

$295

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 10/16

11:49 am-8:15 am

1 stop19h 26m

Key West

Sun 10/19

8:55 am-8:31 am

2 stops24h 36m

$301

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 11/8

11:36 am-8:15 am

1 stop19h 39m

Key West

Tue 11/11

11:45 am-12:41 pm

2 stops25h 56m

$314

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 12/14

6:00 am-2:06 pm

1 stop7h 06m

Key West

Mon 12/22

6:20 pm-5:19 pm

2 stops23h 59m

$317

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 9/23

2:32 pm-9:07 am

2 stops17h 35m

Key West

Thu 9/25

8:55 am-8:53 am

1 stop24h 58m

$339

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 11/3

6:00 am-1:02 pm

1 stop6h 02m

Key West

Thu 11/27

12:26 pm-4:39 pm

1 stop5h 13m

$384

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 12/11

10:49 am-5:10 pm

1 stop5h 21m

Key West

Tue 12/16

6:05 pm-11:32 pm

1 stop6h 27m

$384

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 12/13

7:02 pm-2:06 pm

2 stops18h 04m

Key West

Fri 12/19

6:05 pm-11:32 pm

1 stop6h 27m

$435

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 11/16

6:00 am-2:03 pm

1 stop7h 03m

Key West

Sun 11/23

6:18 pm-11:32 pm

1 stop6h 14m

$439

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 13 results
1
2

Best time to book a flight from Midway to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Midway 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Key West

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

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Key West (average of $328). Flying from Chicago Midway Airport to Key West in March is currently the most expensive (average of $491). 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.

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Key West. Reviews last updated September 17, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Key West, such as Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from Midway to Key West. 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 into for flights to Key West from Chicago Midway?

    Key West (EYW), located 2.6 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Key West. 1 airline have flights to Key West from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Key West should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

  • How long is the flight from Chicago Midway Airport to Key West?

    Departing from Chicago Midway Airport to Key West will take you 6h 13m. Chicago Midway Airport and Key West are separated by a distance of 1238 mi.

  • What is the cheapest airline to fly from Chicago Midway Airport to Key West round-trip?

    Flying on Delta is currently your cheapest option to Key West, with prices starting at $248. Users have found that Delta is 48% cheaper than the other options available to this destination.

  • Can I find deals for flights from Midway to Key West that include hotel bookings?

    Yes. In addition to deals on Midway to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Key West.

  • Can I find deals for business class flights from Midway to Key West?

    Yes. Cheapflights offers flight deals from Midway to Key West 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 Chicago Midway Airport to Key West?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Key West (average of $328). Flying from Chicago Midway Airport to Key West in March is currently the most expensive (average of $491). 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

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Top airline flying from Midway to Key West

Discover the top airline that operate flights from Midway to Key West. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$538FlexibilityNo cancel feeOn-timeN/A

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