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Key West

$140+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Aug 21 — Aug 281
Thu 8/21
Thu 8/28
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 August 16, 2025.

Round-trip from

$269
(Delta)

One-way from

$140
(Kiwi.com)

Popular in

February

Cheapest in

October

Average price

$438
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. 1% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 16, 2025.

This Delta deal was found by Cheapflights users on 8/13. 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 9/56:00 amMDW - EYW
1 stop6h 05mDelta
Thu 9/116:00 pmEYW - MDW
1 stop4h 36mDelta
Deal found 8/13$269
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/162:32 pmMDW - EYW
2 stops17h 40mMultiple Airlines
Thu 9/254:50 pmEYW - MDW
1 stop20h 54mMultiple Airlines
Deal found 8/13$286
This Delta deal was found by Cheapflights users on 8/13. 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 10/256:00 amMDW - EYW
1 stop6h 02mDelta
Fri 10/314:00 pmEYW - MDW
1 stop7h 14mDelta
Deal found 8/13$289
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 11/32:45 pmMDW - EYW
1 stop4h 36mAllegiant Air
Mon 11/1010:41 amEYW - MDW
1 stop5h 41mAllegiant Air
Deal found 8/14$304
This Delta deal was found by Cheapflights users on 8/13. 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 11/111:05 pmMDW - EYW
1 stop5h 39mDelta
Tue 11/187:00 amEYW - MDW
1 stop5h 55mDelta
Deal found 8/13$337
This Delta deal was found by Cheapflights users on 8/14. 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 11/191:05 pmMDW - EYW
1 stop5h 39mDelta
Sat 11/226:00 pmEYW - MDW
1 stop4h 44mDelta
Deal found 8/14$371
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 9/256:20 amMDW - EYW
2 stops27h 59mMultiple Airlines
Sun 9/2812:29 pmEYW - MDW
1 stop24h 31mMultiple Airlines
Deal found 8/15$377
This Delta deal was found by Cheapflights users on 8/15. 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.
Thu 12/111:05 pmMDW - EYW
1 stop5h 39mDelta
Tue 12/166:00 pmEYW - MDW
1 stop4h 44mDelta
Deal found 8/15$384
This Delta deal was found by Cheapflights users on 8/13. 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 8/226:04 amMDW - EYW
1 stop6h 01mDelta
Tue 8/267:00 amEYW - MDW
1 stop7h 36mDelta
Deal found 8/13$385
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 11/32:45 pmMDW - EYW
1 stop4h 36mMultiple Airlines
Mon 11/109:40 amEYW - MDW
2 stops15h 50mMultiple Airlines
Deal found 8/14$395
This Delta deal was found by Cheapflights users on 8/14. 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 10/226:00 amMDW - EYW
1 stop6h 02mDelta
Sat 10/256:17 pmEYW - MDW
1 stop4h 57mDelta
Deal found 8/14$404

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 August 16, 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

Wed 9/24

12:43 pm-8:07 pm

1 stop6h 24m

Key West

Tue 9/30

6:00 pm-9:36 pm

1 stop4h 36m

$269

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 10/25

6:00 am-1:02 pm

1 stop6h 02m

Key West

Wed 10/29

6:17 pm-10:14 pm

1 stop4h 57m

$269

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 9/23

10:35 am-5:15 pm

1 stop5h 40m

Key West

Wed 10/1

6:00 pm-9:36 pm

1 stop4h 36m

$269

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 10/21

12:48 pm-8:06 pm

1 stop6h 18m

Key West

Wed 10/29

6:17 pm-10:14 pm

1 stop4h 57m

$269

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 9/30

6:00 am-1:02 pm

1 stop6h 02m

Key West

Tue 10/7

6:17 pm-10:14 pm

1 stop4h 57m

$269

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 9/24

12:43 pm-8:07 pm

1 stop6h 24m

Key West

Wed 10/1

6:00 pm-9:36 pm

1 stop4h 36m

$269

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 9/23

12:43 pm-8:07 pm

1 stop6h 24m

Key West

Tue 9/30

7:00 am-11:48 am

1 stop5h 48m

$269

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 10/25

6:00 am-1:02 pm

1 stop6h 02m

Key West

Thu 10/30

6:17 pm-10:14 pm

1 stop4h 57m

$289

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 10/21

12:48 pm-8:06 pm

1 stop6h 18m

Key West

Sat 10/25

6:17 pm-10:14 pm

1 stop4h 57m

$289

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 10/21

12:48 pm-8:06 pm

1 stop6h 18m

Key West

Thu 10/30

6:17 pm-10:14 pm

1 stop4h 57m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Showing 1-10 of 22 results
1
2
3

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 $492). 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 August 16, 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
7,985 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

Overall

8.0

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
7,985 reviews
Delta
8.0
Very good
7,985 reviews

Boarding

8.2

Comfort

7.9

Food

7.3

Entertainment

7.9

Crew

8.5

Overall

8.0

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.

  • 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 $225. 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 $492). 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 August 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$225Average$526FlexibilityNo cancel feeOn-timeN/A

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