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$125+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Feb 3 — Feb 101
Tue 2/3
Tue 2/10
1 adult, Economy
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Cheap 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 January 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/2. 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 1/305:01 pmMDW - EYW
2 stops16h 08mMultiple Airlines
Fri 2/61:06 pmEYW - MDW
1 stop7h 46mMultiple Airlines
Deal found 1/2$285
This Kiwi.com deal was found by Cheapflights users on 1/2. 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 3/1711:19 amMDW - EYW
1 stop22h 52mMultiple Airlines
Mon 3/239:49 amEYW - MDW
2 stops37h 30mMultiple Airlines
Deal found 1/2$287
This Kiwi.com deal was found by Cheapflights users on 1/4. 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 1/305:01 pmMDW - EYW
2 stops16h 08mMultiple Airlines
Mon 2/21:06 pmEYW - MDW
1 stop7h 52mMultiple Airlines
Deal found 1/4$291
This Delta deal was found by Cheapflights users on 1/4. 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 2/2111:06 amMDW - EYW
1 stop7h 36mDelta
Wed 2/255:56 pmEYW - MDW
1 stop5h 35mDelta
Deal found 1/4$294
This Delta deal was found by Cheapflights users on 1/2. 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 1/1912:48 pmMDW - EYW
1 stop5h 52mDelta
Wed 1/286:06 pmEYW - MDW
1 stop5h 16mDelta
Deal found 1/2$299
This Kiwi.com deal was found by Cheapflights users on 1/1. 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 3/244:33 pmMDW - EYW
1 stop17h 38mMultiple Airlines
Tue 3/3112:25 pmEYW - MDW
2 stops10h 54mMultiple Airlines
Deal found 1/1$317
This Kiwi.com deal was found by Cheapflights users on 1/4. 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.
Sun 2/81:00 pmMDW - EYW
1 stop22h 26mMultiple Airlines
Sun 2/152:25 pmEYW - MDW
2 stops23h 43mMultiple Airlines
Deal found 1/4$322
This Delta deal was found by Cheapflights users on 1/2. 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 4/1110:45 amMDW - EYW
1 stop5h 45mDelta
Thu 4/166:25 pmEYW - MDW
1 stop5h 04mDelta
Deal found 1/2$324
This Kiwi.com deal was found by Cheapflights users on 1/2. 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 2/265:16 pmMDW - EYW
2 stops19h 14mMultiple Airlines
Mon 3/21:06 pmEYW - MDW
1 stop8h 21mMultiple Airlines
Deal found 1/2$328
This Kiwi.com deal was found by Cheapflights users on 1/3. 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 1/235:01 pmMDW - EYW
2 stops16h 08mMultiple Airlines
Mon 1/261:06 pmEYW - MDW
1 stop7h 52mMultiple Airlines
Deal found 1/3$331
This Delta deal was found by Cheapflights users on 1/2. 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 1/1711:21 amMDW - EYW
1 stop4h 58mDelta
Tue 1/276:06 pmEYW - MDW
1 stop5h 16mDelta
Deal found 1/2$334
This Delta deal was found by Cheapflights users on 1/2. 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 1/1311:21 amMDW - EYW
1 stop4h 50mDelta
Tue 1/276:06 pmEYW - MDW
1 stop5h 16mDelta
Deal found 1/2$335

Find 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 January 4, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$285
(Kiwi.com)

One-way from

$125
(Kiwi.com)

Popular in

November

Cheapest in

July

Average price

$483
Provider with most accurate pricing for Chicago Midway-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Key West flights.
Search Deals
From Chicago Midway to Key West
Search Deals
One-way flight from Chicago Midway to Key West
Search Deals
Highest demand for flights based on searches. 38% potential increase in price ($374 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease ($70 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 4, 2026.
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 3/4

12:45 pm-7:42 pm

1 stop5h 57m

Key West

Tue 3/10

6:25 pm-10:31 pm

1 stop5h 06m

$294

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 3/30

12:47 pm-7:41 pm

1 stop5h 54m

Key West

Tue 4/7

6:25 pm-10:31 pm

1 stop5h 06m

$294

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 2/21

11:06 am-7:42 pm

1 stop7h 36m

Key West

Wed 2/25

5:56 pm-10:31 pm

1 stop5h 35m

$294

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 2/1

12:46 pm-7:40 pm

1 stop5h 54m

Key West

Thu 2/26

5:56 pm-10:31 pm

1 stop5h 35m

$334

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 2/21

11:06 am-7:42 pm

1 stop7h 36m

Key West

Tue 2/24

5:56 pm-10:33 pm

1 stop5h 37m

$349

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 1/10

11:21 am-7:40 pm

1 stop7h 19m

Key West

Tue 1/13

6:06 pm-10:07 pm

1 stop5h 01m

$401

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 3/5

12:45 pm-7:42 pm

1 stop5h 57m

Key West

Mon 3/9

6:25 pm-10:31 pm

1 stop5h 06m

$429

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 2/20

1:26 pm-10:59 am

2 stops20h 33m

Key West

Thu 2/26

5:56 pm-10:31 pm

1 stop5h 35m

$436

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 2/24

12:45 pm-7:42 pm

1 stop5h 57m

Key West

Sat 2/28

5:56 pm-10:31 pm

1 stop5h 35m

$454

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 2/3

12:46 pm-7:40 pm

1 stop5h 54m

Key West

Mon 2/9

6:06 pm-10:22 pm

1 stop5h 16m

$454

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/4

Showing 1-10 of 20 results
1
2

Compare providers for flights from Midway to Key West

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 Midway to Key West in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*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 Chicago Midway Airport-Key West flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Key West flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Key West flights, Cheapflights users trust eDreams the most. eDreams 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 Chicago Midway Airport-Key West 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 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Key West (average of $287). Flying from Chicago Midway Airport to Key West in October is currently the most expensive (average of $998). 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 January 4, 2026.
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
7.9
Good
8,017 reviews

Crew

8.5

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Entertainment

7.8

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
7.9
Good
8,017 reviews
Delta
7.9
Good
8,017 reviews

Crew

8.5

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Entertainment

7.8

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 5h 57m. 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 $262. Users have found that Delta is 55% 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Key West (average of $287). Flying from Chicago Midway Airport to Key West in October is currently the most expensive (average of $998). 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 January 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$262Average$434FlexibilityNo cancel feeOn-timeN/A

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