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$253+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Jun 13 — Jun 201
Fri 6/13
Fri 6/20
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 June 8, 2025.

Round-trip from

$324
(Delta)

One-way from

$253
(Delta)

Popular in

February

Cheapest in

September

Average price

$556
From Chicago Midway to Key West
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One-way flight from Chicago Midway to Key West
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High demand for flights, 3% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 8, 2025.

This Delta deal was found by Cheapflights users on 6/8. 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 8/212:43 pmMDW - EYW
1 stop6h 06mDelta
Thu 8/72:03 pmEYW - MDW
1 stop4h 59mDelta
Deal found 6/8$324
This Trip.com deal was found by Cheapflights users on 6/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1511:39 amMDW - EYW
2 stops19h 21mMultiple Airlines
Tue 7/222:45 pmEYW - MDW
2 stops29h 51mMultiple Airlines
Deal found 6/6$341
This Mytrip deal was found by Cheapflights users on 6/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1311:37 amMDW - EYW
2 stops27h 59mAllegiant Air
Thu 7/174:20 pmEYW - MDW
1 stop18h 21mAllegiant Air
Deal found 6/7$382

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 June 8, 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

Sat 8/2

12:43 pm-7:49 pm

1 stop6h 06m

Key West

Thu 8/7

2:03 pm-6:02 pm

1 stop4h 59m

$324

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 7/15

11:39 am-8:00 am

2 stops19h 21m

Key West

Tue 7/22

2:45 pm-7:36 pm

2 stops29h 51m

$341

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 7/13

11:37 am-4:36 pm

2 stops27h 59m

Key West

Thu 7/17

4:20 pm-9:41 am

1 stop18h 21m

$382

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 7/15

6:00 am-1:08 pm

1 stop6h 08m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/7

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.

Rainfall in Key West by month

Plan your trip to Key West by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

Temperature in Key West by month

Plan your trip to Key West by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

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 June 8, 2025.
Delta
8.0
Very good
7,954 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

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
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

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.
Allegiant Air
7.3
Good
728 reviews
Delta
8.0
Very good
7,954 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

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 are the cheapest airlines flying from Chicago Midway Airport to Key West round-trip?

    Flying on Delta is currently your cheapest option to Key West, with prices starting at $324. Another option worth looking into is Allegiant Air, starting at $382 round trip. Users have found that Delta is 30% 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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Alternative routes for Midway to Key West

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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 June 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$438FlexibilityNo cancel feeOn-timeN/A

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