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$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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Jan 20 — Jan 271
Mon 1/20
Mon 1/27
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 January 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$279
(Delta)

One-way from

$174
(Trip.com)

Popular in

May

Cheapest in

January

Average price

$324
Provider with most accurate pricing for Chicago Midway-Key West flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Key West flights.
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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, 31% potential price rise
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Best time to find cheap flights, 9% potential price drop
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Average for round-trip flights in January 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 January 15, 2025.

This Delta deal was found by Cheapflights users on 1/13. 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.
Wed 2/2612:44 pmMDW - EYW
1 stop6h 27mDelta
Tue 3/46:14 pmEYW - MDW
1 stop5h 06mDelta
Deal found 1/13$279
This Trip.com deal was found by Cheapflights users on 1/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/105:15 amMDW - EYW
1 stop11h 00mMultiple Airlines
Mon 4/142:00 pmEYW - MDW
1 stop6h 46mMultiple Airlines
Deal found 1/15$338
This Kissandfly.com deal was found by Cheapflights users on 1/14. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/110:43 amMDW - EYW
1 stop7h 13mFrontier
Sat 3/86:14 pmEYW - MDW
1 stop5h 06mFrontier
Deal found 1/14$586

Find flights from Midway to Key West within your budget

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 15, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 2/26

12:44 pm-8:11 pm

1 stop6h 27m

Key West

Tue 3/4

6:14 pm-10:20 pm

1 stop5h 06m

$279

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 4/10

5:15 am-5:15 pm

1 stop11h 00m

Key West

Mon 4/14

2:00 pm-7:46 pm

1 stop6h 46m

$338

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 3/1

10:43 am-6:56 pm

1 stop7h 13m

Key West

Sat 3/8

6:14 pm-10:20 pm

1 stop5h 06m

$586

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 4/23

1:05 pm-8:29 pm

1 stop6h 24m

$140

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 4/13

5:15 am-5:15 pm

1 stop11h 00m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

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 Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Key West flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

Travel insights for flights from Midway to Key West

Get recent, data-driven insights about flights from Midway to Key West including ideal travel times, pricing trends, and more.

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 January 15, 2025.
Delta
8.0
Very good
8,511 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 10

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
8,511 reviews
Delta
8.0
Very good
8,511 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 10

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.

Frontier
6.1
Okay
3,433 reviews
Delta
8.0
Very good
8,511 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 10

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 $279. Another option worth looking into is Frontier, starting at $586 round trip. Users have found that Delta is 46% 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 $531). 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.

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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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$517FlexibilityNo cancel feeOn-timeN/A
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