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$131+ Cheap flights from Key West (EYW) to Midway (MDW)

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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Key West to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Midway (MDW). 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$434
(Delta)

One-way from

$131
(Trip.com)

Popular in

February

Cheapest in

August

Average price

$536
Provider with most accurate pricing for Key West-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Chicago Midway flights.
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From Key West to Chicago Midway
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One-way flight from Key West to Chicago Midway
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($55 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 February 2025
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Find flight deals from Key West to Midway

Cheapest flights from Key West to Midway
Explore the most affordable flight options available from Key West to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Delta deal was found by Cheapflights users on 2/19. 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 3/77:00 amEYW - MDW
1 stop5h 59mDelta
Tue 3/116:00 amMDW - EYW
1 stop4h 35mDelta
Deal found 2/19$434

Find flights from Key West to Midway within your budget

Customize your flight search to find flights from Key West to Midway 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 February 20, 2025.

Fly from

Key West

Fly to

Midway

Route

Depart

Return

Price

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 3/7

7:00 am-11:59 am

1 stop5h 59m

Chicago Midway

Tue 3/11

6:00 am-11:35 am

1 stop4h 35m

$434

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 4/15

10:00 am-4:08 pm

1 stop7h 08m

$131

Key WestChicago

EYW - MDW

EYWMDW

Key West

Tue 4/22

7:00 am-12:03 pm

1 stop6h 03m

$314

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Compare providers for flights from Key West to Midway

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 Key West to Midway in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 Key West-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Key West-Chicago Midway Airport 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 Key West-Chicago Midway Airport 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 Key West to Midway

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

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

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated February 20, 2025.
Delta
8.0
Very good
8,227 reviews

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Reviews

1 / 20

2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
8,227 reviews
Delta
8.0
Very good
8,227 reviews

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

8.0

Entertainment

7.9

Reviews

1 / 20

2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

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

    If you book a flight to Chicago Midway from Key West, you will be flying from Key West, which is the city’s only airport. Key West (EYW) is located 2.6 mi from the center of Key West. There are 0 flights from Key West to Chicago Midway per day from 0 different airlines.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Key West to Chicago Midway Airport (average of $160). Flying from Key West to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Key West?

Book flights to Key West if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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