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$69+ Cheap flights from Florida Keys 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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
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Cheap flight deals from Florida Keys to Midway

Keep the following information in mind while searching for Florida Keys to Midway flight deals. Data was last updated June 18, 2025.

Round-trip from

$147
(Southwest)

One-way from

$69
(Southwest)

Popular in

March

Cheapest in

June

Average price

$268
From Florida Keys to Chicago Midway
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One-way flight from Florida Keys to Chicago Midway
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Highest demand for flights based on searches. 17% potential increase in price ($78 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% 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 Florida Keys to Midway

Cheapest flights from Florida Keys to Midway
Explore the most affordable flight options available from Florida Keys to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2025.

This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/217:30 amMIA - MDW
Nonstop3h 05mSouthwest
Mon 9/227:15 amMDW - MIA
1 stop8h 05mSouthwest
Deal found 6/17$147
This Frontier deal was found by Cheapflights users on 6/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/96:53 pmMIA - MDW
Nonstop3h 15mFrontier
Sun 10/1210:03 pmMDW - MIA
Nonstop3h 00mFrontier
Deal found 6/17$151
This Delta deal was found by Cheapflights users on 6/17. 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 7/2512:46 pmMIA - MDW
1 stop6h 54mDelta
Tue 7/2910:30 amMDW - MIA
1 stop5h 23mDelta
Deal found 6/17$217
This Delta deal was found by Cheapflights users on 6/17. 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 7/27:10 amEYW - MDW
1 stop5h 49mDelta
Wed 7/912:43 pmMDW - EYW
1 stop6h 06mDelta
Deal found 6/17$409

Cheapflights Fare Finder

Customize your flight search to find flights from Florida Keys 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 June 18, 2025.
Use the filters below to find and compare flights from Florida Keys to Chicago Midway Airport that are best for you.

Fly from

Florida Keys

Fly to

Midway

Route

Depart

Return

Price

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sun 9/21

7:30 am-9:35 am

Nonstop3h 05m

Chicago Midway

Mon 9/22

7:15 am-4:20 pm

1 stop8h 05m

$147

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 10/9

6:53 pm-9:08 pm

Nonstop3h 15m

Chicago Midway

Sun 10/12

10:03 pm-2:03 am

Nonstop3h 00m

$151

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 7/25

12:46 pm-6:40 pm

1 stop6h 54m

Chicago Midway

Tue 7/29

10:30 am-4:53 pm

1 stop5h 23m

$217

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 7/2

7:10 am-11:59 am

1 stop5h 49m

Chicago Midway

Wed 7/9

12:43 pm-7:49 pm

1 stop6h 06m

$409

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 8/21

12:35 pm-2:45 pm

Nonstop3h 10m

$69

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 10/9

6:53 pm-9:08 pm

Nonstop3h 15m

$96

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 7/31

12:46 pm-6:40 pm

1 stop6h 54m

$114

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 8/8

11:11 am-11:17 pm

1 stop13h 06m

$138

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 8/22

7:00 am-11:48 am

1 stop5h 48m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Best time to book a flight from Florida Keys to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Florida Keys 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 Florida Keys to Chicago Midway Airport

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 June 18, 2025.
Read through reviews of airlines operating flights from Florida Keys to Chicago, such as Southwest, Delta and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
8.0
Very good
7,964 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.9
Fair
3,299 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Florida Keys to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Florida Keys to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $69 on Southwest. Other airlines that offer cheap prices include Frontier from $96 and Delta from $114 one-way.

  • Can I find deals for flights from Florida Keys to Midway that include hotel bookings?

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

  • How can I find direct flights from Florida Keys to Midway?

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

  • Can I find deals for business class flights from Florida Keys to Midway?

    Yes. Cheapflights offers flight deals from Florida Keys 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 Florida Keys to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Florida Keys to Chicago Midway Airport (average of $160). Flying from Florida Keys 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 Florida Keys?

Book flights to Florida Keys if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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