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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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Aug 11 — Aug 181
Mon 8/11
Mon 8/18
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 August 6, 2025.

Round-trip from

$131
(Frontier)

One-way from

$69
(Southwest)

Popular in

March

Cheapest in

June

Average price

$328
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 ($79 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 August 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 August 6, 2025.

This Frontier deal was found by Cheapflights users on 8/6. 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 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
Mon 10/1310:03 pmMDW - MIA
Nonstop3h 00mFrontier
Deal found 8/6$131
This Southwest deal was found by Cheapflights users on 8/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1912:35 pmMIA - MDW
Nonstop3h 10mSouthwest
Mon 9/222:10 pmMDW - MIA
Nonstop3h 00mSouthwest
Deal found 8/6$132
This Southwest deal was found by Cheapflights users on 8/5. 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.
Sat 9/66:05 amMIA - MDW
1 stop6h 05mSouthwest
Mon 9/82:10 pmMDW - MIA
Nonstop3h 00mSouthwest
Deal found 8/5$137
This Southwest deal was found by Cheapflights users on 8/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/39:00 amMIA - MDW
1 stop9h 10mSouthwest
Wed 9/108:35 amMDW - MIA
1 stop7h 05mSouthwest
Deal found 8/4$146
This Southwest deal was found by Cheapflights users on 8/5. 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.
Thu 9/184:40 pmMIA - MDW
1 stop7h 10mSouthwest
Mon 9/226:30 amMDW - MIA
1 stop8h 15mSouthwest
Deal found 8/5$152
This Southwest deal was found by Cheapflights users on 8/5. 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.
Wed 9/36:55 amMIA - MDW
1 stop5h 55mSouthwest
Tue 9/98:35 amMDW - MIA
1 stop7h 05mSouthwest
Deal found 8/5$153
This Southwest deal was found by Cheapflights users on 8/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/3011:40 amMIA - MDW
2 stops8h 30mSouthwest
Tue 10/143:10 pmMDW - MIA
1 stop5h 45mSouthwest
Deal found 8/4$157
This Southwest deal was found by Cheapflights users on 8/5. 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.
Tue 8/269:00 amMIA - MDW
1 stop9h 10mSouthwest
Wed 9/242:05 pmMDW - MIA
1 stop5h 35mSouthwest
Deal found 8/5$158
This Southwest deal was found by Cheapflights users on 8/5. 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.
Tue 8/267:10 amMIA - MDW
1 stop5h 35mSouthwest
Wed 8/278:35 amMDW - MIA
1 stop7h 05mSouthwest
Deal found 8/5$159
This Delta deal was found by Cheapflights users on 8/5. 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.
Thu 8/212:00 pmEYW - MDW
1 stop4h 47mDelta
Mon 8/256:00 amMDW - EYW
1 stop6h 05mDelta
Deal found 8/5$309
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/72:03 pmEYW - MDW
1 stop4h 44mDelta
Tue 9/910:31 amMDW - EYW
1 stop5h 54mDelta
Deal found 8/6$363
This Delta deal was found by Cheapflights users on 8/5. 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 12/196:00 pmEYW - MDW
1 stop4h 44mDelta
Mon 12/2212:10 pmMDW - EYW
1 stop6h 34mDelta
Deal found 8/5$464

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 August 6, 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

Thu 10/9

6:53 pm-9:08 pm

Nonstop3h 15m

Chicago Midway

Mon 10/13

10:03 pm-2:03 am

Nonstop3h 00m

$131

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 9/19

12:35 pm-2:45 pm

Nonstop3h 10m

Chicago Midway

Mon 9/22

2:10 pm-6:10 pm

Nonstop3h 00m

$132

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 9/6

6:05 am-11:10 am

1 stop6h 05m

Chicago Midway

Mon 9/8

2:10 pm-6:10 pm

Nonstop3h 00m

$137

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 9/3

6:55 am-11:50 am

1 stop5h 55m

Chicago Midway

Thu 9/4

5:25 am-3:15 pm

1 stop8h 50m

$146

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 9/18

4:40 pm-10:50 pm

1 stop7h 10m

Chicago Midway

Mon 9/22

6:30 am-3:45 pm

1 stop8h 15m

$152

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 9/3

6:55 am-11:50 am

1 stop5h 55m

Chicago Midway

Tue 9/9

8:35 am-4:40 pm

1 stop7h 05m

$153

MiamiChicago

MIA - MDW

MIAMDW

Miami

Tue 9/30

11:40 am-7:10 pm

2 stops8h 30m

Chicago Midway

Tue 10/14

3:10 pm-9:55 pm

1 stop5h 45m

$157

MiamiChicago

MIA - MDW

MIAMDW

Miami

Tue 8/26

9:00 am-5:10 pm

1 stop9h 10m

Chicago Midway

Wed 9/24

2:05 pm-8:40 pm

1 stop5h 35m

$158

MiamiChicago

MIA - MDW

MIAMDW

Miami

Tue 8/26

7:10 am-11:45 am

1 stop5h 35m

Chicago Midway

Wed 8/27

8:35 am-4:40 pm

1 stop7h 05m

$159

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 8/21

2:00 pm-5:47 pm

1 stop4h 47m

Chicago Midway

Mon 8/25

6:00 am-1:05 pm

1 stop6h 05m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/5

Showing 1-10 of 34 results
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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
No data available for this route at this time. Please check back soon.

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 August 6, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Frontier from Florida Keys to Chicago Midway Airport by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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
7,985 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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
3,231 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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.

  • 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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