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$57+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
oct. 25 — nov. 11
sáb. 10/25
sáb. 11/1
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 septiembre 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$106
(Cheapflightsfares)

One-way from

$57
(Cheapflightsfares)

Popular in

March

Cheapest in

June

Average price

$288
Provider with most accurate pricing for Key West-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Key West-Chicago (CHI) flights.
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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. 20% potential increase in price ($91 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 25, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/109:10 amMIA - MDW
Nonstop3h 17mFrontier
lun. 10/134:24 pmMDW - MIA
Nonstop3h 02mFrontier
Deal found 9/24$106
This Frontier deal was found by Cheapflights users on 9/24. 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.
sáb. 11/17:05 pmMIA - MDW
Nonstop3h 17mFrontier
mar. 12/98:00 amMDW - MIA
Nonstop3h 15mFrontier
Deal found 9/24$116
This Priceline deal was found by Cheapflights users on 9/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/2510:34 amMIA - MDW
1 stop7h 39mFrontier
lun. 10/2712:17 pmMDW - MIA
Nonstop3h 01mFrontier
Deal found 9/25$118
This Booking.com deal was found by Cheapflights users on 9/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/17:05 pmMIA - MDW
Nonstop3h 17mFrontier
dom. 11/28:32 amMDW - MIA
1 stop11h 50mFrontier
Deal found 9/24$119
This Priceline deal was found by Cheapflights users on 9/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/166:57 pmMIA - MDW
1 stop5h 49mFrontier
lun. 10/2010:33 amMDW - MIA
Nonstop3h 00mFrontier
Deal found 9/24$121
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/177:20 amMIA - MDW
Nonstop3h 13mFrontier
lun. 10/275:20 pmMDW - MIA
1 stop6h 30mFrontier
Deal found 9/24$125
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/1810:34 amMIA - MDW
1 stop7h 39mFrontier
lun. 10/2712:17 pmMDW - MIA
Nonstop3h 01mFrontier
Deal found 9/24$126
This Booking.com deal was found by Cheapflights users on 9/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/109:10 amMIA - MDW
Nonstop3h 17mFrontier
mar. 10/148:05 amMDW - MIA
1 stop5h 27mFrontier
Deal found 9/24$128
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/177:20 amMIA - MDW
Nonstop3h 13mFrontier
sáb. 10/2510:00 amMDW - MIA
1 stop12h 43mFrontier
Deal found 9/24$130
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/108:55 amEYW - MDW
1 stop8h 25mMultiple Airlines
dom. 10/195:20 amMDW - EYW
1 stop9h 44mMultiple Airlines
Deal found 9/25$264
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/108:55 amEYW - MDW
1 stop8h 25mMultiple Airlines
vie. 10/1712:13 pmMDW - EYW
2 stops19h 49mMultiple Airlines
Deal found 9/24$284
This Delta deal was found by Cheapflights users on 9/25. 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.
lun. 11/246:18 pmEYW - MDW
1 stop6h 22mDelta
sáb. 11/296:00 amMDW - EYW
1 stop4h 31mDelta
Deal found 9/25$289

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 septiembre 25, 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

jue. 10/23

6:57 pm-11:46 pm

1 stop5h 49m

Chicago Midway

lun. 10/27

12:17 pm-4:18 pm

Nonstop3h 01m

$118

MiamiChicago

MIA - MDW

MIAMDW

Miami

sáb. 10/11

7:00 am-4:09 pm

1 stop10h 09m

Chicago Midway

mié. 10/15

8:05 am-2:33 pm

1 stop5h 28m

$144

MiamiChicago

MIA - MDW

MIAMDW

Miami

vie. 10/10

9:10 am-11:27 am

Nonstop3h 17m

Chicago Midway

mar. 10/14

8:05 am-2:32 pm

1 stop5h 27m

$155

MiamiChicago

MIA - MDW

MIAMDW

Miami

jue. 11/6

6:20 am-8:35 am

Nonstop3h 15m

Chicago Midway

mar. 11/18

9:00 am-1:05 pm

Nonstop3h 05m

$157

MiamiChicago

MIA - MDW

MIAMDW

Miami

sáb. 11/1

6:00 am-9:45 am

1 stop4h 45m

Chicago Midway

mar. 11/4

9:35 am-4:30 pm

1 stop5h 55m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

mar. 10/21

12:09 pm-4:09 pm

1 stop5h 00m

Chicago Midway

mié. 10/22

12:48 pm-6:34 pm

1 stop4h 46m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

vie. 12/5

8:05 am-12:34 pm

1 stop5h 29m

Chicago Midway

lun. 12/8

6:00 am-1:06 pm

1 stop6h 06m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

jue. 10/16

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

lun. 10/20

9:35 am-4:30 pm

1 stop5h 55m

$217

Key WestChicago

EYW - MDW

EYWMDW

Key West

lun. 11/24

6:18 pm-11:40 pm

1 stop6h 22m

Chicago Midway

sáb. 11/29

6:00 am-11:31 am

1 stop4h 31m

$289

Key WestChicago

EYW - MDW

EYWMDW

Key West

sáb. 10/11

6:17 pm-10:14 pm

1 stop4h 57m

Chicago Midway

mar. 10/14

6:00 am-11:27 am

1 stop4h 27m

$435

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/24

Showing 1-10 of 33 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 septiembre 25, 2025.
Get a feel of what it's like to fly with Southwest 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
4,246 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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
5.8
Fair
3,162 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

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.

  • How long is the flight from Florida Keys to Chicago Midway Airport?

    Airlines like Frontier, Southwest, and Delta fly from Florida Keys to Chicago Midway Airport in about 3h 15m. The time it takes to get you to your destination can typically vary by up to 3h 07m. The distance from Florida Keys to Chicago Midway Airport is about 1183 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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
Chesterton

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