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$68+ 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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Dec 11 — Dec 181
Thu 12/11
Thu 12/18
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 November 11, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$100
(Kiwi.com)

One-way from

$68
(Kiwi.com)
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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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 November 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/8. 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.
Mon 12/87:09 pmMIA - MDW
1 stop14h 37mFrontier
Sat 12/132:59 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 11/8$100
This CheapOair deal was found by Cheapflights users on 11/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:26 pmMIA - MDW
Nonstop3h 27mFrontier
Thu 12/186:33 pmMDW - MIA
1 stop5h 14mFrontier
Deal found 11/10$101
This CheapOair deal was found by Cheapflights users on 11/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:26 pmMIA - MDW
Nonstop3h 27mFrontier
Fri 12/128:42 pmMDW - MIA
1 stop10h 51mFrontier
Deal found 11/10$102
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Thu 12/46:05 amMIA - MDW
1 stop13h 03mMultiple Airlines
Sun 12/72:59 pmMDW - MIA
Nonstop3h 10mMultiple Airlines
Deal found 11/10$103
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Wed 12/109:03 pmMIA - MDW
1 stop16h 58mFrontier
Sun 12/142:59 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 11/10$105
This Kissandfly.com deal was found by Cheapflights users on 11/10. 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.
Thu 12/47:26 pmMIA - MDW
Nonstop3h 27mFrontier
Sun 12/77:44 amMDW - MIA
1 stop11h 03mFrontier
Deal found 11/10$106
This CheapOair deal was found by Cheapflights users on 11/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/222:44 pmMIA - MDW
Nonstop3h 13mFrontier
Wed 11/265:57 pmMDW - MIA
Nonstop3h 06mFrontier
Deal found 11/8$108
This Frontier deal was found by Cheapflights users on 11/8. 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.
Sat 12/69:38 amMIA - MDW
1 stop5h 21mFrontier
Mon 12/1512:35 pmMDW - MIA
1 stop9h 43mFrontier
Deal found 11/8$110
This CheapOair deal was found by Cheapflights users on 11/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2412:10 pmMIA - MDW
Nonstop3h 27mFrontier
Mon 12/296:15 amMDW - MIA
Nonstop3h 17mFrontier
Deal found 11/10$114
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Sat 12/139:38 amMIA - MDW
1 stop12h 44mFrontier
Sun 12/142:59 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 11/10$115
This Super.com deal was found by Cheapflights users on 11/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/244:35 pmMIA - MDW
1 stop6h 42mFrontier
Wed 11/265:57 pmMDW - MIA
Nonstop3h 06mFrontier
Deal found 11/9$120
This CheapOair deal was found by Cheapflights users on 11/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/262:44 pmMIA - MDW
Nonstop3h 13mFrontier
Thu 11/276:05 amMDW - MIA
1 stop10h 04mFrontier
Deal found 11/9$121

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 November 11, 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

Sat 12/6

9:38 am-1:59 pm

1 stop5h 21m

Chicago Midway

Sat 12/13

6:00 am-3:39 pm

1 stop8h 39m

$110

MiamiChicago

MIA - MDW

MIAMDW

Miami

Mon 12/22

11:42 am-2:05 pm

Nonstop3h 23m

Chicago Midway

Mon 12/29

6:15 am-10:32 am

Nonstop3h 17m

$168

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 1/8

6:55 am-12:30 pm

2 stops6h 35m

Chicago Midway

Mon 1/12

5:30 pm-9:30 pm

Nonstop3h 00m

$172

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 12/12

6:20 am-8:35 am

Nonstop3h 15m

Chicago Midway

Mon 12/15

6:40 am-4:10 pm

1 stop8h 30m

$187

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 12/12

6:20 am-8:35 am

Nonstop3h 15m

Chicago Midway

Sun 12/14

9:10 am-4:30 pm

1 stop6h 20m

$187

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 12/25

8:55 am-9:58 pm

1 stop14h 03m

Chicago Midway

Thu 1/1

3:10 pm-12:30 pm

1 stop20h 20m

$188

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 12/11

8:55 am-9:58 pm

1 stop14h 03m

Chicago Midway

Sun 12/14

6:37 pm-8:15 am

1 stop12h 38m

$208

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 12/13

6:05 am-3:20 pm

2 stops10h 15m

Chicago Midway

Mon 12/15

9:00 am-1:05 pm

Nonstop3h 05m

$212

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 1/7

6:00 am-10:34 am

1 stop5h 34m

Chicago Midway

Sun 1/11

9:34 am-5:48 pm

1 stop7h 14m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

Tue 12/9

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Mon 12/15

5:29 pm-12:46 am

1 stop6h 17m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 41 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 November 11, 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
4,235 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

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
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

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
3,113 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

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 5h 18m. The time it takes to get you to your destination can typically vary by up to 1h 17m. The distance from Florida Keys to Chicago Midway Airport is about 1238 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.

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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Alternative routes for Florida Keys to Midway

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