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Midway

$64+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MDW
Jan 12 — Jan 191
Mon 1/12
Mon 1/19
1 adult, Economy
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Cheap 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 December 13, 2025.

This CheapOair deal was found by Cheapflights users on 12/10. 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
Sat 1/32:24 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 12/10$105
This Kiwi.com deal was found by Cheapflights users on 12/12. 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.
Tue 12/309:59 pmMIA - MDW
1 stop25h 13mMultiple Airlines
Mon 1/56:15 amMDW - MIA
Nonstop3h 17mMultiple Airlines
Deal found 12/12$125
This CheapOair deal was found by Cheapflights users on 12/12. 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 12/3112:10 pmMIA - MDW
Nonstop3h 27mFrontier
Mon 1/197:20 pmMDW - MIA
Nonstop3h 05mFrontier
Deal found 12/12$129
This Super.com deal was found by Cheapflights users on 12/11. 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.
Wed 12/2412:10 pmMIA - MDW
Nonstop3h 27mFrontier
Wed 12/313:32 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 12/11$137
This Frontier deal was found by Cheapflights users on 12/13. 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.
Wed 12/3112:10 pmMIA - MDW
Nonstop3h 27mFrontier
Wed 1/73:01 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 12/13$140
This CheapOair deal was found by Cheapflights users on 12/11. 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
Sun 12/142:59 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 12/11$149
This Super.com deal was found by Cheapflights users on 12/11. 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.
Sat 12/138:09 pmMIA - MDW
Nonstop3h 21mFrontier
Sun 12/142:59 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 12/11$157
This WAYA deal was found by Cheapflights users on 12/11. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2412:10 pmMIA - MDW
Nonstop3h 27mMultiple Airlines
Wed 12/316:12 amMDW - MIA
1 stop5h 54mMultiple Airlines
Deal found 12/11$161
This Priceline deal was found by Cheapflights users on 12/11. 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.
Sat 12/206:59 amMIA - MDW
Nonstop3h 20mFrontier
Wed 12/313:32 pmMDW - MIA
Nonstop3h 10mFrontier
Deal found 12/11$168
This Kiwi.com deal was found by Cheapflights users on 12/11. 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.
Sun 12/289:59 pmMIA - MDW
1 stop25h 13mMultiple Airlines
Mon 1/56:15 amMDW - MIA
Nonstop3h 17mMultiple Airlines
Deal found 12/11$178
This Priceline deal was found by Cheapflights users on 12/12. 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.
Sat 12/138:09 pmMIA - MDW
Nonstop3h 21mFrontier
Mon 12/1512:35 pmMDW - MIA
1 stop9h 43mFrontier
Deal found 12/12$181
This Delta deal was found by Cheapflights users on 12/11. 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.
Mon 12/297:25 amEYW - MDW
1 stop5h 33mDelta
Mon 1/1211:21 amMDW - EYW
1 stop7h 19mDelta
Deal found 12/11$299

Find 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 December 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$86
(CheapOair)

One-way from

$64
(Frontier)
Provider with most accurate pricing for Key West-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Chicago (CHI) flights.
Search Deals
From Florida Keys to Chicago Midway
Search Deals
One-way flight from Florida Keys to Chicago Midway
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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 December 13, 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 1/17

6:30 am-8:40 am

Nonstop3h 10m

Chicago Midway

Mon 1/19

9:40 am-1:45 pm

Nonstop3h 05m

$168

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 1/9

5:50 am-10:27 am

1 stop5h 37m

Chicago Midway

Sun 1/11

1:28 pm-9:37 pm

1 stop7h 09m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 1/8

2:35 pm-4:50 pm

Nonstop3h 15m

Chicago Midway

Sun 1/11

9:40 am-1:45 pm

Nonstop3h 05m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 1/16

5:50 am-10:27 am

1 stop5h 37m

Chicago Midway

Mon 1/19

1:26 pm-10:03 pm

1 stop7h 37m

$217

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 1/31

6:30 am-8:40 am

Nonstop3h 10m

Chicago Midway

Sat 2/7

8:25 am-4:25 pm

1 stop7h 00m

$218

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 1/23

2:35 pm-4:50 pm

Nonstop3h 15m

Chicago Midway

Sun 1/25

9:35 am-3:50 pm

1 stop5h 15m

$218

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 1/31

6:30 am-8:40 am

Nonstop3h 10m

Chicago Midway

Thu 2/5

9:45 am-3:50 pm

1 stop5h 05m

$218

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 2/20

7:15 am-11:59 am

1 stop5h 44m

Chicago Midway

Sun 2/22

9:34 am-5:29 pm

1 stop6h 55m

$243

Key WestChicago

EYW - MDW

EYWMDW

Key West

Mon 12/29

7:25 am-11:58 am

1 stop5h 33m

Chicago Midway

Mon 1/12

6:45 am-1:48 pm

1 stop6h 03m

$299

Key WestChicago

EYW - MDW

EYWMDW

Key West

Thu 4/9

6:25 pm-10:29 pm

1 stop5h 04m

Chicago Midway

Mon 4/13

10:35 am-5:12 pm

1 stop5h 37m

$334

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/12

Showing 1-10 of 27 results
1
2
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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 December 13, 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
7.9
Good
4,253 reviews

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

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
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

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
3,083 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

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 Southwest and Delta fly from Florida Keys to Chicago Midway Airport in about 3h 10m. The time it takes to get you to your destination can typically vary by up to 2h 27m. 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.

  • 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 $39 on Frontier. Other airlines that offer cheap prices include Southwest from $79 and Delta from $108 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.

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
Merrillville
Hammond
Porter
Benton Harbor

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