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Florida Keys

$58+ Cheap flights from Midway (MDW) to Florida Keys

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 11/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
1 adult, Economy
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Find flight deals from Midway to Florida Keys

Cheapest flights from Midway to Florida Keys
Explore the most affordable flight options available from Midway to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 12, 2025.

This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/132:59 pmMDW - MIA
Nonstop3h 10mFrontier
Sat 12/2010:19 pmMIA - MDW
1 stop24h 53mFrontier
Deal found 11/9$113
This CheapOair deal was found by Cheapflights users on 11/11. 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.
Sun 12/142:59 pmMDW - MIA
Nonstop3h 10mFrontier
Sat 12/205:30 amMIA - MDW
1 stop8h 51mFrontier
Deal found 11/11$114
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/142:59 pmMDW - MIA
Nonstop3h 10mFrontier
Wed 12/2412:10 pmMIA - MDW
Nonstop3h 27mFrontier
Deal found 11/10$115
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/72:59 pmMDW - MIA
Nonstop3h 10mFrontier
Fri 12/127:09 pmMIA - MDW
1 stop27h 13mFrontier
Deal found 11/9$116
This CheapOair deal was found by Cheapflights users on 11/11. 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.
Sat 12/132:59 pmMDW - MIA
Nonstop3h 10mFrontier
Sun 12/146:00 amMIA - MDW
1 stop30h 08mFrontier
Deal found 11/11$117
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.
Sun 11/2312:25 pmMDW - MIA
1 stop7h 07mFrontier
Wed 11/262:44 pmMIA - MDW
Nonstop3h 13mFrontier
Deal found 11/9$120
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2412:25 pmMDW - MIA
1 stop7h 05mFrontier
Wed 11/262:44 pmMIA - MDW
Nonstop3h 13mFrontier
Deal found 11/9$121
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:42 pmMDW - MIA
1 stop10h 51mFrontier
Sat 12/206:59 amMIA - MDW
Nonstop3h 20mFrontier
Deal found 11/9$122
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 11/295:57 pmMDW - MIA
Nonstop3h 06mFrontier
Thu 12/47:26 pmMIA - MDW
Nonstop3h 27mFrontier
Deal found 11/8$123
This Frontier deal was found by Cheapflights users on 11/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:42 pmMDW - MIA
1 stop10h 51mFrontier
Mon 12/155:30 amMIA - MDW
1 stop5h 22mFrontier
Deal found 11/11$124
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/72:59 pmMDW - MIA
Nonstop3h 10mMultiple Airlines
Thu 12/119:59 pmMIA - MDW
1 stop24h 29mMultiple Airlines
Deal found 11/9$125
This CheapOair deal was found by Cheapflights users on 11/11. 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.
Wed 12/246:12 amMDW - MIA
1 stop12h 18mFrontier
Wed 12/3112:10 pmMIA - MDW
Nonstop3h 27mFrontier
Deal found 11/11$126

Cheap flight deals from Midway to Florida Keys

Keep the following information in mind while searching for Midway to Florida Keys flight deals. Data was last updated November 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$113
(CheapOair)

One-way from

$58
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$311
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
Search Deals
From Chicago Midway to Florida Keys
Search Deals
One-way flight from Chicago Midway to Florida Keys
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Florida Keys 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 12, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Florida Keys that are best for you.

Fly from

Midway

Fly to

Florida Keys

Route

Depart

Return

Price

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 1/27

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Thu 1/29

6:55 am-11:15 am

1 stop5h 20m

$167

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 1/29

3:15 pm-10:00 pm

1 stop5h 45m

Miami

Sat 2/7

7:35 am-11:35 am

1 stop5h 00m

$177

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 11/24

6:00 am-1:02 pm

1 stop6h 02m

Miami

Thu 12/4

4:55 pm-11:47 pm

1 stop7h 52m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 12/2

5:13 pm-12:46 am

1 stop6h 33m

Miami

Wed 12/3

8:10 am-12:34 pm

1 stop5h 24m

$228

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 1/24

6:40 am-2:50 pm

1 stop7h 10m

Miami

Fri 1/30

7:15 am-1:55 pm

2 stops7h 40m

$243

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 1/20

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Mon 1/26

7:15 am-2:55 pm

1 stop8h 40m

$270

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 12/6

1:14 pm-9:50 pm

1 stop7h 36m

Miami

Thu 12/18

8:05 am-11:58 am

1 stop4h 53m

$273

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 2/6

1:35 pm-10:25 pm

2 stops7h 50m

Miami

Sat 2/14

7:45 am-5:00 pm

2 stops10h 15m

$293

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 12/9

2:25 pm-9:50 pm

2 stops6h 25m

Miami

Thu 12/11

9:30 am-5:00 pm

2 stops8h 30m

$297

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 11/25

12:47 pm-7:53 pm

1 stop6h 06m

Key West

Tue 12/2

6:10 pm-11:47 pm

1 stop6h 37m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 38 results
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Best time to book a flight from Midway to Florida Keys

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

What is the cheapest month to book a flight from Chicago Midway Airport to Florida Keys?

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida Keys (average of $211). Flying from Chicago Midway Airport to Florida Keys in October is currently the most expensive (average of $998). 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.

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. 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 Florida Keys. Reviews last updated November 12, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Chicago Midway Airport to Florida Keys. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
7.9
Good
8,008 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
9,015 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Spirit Airlines
6.3
Okay
8,137 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.8
Fair
3,113 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Midway to Florida Keys. 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 Chicago Midway Airport to Florida Keys?

    A quick flight from Chicago Midway Airport to Florida Keys can take about 3h. Southwest provides one of the quickest options available for as low as $167. Chicago Midway Airport and Florida Keys are separated by a distance of 1183 mi. This flight may include one or multiple stops.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida Keys (average of $211). Flying from Chicago Midway Airport to Florida Keys in October is currently the most expensive (average of $998). 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

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Alternative routes for Midway to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Midway to Florida Keys

Discover the top airline that operate flights from Midway to Florida Keys. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$262Average$538FlexibilityNo cancel feeOn-timeN/A

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