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Florida Keys

$56+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
1 adult, Economy
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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 September 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$104
(Kiwi.com)

One-way from

$56
(CheapOair)

Popular in

March

Cheapest in

September

Average price

$232
Provider with most accurate pricing for Chicago (CHI)-Miami flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Miami flights.
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From Chicago Midway to Florida Keys
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One-way flight from Chicago Midway to Florida Keys
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Highest demand for flights based on searches. 6% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 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 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 September 25, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/23. 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 10/134:24 pmMDW - MIA
Nonstop3h 02mFrontier
Fri 10/177:20 amMIA - MDW
Nonstop3h 13mFrontier
Deal found 9/23$104
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:30 amMDW - MIA
Nonstop3h 17mFrontier
Tue 12/161:12 pmMIA - MDW
Nonstop3h 18mFrontier
Deal found 9/25$108
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 10/134:24 pmMDW - MIA
Nonstop3h 02mFrontier
Mon 10/207:20 amMIA - MDW
Nonstop3h 13mFrontier
Deal found 9/23$109
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.
Wed 10/158:05 amMDW - MIA
1 stop9h 40mFrontier
Fri 10/177:20 amMIA - MDW
Nonstop3h 13mFrontier
Deal found 9/24$116
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:25 amMDW - MIA
1 stop10h 29mFrontier
Fri 10/177:20 amMIA - MDW
Nonstop3h 13mFrontier
Deal found 9/25$117
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2412:11 pmMDW - MIA
1 stop27h 03mFrontier
Mon 10/279:00 amMIA - MDW
Nonstop3h 17mFrontier
Deal found 9/25$118
This CheapOair deal was found by Cheapflights users on 9/23. 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.
Fri 10/2412:18 pmMDW - MIA
Nonstop3h 01mFrontier
Sun 10/266:00 amMIA - MDW
1 stop30h 16mFrontier
Deal found 9/23$120
This CheapOair deal was found by Cheapflights users on 9/23. 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.
Mon 10/2010:33 amMDW - MIA
Nonstop3h 00mFrontier
Thu 10/236:57 pmMIA - MDW
1 stop5h 49mFrontier
Deal found 9/23$121
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.
Sat 11/82:05 pmMDW - MIA
Nonstop3h 00mFrontier
Mon 11/1010:30 amMIA - MDW
1 stop7h 45mFrontier
Deal found 9/24$122
This CheapOair deal was found by Cheapflights users on 9/23. 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 10/98:25 amMDW - MIA
1 stop10h 29mFrontier
Mon 10/139:26 pmMIA - MDW
Nonstop3h 20mFrontier
Deal found 9/23$123
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/128:25 amMDW - MIA
1 stop10h 34mFrontier
Fri 10/177:20 amMIA - MDW
Nonstop3h 13mFrontier
Deal found 9/24$125
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 10/209:45 amMDW - EYW
1 stop24h 20mMultiple Airlines
Mon 10/272:57 pmEYW - MDW
1 stop5h 37mMultiple Airlines
Deal found 9/23$224

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 September 25, 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 1/6

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Sat 1/10

6:30 am-8:40 am

Nonstop3h 10m

$179

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 1/7

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Wed 1/14

2:35 pm-4:50 pm

Nonstop3h 15m

$179

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 1/17

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Sat 1/24

6:30 am-8:40 am

Nonstop3h 10m

$179

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 10/25

4:23 pm-12:29 am

1 stop7h 06m

Miami

Tue 10/28

6:00 am-9:40 am

1 stop4h 40m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 11/18

12:47 pm-8:46 pm

1 stop6h 59m

Miami

Wed 12/3

6:30 pm-11:32 pm

1 stop6h 02m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 10/22

12:48 pm-6:34 pm

1 stop4h 46m

Miami

Wed 10/29

12:20 pm-6:25 pm

1 stop7h 05m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 10/22

5:30 am-4:50 pm

2 stops10h 20m

Miami

Wed 10/29

11:45 am-7:10 pm

2 stops8h 25m

$247

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 10/30

10:40 am-6:34 pm

1 stop6h 54m

Miami

Tue 11/4

8:30 am-12:28 pm

1 stop4h 58m

$258

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 10/26

6:00 am-1:11 pm

1 stop6h 11m

Miami

Tue 10/28

6:00 am-9:40 am

1 stop4h 40m

$258

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 12/9

10:49 am-5:25 pm

1 stop5h 36m

Miami

Sun 12/14

6:00 am-9:54 am

1 stop4h 54m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/25

Showing 1-10 of 37 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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida Keys (average of $328). Flying from Chicago Midway Airport to Florida Keys in March is currently the most expensive (average of $489). 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 September 25, 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
4,246 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
8,926 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
8,045 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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 $179. 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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida Keys (average of $328). Flying from Chicago Midway Airport to Florida Keys in March is currently the most expensive (average of $489). 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 September 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$262Average$543FlexibilityNo cancel feeOn-timeN/A

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