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Florida Keys

$45+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — EYW
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
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 January 12, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$93
(Frontier)

One-way from

$45
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$220
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. 8% potential increase in price ($23 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 January 2026
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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 January 12, 2026.

This Frontier deal was found by Cheapflights users on 1/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/116:15 am
MDW
-
MIA
1 stop10h 34m
Frontier
Thu 2/1911:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/12$93
This CheapOair deal was found by Cheapflights users on 1/12. 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.
Sun 2/226:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Tue 2/2412:25 pm
MIA
-
MDW
1 stop7h 42m
Frontier
Deal found 1/12$94
This Super.com deal was found by Cheapflights users on 1/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Fri 3/611:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/12$98
This Frontier deal was found by Cheapflights users on 1/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Thu 3/511:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/12$99
This Frontier deal was found by Cheapflights users on 1/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Sat 3/711:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/12$103
This Super.com deal was found by Cheapflights users on 1/10. 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 2/156:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Thu 2/195:05 am
MIA
-
MDW
1 stop7h 22m
Frontier
Deal found 1/10$104
This CheapOair deal was found by Cheapflights users on 1/11. 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.
Mon 2/99:45 am
MDW
-
MIA
1 stop8h 41m
Frontier
Thu 2/1211:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/11$105
This Kiwi.com deal was found by Cheapflights users on 1/10. 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 2/116:15 am
MDW
-
MIA
1 stop10h 34m
Frontier
Thu 2/1211:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/10$106
This Super.com deal was found by Cheapflights users on 1/10. 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 2/226:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Thu 2/2611:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/10$107
This Super.com deal was found by Cheapflights users on 1/10. 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.
Mon 3/166:00 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Thu 3/1911:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/10$108
This Super.com deal was found by Cheapflights users on 1/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Mon 3/911:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/12$109
This Delta deal was found by Cheapflights users on 1/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:45 pm
MDW
-
EYW
1 stop5h 57m
Delta
Wed 3/45:56 pm
EYW
-
MDW
1 stop5h 35m
Delta
Deal found 1/12$289

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 January 12, 2026.
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 2/10

5:30 pm-9:30 pm

Nonstop3h 00m

Miami

Sat 2/14

12:15 pm-7:30 pm

1 stop8h 15m

$191

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 2/23

9:40 am-1:45 pm

Nonstop3h 05m

Miami

Fri 2/27

6:10 am-12:55 pm

1 stop7h 45m

$207

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 2/9

9:40 am-1:45 pm

Nonstop3h 05m

Miami

Wed 2/11

2:00 pm-9:50 pm

1 stop8h 50m

$207

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 2/10

12:46 pm-6:30 pm

1 stop4h 44m

Miami

Thu 2/12

8:15 am-11:59 am

1 stop4h 44m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 2/21

4:13 pm-10:47 pm

1 stop5h 34m

Miami

Tue 2/24

8:15 am-11:59 am

1 stop4h 44m

$217

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 3/5

6:00 am-12:23 pm

1 stop5h 23m

Miami

Sat 3/14

6:00 am-9:56 am

1 stop4h 56m

$237

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 3/9

6:35 am-2:35 pm

1 stop7h 00m

Miami

Wed 3/11

6:30 am-8:45 am

Nonstop3h 15m

$247

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 1/24

10:46 am-5:17 pm

1 stop5h 31m

Miami

Sat 1/31

5:50 am-9:53 am

1 stop5h 03m

$247

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 1/31

12:45 pm-9:35 pm

2 stops7h 50m

Miami

Sat 2/7

6:30 am-8:40 am

Nonstop3h 10m

$251

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 2/1

9:40 am-1:45 pm

Nonstop3h 05m

Miami

Sat 2/7

6:30 am-8:40 am

Nonstop3h 10m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/10

Showing 1-10 of 40 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida Keys (average of $287). 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 January 12, 2026.
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
4,255 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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
4,255 reviews
Southwest
8.0
Very good
4,255 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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
8,036 reviews
Southwest
8.0
Very good
4,255 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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
9,144 reviews
Southwest
8.0
Very good
4,255 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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
8,297 reviews
Southwest
8.0
Very good
4,255 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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
5.7
Fair
3,055 reviews
Southwest
8.0
Very good
4,255 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

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 $191. 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida Keys (average of $287). 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 January 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$262Average$526FlexibilityNo cancel feeOn-timeN/A

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