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$50+ Cheap flights from Midway (MDW) to Florida

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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Midway to Florida

Keep the following information in mind while searching for Midway to Florida flight deals. Data was last updated September 11, 2025.

Round-trip from

$103
(Cheapflightsfares)

One-way from

$50
(Cheapflightsfares)

Popular in

March

Cheapest in

August

Average price

$190

Good round-trip deal

$90 or less

Good one-way deal

$64 or less
From Chicago Midway to Florida
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One-way flight from Chicago Midway to Florida
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Highest demand for flights based on searches. 7% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to Florida.
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Price to beat on a one-way flight from Chicago Midway to Florida.
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Find flight deals from Midway to Florida

Cheapest flights from Midway to Florida
Explore the most affordable flight options available from Midway to Florida. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/56:21 amMDW - TPA
Nonstop2h 36mFrontier
Sun 10/129:57 amTPA - MDW
Nonstop2h 47mFrontier
Deal found 9/10$103
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/275:28 pmMDW - MCO
Nonstop2h 42mFrontier
Fri 10/316:35 amMCO - MDW
Nonstop2h 57mFrontier
Deal found 9/11$103
This Frontier deal was found by Cheapflights users on 9/9. 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.
Mon 11/36:06 pmMDW - TPA
Nonstop2h 35mFrontier
Mon 11/1010:41 pmTPA - MDW
Nonstop2h 49mFrontier
Deal found 9/9$104
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/108:00 amMDW - MCO
Nonstop2h 41mFrontier
Thu 11/137:15 amMCO - MDW
Nonstop2h 57mFrontier
Deal found 9/10$104
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:21 amMDW - TPA
Nonstop2h 36mFrontier
Sun 10/129:57 amTPA - MDW
Nonstop2h 47mFrontier
Deal found 9/10$105
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:28 pmMDW - MCO
Nonstop2h 42mFrontier
Fri 10/242:26 pmMCO - MDW
Nonstop2h 54mFrontier
Deal found 9/10$105
This Frontier deal was found by Cheapflights users on 9/9. 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 11/77:50 amMDW - TPA
Nonstop2h 34mFrontier
Sun 11/910:41 pmTPA - MDW
Nonstop2h 49mFrontier
Deal found 9/9$106
This Frontier deal was found by Cheapflights users on 9/9. 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 10/175:28 pmMDW - MCO
Nonstop2h 42mFrontier
Thu 10/307:15 amMCO - MDW
Nonstop2h 57mFrontier
Deal found 9/9$106
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/317:50 amMDW - TPA
Nonstop2h 34mFrontier
Sun 11/210:41 pmTPA - MDW
Nonstop2h 49mFrontier
Deal found 9/9$107
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Fri 11/143:27 pmMDW - MCO
Nonstop2h 42mFrontier
Sat 11/158:30 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 9/11$107
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2511:31 amMDW - MCO
Nonstop2h 40mFrontier
Sun 11/27:15 amMCO - MDW
Nonstop2h 57mFrontier
Deal found 9/10$108
This Frontier deal was found by Cheapflights users on 9/9. 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.
Mon 10/139:00 amMDW - TPA
Nonstop2h 37mFrontier
Tue 10/147:30 amTPA - MDW
1 stop7h 08mFrontier
Deal found 9/9$109

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Florida 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 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Florida that are best for you.

Fly from

Midway

Fly to

Florida

Route

Depart

Return

Price

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sun 10/12

5:20 am-8:55 am

Nonstop2h 35m

Tampa

Sun 10/12

9:57 am-11:44 am

Nonstop2h 47m

$110

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 10/28

8:05 pm-11:35 pm

Nonstop2h 30m

Orlando

Tue 11/4

4:35 pm-6:25 pm

Nonstop2h 50m

$133

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 10/30

12:30 pm-5:44 am

1 stop16h 14m

Orlando

Sun 11/2

7:15 am-9:12 am

Nonstop2h 57m

$135

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Mon 10/27

6:55 pm-10:45 pm

Nonstop2h 50m

Fort Lauderdale

Wed 10/29

8:35 pm-10:45 pm

Nonstop3h 10m

$141

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Wed 10/8

5:35 am-1:00 pm

1 stop6h 25m

Fort Lauderdale

Sat 10/11

6:30 am-8:35 am

Nonstop3h 05m

$143

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 11/6

1:37 pm-12:34 am

1 stop9h 57m

Miami

Sun 11/9

6:00 am-11:30 am

1 stop30h 30m

$143

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 9/18

1:49 pm-10:42 pm

1 stop7h 53m

Miami

Mon 9/22

8:00 am-8:46 pm

1 stop13h 46m

$144

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 11/11

9:00 am-1:05 pm

Nonstop3h 05m

Miami

Fri 11/14

6:20 am-8:35 am

Nonstop3h 15m

$145

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 11/11

6:15 pm-10:00 pm

Nonstop2h 45m

Orlando

Thu 11/13

9:10 pm-11:00 pm

Nonstop2h 50m

$146

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Wed 11/12

6:30 pm-10:35 pm

Nonstop3h 05m

Fort Lauderdale

Sun 11/16

5:30 am-7:35 am

Nonstop3h 05m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 60 results
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Best time to book a flight from Midway to Florida

Have a flexible travel schedule? Discover the best time to fly to Florida 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

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

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida (average of $232). Flying from Chicago Midway Airport to Florida in March is currently the most expensive (average of $289). 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.

What is the cheapest time of day to fly from MDW to FL?

Find hourly flight availability from Midway to Florida. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Florida as you normally would.

Reviews of airlines servicing Florida

Get insights into the airlines that provide service to Florida. 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. Reviews last updated September 11, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Allegiant Air from Chicago Midway Airport to Florida. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

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
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

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.
Allegiant Air
7.2
Good
702 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

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
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

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
5.8
Fair
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

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. 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?

    For as low as $133, Frontier can have you in Florida from Chicago Midway Airport in 2h 30m. The distance between Chicago Midway Airport and Florida is about 990 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Florida one-way?

    One-way options have recently been found by users for as low as $54 on Frontier. Other airlines that offer cheap prices include Southwest from $67 and Delta from $99 one-way.

  • What are the most popular routes from Chicago Midway Airport to Florida?

    When deciding which route to take from Chicago Midway Airport to Florida consider Chicago Midway - Orlando, Chicago Midway - Miami or Chicago Midway - Tampa as they are the most popular.

  • What are the cheapest flights from Chicago Midway Airport to Florida?

    On average you can expect to pay $228 for a flight from Chicago Midway Airport to Florida. The cheapest flight overall is $48 while the most popular route, (Chicago Midway - Orlando) is currently priced at $103.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Florida 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?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida (average of $232). Flying from Chicago Midway Airport to Florida in March is currently the most expensive (average of $289). 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

See prices for flight routes from nearby airports that may be better suited for you.
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O'Hare Intl to Burbank flights

Top 5 airlines flying from Midway to Florida

Discover the top 5 airlines that operate flights from Midway to Florida. 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 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$228FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$234FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$127Average$321FlexibilityNo cancel feeOn-time69%
DeltaCheapest$131Average$351FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$174Average$392FlexibilityNo cancel feeOn-time63%

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