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$61+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$102
(Frontier)

One-way from

$61
(Cheapflightsfares)

Popular in

March

Cheapest in

August

Average price

$197

Good round-trip deal

$78 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 ($18 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 July 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 July 30, 2025.

This Frontier deal was found by Cheapflights users on 7/29. 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 9/199:48 amMDW - MCO
Nonstop2h 40mFrontier
Sun 9/217:25 amMCO - MDW
Nonstop2h 53mFrontier
Deal found 7/29$102
This Cheapflightsfares deal was found by Cheapflights users on 7/28. 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 9/126:21 amMDW - TPA
Nonstop2h 36mFrontier
Sun 9/1410:55 amTPA - MDW
Nonstop2h 49mFrontier
Deal found 7/28$122
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/109:30 amMDW - MIA
Nonstop3h 05mSouthwest
Wed 11/121:05 pmMIA - MDW
Nonstop3h 15mSouthwest
Deal found 7/28$137
This Frontier deal was found by Cheapflights users on 7/29. 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.
Thu 10/2310:03 pmMDW - MIA
Nonstop3h 00mFrontier
Mon 10/276:53 pmMIA - MDW
Nonstop3h 15mFrontier
Deal found 7/29$144
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:10 pmMDW - FLL
Nonstop2h 55mSouthwest
Wed 11/56:50 amFLL - MDW
Nonstop3h 05mSouthwest
Deal found 7/28$157
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/26:20 pmMDW - RSW
Nonstop2h 45mSouthwest
Wed 9/109:15 amRSW - MDW
Nonstop2h 50mSouthwest
Deal found 7/29$157
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:15 amMDW - TPA
Nonstop2h 30mSouthwest
Sat 11/17:05 amTPA - MDW
Nonstop2h 40mSouthwest
Deal found 7/27$157
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:15 amMDW - MCO
Nonstop2h 30mSouthwest
Wed 9/310:05 amMCO - MDW
Nonstop2h 45mSouthwest
Deal found 7/28$157
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1610:30 amMDW - JAX
Nonstop2h 15mSouthwest
Sat 9/202:05 pmJAX - MDW
Nonstop2h 25mSouthwest
Deal found 7/27$181
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
Tue 8/511:39 amMDW - FLL
1 stop6h 07mFrontier
Tue 8/126:00 amFLL - MDW
1 stop5h 40mFrontier
Deal found 7/29$186
This Delta deal was found by Cheapflights users on 7/28. 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.
Sat 9/610:31 amMDW - SRQ
1 stop4h 27mDelta
Tue 9/95:03 pmSRQ - MDW
1 stop5h 23mDelta
Deal found 7/28$197
This Delta deal was found by Cheapflights users on 7/27. 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 9/166:00 amMDW - JAX
1 stop4h 40mDelta
Sat 9/205:08 pmJAX - MDW
1 stop5h 02mDelta
Deal found 7/27$201

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 July 30, 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

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 9/19

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

Sun 9/21

7:25 am-9:18 am

Nonstop2h 53m

$102

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 9/12

6:21 am-9:57 am

Nonstop2h 36m

Tampa

Sun 9/14

10:55 am-12:44 pm

Nonstop2h 49m

$122

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 10/23

10:03 pm-2:03 am

Nonstop3h 00m

Miami

Mon 10/27

6:53 pm-9:08 pm

Nonstop3h 15m

$144

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 9/8

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

Wed 9/10

11:40 am-4:25 pm

1 stop5h 45m

$147

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Tue 8/26

8:25 am-12:25 pm

Nonstop3h 00m

Fort Lauderdale

Wed 9/3

7:00 am-9:10 am

Nonstop3h 10m

$157

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 9/2

6:20 pm-10:05 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Wed 9/10

9:15 am-11:05 am

Nonstop2h 50m

$157

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 10/25

5:45 pm-9:15 pm

Nonstop2h 30m

Tampa

Sat 11/1

7:05 am-8:45 am

Nonstop2h 40m

$157

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 8/27

6:15 am-9:45 am

Nonstop2h 30m

Orlando

Wed 9/3

10:05 am-11:50 am

Nonstop2h 45m

$157

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 9/16

10:30 am-1:45 pm

Nonstop2h 15m

Jacksonville

Sat 9/20

2:05 pm-3:30 pm

Nonstop2h 25m

$181

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Tue 8/5

11:39 am-6:46 pm

1 stop6h 07m

Fort Lauderdale

Tue 8/12

6:00 am-10:40 am

1 stop5h 40m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 58 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 July 30, 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 July 30, 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
4,241 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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.
Allegiant Air
7.2
Good
703 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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
5.9
Fair
3,237 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 $61 on Frontier. Other airlines that offer cheap prices include Southwest from $69 and Allegiant Air from $90 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 - Miami, Chicago Midway - Tampa or Chicago Midway - Orlando as they are the most popular.

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

    On average you can expect to pay $325 for a flight from Chicago Midway Airport to Florida. The cheapest flight overall is $68 while the most popular route, (Chicago Midway - Miami) is currently priced at $137.

  • 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 6 airlines flying from Midway to Florida

Discover the top 6 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$226FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$85Average$231FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$127Average$359FlexibilityNo cancel feeOn-time69%
DeltaCheapest$131Average$342FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$173Average$392FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$270Average$413FlexibilityNo cancel feeOn-time71%

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