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$44+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap 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 January 27, 2026.

This Frontier deal was found by Cheapflights users on 1/27. 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 Frontier 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 2/1911:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/27$85
This Frontier deal was found by Cheapflights users on 1/26. 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.
Sat 3/76:00 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Sat 3/1411:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/26$89
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:00 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Sat 3/1411:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/25$90
This Frontier deal was found by Cheapflights users on 1/26. 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 3/56:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Sat 3/1411:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/26$91
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 3/86:00 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Sat 3/1411:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/26$92
This Frontier deal was found by Cheapflights users on 1/25. 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 Frontier 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
Tue 2/2412:25 pm
MIA
-
MDW
1 stop7h 42m
Frontier
Deal found 1/25$97
This Priceline deal was found by Cheapflights users on 1/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:00 am
MDW
-
MIA
1 stop9h 49m
Frontier
Wed 3/253:25 pm
MIA
-
MDW
Nonstop3h 23m
Frontier
Deal found 1/25$98
This Frontier deal was found by Cheapflights users on 1/26. 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.
Sat 3/76:00 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Mon 3/1611:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/26$99
This Frontier deal was found by Cheapflights users on 1/26. 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 2/226:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Wed 2/2512:10 pm
MIA
-
MDW
1 stop7h 57m
Frontier
Deal found 1/26$100
This Frontier deal was found by Cheapflights users on 1/26. 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 3/56:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Mon 3/1611:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Deal found 1/26$101
This Trip.com deal was found by Cheapflights users on 1/25. 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.
Mon 2/91:00 pm
MDW
-
MCO
Nonstop2h 49m
Frontier
Fri 2/1312:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Deal found 1/25$101
This Frontier deal was found by Cheapflights users on 1/26. 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.
Sat 3/72:56 pm
MDW
-
MCO
Nonstop2h 46m
Frontier
Wed 3/114:05 pm
MCO
-
MDW
Nonstop3h 08m
Frontier
Deal found 1/26$102

Find flight deals from Midway to Florida

Keep the following information in mind while searching for Midway to Florida flight deals. Data was last updated January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$85
(Frontier)

One-way from

$44
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$211

Good round-trip deal

$139 or less

Good one-way deal

$67 or less
Provider with most accurate pricing for Chicago (CHI)-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Orlando (ORL) flights.
Search Deals
From Chicago Midway to Florida
Search Deals
One-way flight from Chicago Midway to Florida
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($5 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 January 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Florida.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Florida.
Search Deals

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 January 27, 2026.
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

Tue 2/24

3:15 pm-6:50 pm

Nonstop2h 35m

Orlando

Wed 2/25

7:25 am-9:20 am

Nonstop2h 55m

$157

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 2/24

7:00 am-10:45 am

Nonstop2h 45m

Orlando

Wed 3/4

7:25 am-9:20 am

Nonstop2h 55m

$157

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 2/21

4:05 pm-7:40 pm

Nonstop2h 35m

Orlando

Wed 2/25

7:25 am-9:20 am

Nonstop2h 55m

$177

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 2/21

6:50 pm-10:30 pm

Nonstop2h 40m

Orlando

Tue 2/24

7:25 am-9:20 am

Nonstop2h 55m

$177

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 2/22

4:25 pm-8:00 pm

Nonstop2h 35m

Orlando

Wed 2/25

7:25 am-9:20 am

Nonstop2h 55m

$178

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sun 2/22

7:50 am-3:15 pm

1 stop6h 25m

Tampa

Wed 2/25

7:15 am-9:05 am

Nonstop2h 50m

$188

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 2/24

11:30 am-3:05 pm

Nonstop2h 35m

Orlando

Tue 3/3

7:05 pm-9:00 pm

Nonstop2h 55m

$188

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 3/1

7:20 pm-11:00 pm

Nonstop2h 40m

Orlando

Sun 3/8

10:55 pm-12:50 am

Nonstop2h 55m

$188

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sun 2/22

8:35 pm-12:20 am

Nonstop2h 45m

Fort Myers SW Florida Intl

Thu 2/26

6:35 am-8:35 am

Nonstop3h 00m

$189

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 3/7

4:13 pm-12:03 am

1 stop6h 50m

Orlando

Wed 3/11

11:30 am-5:22 pm

1 stop6h 52m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida (average of $49). Flying from Chicago Midway Airport to Florida in June is currently the most expensive (average of $125). 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 January 27, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 9% on flights from Chicago Midway Airport to Florida by exploring options for tickets in the afternoon.

What is the cheapest day to fly from Chicago Midway Airport to Florida?

Use this chart to determine the cheapest time to fly round-trip from Midway to Florida. Price data was last updated on January 24, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Florida flight should consider departing on Wednesday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Chicago Midway Airport to Florida?

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 January 27, 2026.
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
4,268 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

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
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

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
7.9
Good
8,119 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

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
706 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

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
8,384 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

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
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

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 $157, Southwest can have you in Florida from Chicago Midway Airport in 2h 35m. 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 $30 on Frontier. Other airlines that offer cheap prices include Allegiant Air from $55 and Southwest from $78 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 - Fort Lauderdale, Chicago Midway - Miami or Chicago Midway - Orlando as they are the most popular.

  • What are the most reliable airlines from Chicago Midway Airport to Florida?

    Before booking your flight to Florida from Chicago Midway Airport, check out the most reliable airlines to get you to your destination on time: Southwest (66%), Frontier (50%), Volaris( 50%).

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

    On average you can expect to pay $205 for a flight from Chicago Midway Airport to Florida. The cheapest flight overall is $39 while the most popular route, (Chicago Midway - Fort Lauderdale) is currently priced at $128.

  • 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida (average of $49). Flying from Chicago Midway Airport to Florida in June is currently the most expensive (average of $125). 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 Jacksonville flights
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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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$35Average$161FlexibilityNo cancel feeOn-time65%
FrontierCheapest$39Average$187FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$411FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$119Average$395FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$171Average$380FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$203Average$357FlexibilityNo cancel feeOn-time71%

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