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$48+ 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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 October 28, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$101
(Kiwi.com)

One-way from

$48
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$227

Good round-trip deal

$139 or less

Good one-way deal

$70 or less
Provider with most accurate pricing for Chicago (CHI)-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Orlando (ORL) flights.
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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. 6% potential increase in price ($17 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 October 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 October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Mon 12/153:10 pmMDW - MCO
Nonstop2h 48mFrontier
Fri 12/197:58 pmMCO - MDW
Nonstop3h 00mFrontier
Deal found 10/26$101
This Frontier deal was found by Cheapflights users on 10/27. 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.
Mon 11/104:09 pmMDW - MCO
1 stop7h 50mFrontier
Sat 11/158:30 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 10/27$103
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/910:12 amMDW - MCO
Nonstop2h 38mFrontier
Thu 11/137:15 amMCO - MDW
Nonstop2h 57mFrontier
Deal found 10/28$104
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Sat 12/62:59 pmMDW - MIA
Nonstop3h 10mFrontier
Sat 12/139:38 amMIA - MDW
1 stop12h 44mFrontier
Deal found 10/26$105
This Booking.com deal was found by Cheapflights users on 10/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/111:56 pmMDW - MCO
1 stop24h 11mFrontier
Thu 11/137:15 amMCO - MDW
Nonstop2h 57mFrontier
Deal found 10/27$105
This Frontier deal was found by Cheapflights users on 10/26. 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 11/206:05 amMDW - MIA
1 stop10h 04mFrontier
Wed 11/262:44 pmMIA - MDW
Nonstop3h 13mFrontier
Deal found 10/26$106
This Frontier deal was found by Cheapflights users on 10/26. 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 11/136:30 amMDW - TPA
1 stop10h 07mFrontier
Sun 11/1610:41 pmTPA - MDW
Nonstop2h 49mFrontier
Deal found 10/26$106
This CheapOair deal was found by Cheapflights users on 10/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/205:30 pmMDW - MCO
Nonstop2h 48mFrontier
Sun 11/232:34 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 10/26$107
This WAYA deal was found by Cheapflights users on 10/28. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:16 pmMDW - MIA
Nonstop3h 10mFrontier
Wed 12/245:30 amMIA - MDW
1 stop8h 51mFrontier
Deal found 10/28$108
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:12 amMDW - TPA
1 stop17h 14mFrontier
Wed 12/315:45 amTPA - MDW
1 stop17h 27mFrontier
Deal found 10/28$108
This Trip.com deal was found by Cheapflights users on 10/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:37 pmMDW - MCO
Nonstop2h 46mFrontier
Fri 12/128:40 pmMCO - MDW
Nonstop2h 59mFrontier
Deal found 10/26$108
This CheapOair deal was found by Cheapflights users on 10/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/82:05 pmMDW - MIA
Nonstop3h 00mFrontier
Sat 11/152:20 pmMIA - MDW
1 stop21h 06mFrontier
Deal found 10/26$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 October 28, 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

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Sun 1/25

6:10 am-10:15 am

Nonstop3h 05m

Fort Lauderdale

Sun 2/1

5:45 am-8:00 am

Nonstop3h 15m

$167

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 1/13

6:00 am-1:35 pm

1 stop6h 35m

Miami

Tue 1/13

2:35 pm-4:50 pm

Nonstop3h 15m

$167

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Sun 11/16

7:15 pm-11:15 pm

Nonstop3h 00m

Fort Lauderdale

Tue 11/18

7:35 am-11:25 am

1 stop4h 50m

$168

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 11/9

5:40 am-12:47 pm

1 stop6h 07m

Orlando

Sun 11/16

7:15 am-9:12 am

Nonstop2h 57m

$176

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 11/19

7:10 am-10:45 am

Nonstop2h 35m

Tampa

Wed 11/19

4:30 pm-6:15 pm

Nonstop2h 45m

$179

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 12/6

1:15 pm-8:45 pm

1 stop6h 30m

Miami

Wed 12/10

1:05 pm-3:20 pm

Nonstop3h 15m

$187

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Fri 1/30

1:15 pm-9:00 pm

1 stop6h 45m

Fort Myers SW Florida Intl

Mon 2/2

11:35 am-4:25 pm

1 stop5h 50m

$189

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Thu 1/29

10:00 am-4:10 pm

1 stop5h 10m

Fort Myers SW Florida Intl

Mon 2/2

6:50 am-1:55 pm

2 stops8h 05m

$194

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 12/2

5:13 pm-10:54 pm

1 stop4h 41m

Tampa

Mon 12/8

7:06 pm-11:47 pm

1 stop5h 41m

$197

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 1/17

6:45 am-2:49 pm

1 stop7h 04m

Tampa

Sun 1/18

11:45 am-5:34 pm

1 stop6h 49m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida (average of $56). 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 October 28, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 7% on flights from Chicago Midway Airport to Florida by exploring options for tickets at noon.

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 October 26, 2025.

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. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 28, 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
4,237 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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
7,993 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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
695 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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
8,111 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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
3,122 reviews
Southwest
8.0
Very good
4,237 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

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 $167, Southwest can have you in Florida from Chicago Midway Airport in 3h 05m. The distance between Chicago Midway Airport and Florida is about 1168 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 $52 on Frontier. Other airlines that offer cheap prices include Southwest from $66 and Delta from $115 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 - Fort Lauderdale as they are the most popular.

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

    On average you can expect to pay $236 for a flight from Chicago Midway Airport to Florida. The cheapest flight overall is $29 while the most popular route, (Chicago Midway - Orlando) is currently priced at $54.

  • 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Florida (average of $56). 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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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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$232FlexibilityNo cancel feeOn-time65%
FrontierCheapest$69Average$225FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$127Average$352FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$173Average$389FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$348FlexibilityNo cancel feeOn-timeN/A

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