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$52+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
Mar 30 — Apr 61
Sun 3/30
Sun 4/6
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 March 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$106
(Frontier)

One-way from

$52
(Frontier)

Popular in

December

Cheapest in

May

Average price

$338

Good round-trip deal

$122 or less

Good one-way deal

$49 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. 11% potential increase in price ($34 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 March 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 March 25, 2025.

This Frontier deal was found by Cheapflights users on 3/24. 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 4/141:23 pmMDW - MCO
Nonstop2h 54mFrontier
Wed 4/165:34 pmMCO - MDW
Nonstop3h 01mFrontier
Deal found 3/24$106
This Frontier deal was found by Cheapflights users on 3/24. 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 4/124:10 pmMDW - TPA
Nonstop2h 40mFrontier
Wed 4/167:41 pmTPA - MDW
Nonstop2h 52mFrontier
Deal found 3/24$131
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Thu 4/108:00 amMDW - MIA
Nonstop3h 08mFrontier
Sat 4/1212:25 pmMIA - MDW
Nonstop3h 35mFrontier
Deal found 3/24$147
This Southwest deal was found by Cheapflights users on 3/24. 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 5/102:25 pmMDW - FLL
Nonstop3h 00mSouthwest
Sat 5/176:25 amFLL - MDW
Nonstop3h 10mSouthwest
Deal found 3/24$177
This Southwest deal was found by Cheapflights users on 3/24. 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.
Sun 5/48:40 pmMDW - MIA
Nonstop3h 00mSouthwest
Wed 5/77:00 amMIA - MDW
Nonstop3h 10mSouthwest
Deal found 3/24$177
This Southwest deal was found by Cheapflights users on 3/23. 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 4/227:55 pmMDW - MCO
Nonstop2h 35mSouthwest
Tue 4/292:00 pmMCO - MDW
1 stop4h 35mSouthwest
Deal found 3/23$189
This Delta deal was found by Cheapflights users on 3/23. 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 5/176:00 amMDW - TPA
1 stop5h 30mDelta
Wed 5/218:30 amTPA - MDW
1 stop4h 23mDelta
Deal found 3/23$197
This Delta deal was found by Cheapflights users on 3/24. 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 5/1310:25 amMDW - MCO
1 stop7h 07mDelta
Sat 5/175:45 pmMCO - MDW
1 stop4h 29mDelta
Deal found 3/24$197
This Southwest deal was found by Cheapflights users on 3/24. 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 4/226:20 amMDW - PBI
1 stop7h 50mSouthwest
Tue 4/296:40 pmPBI - MDW
1 stop5h 30mSouthwest
Deal found 3/24$199
This Southwest deal was found by Cheapflights users on 3/24. 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 5/36:30 pmMDW - TPA
Nonstop2h 30mSouthwest
Tue 5/62:50 pmTPA - MDW
1 stop7h 15mSouthwest
Deal found 3/24$203
This Delta deal was found by Cheapflights users on 3/24. 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 5/1310:25 amMDW - FLL
1 stop7h 11mDelta
Sat 5/176:00 amFLL - MDW
1 stop7h 28mDelta
Deal found 3/24$217
This Delta deal was found by Cheapflights users on 3/24. 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 4/264:00 pmMDW - RSW
1 stop6h 03mDelta
Sat 5/36:00 pmRSW - MDW
1 stop5h 22mDelta
Deal found 3/24$217

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 March 25, 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

Mon 4/14

1:23 pm-5:17 pm

Nonstop2h 54m

Orlando

Wed 4/16

5:34 pm-7:35 pm

Nonstop3h 01m

$106

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 4/12

4:10 pm-7:50 pm

Nonstop2h 40m

Tampa

Wed 4/16

7:41 pm-9:33 pm

Nonstop2h 52m

$131

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 4/10

8:00 am-12:08 pm

Nonstop3h 08m

Miami

Sat 4/12

12:25 pm-3:00 pm

Nonstop3h 35m

$147

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Sat 5/10

2:25 pm-6:25 pm

Nonstop3h 00m

Fort Lauderdale

Sat 5/17

6:25 am-8:35 am

Nonstop3h 10m

$177

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 5/4

8:40 pm-12:40 am

Nonstop3h 00m

Miami

Wed 5/7

7:00 am-9:10 am

Nonstop3h 10m

$177

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 5/3

6:40 pm-10:15 pm

Nonstop2h 35m

Orlando

Sat 5/10

6:25 am-8:15 am

Nonstop2h 50m

$177

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 5/17

9:20 am-4:18 pm

1 stop5h 58m

Tampa

Wed 5/21

8:30 am-11:53 am

1 stop4h 23m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 5/13

10:25 am-6:32 pm

1 stop7h 07m

Orlando

Sat 5/17

5:45 pm-9:14 pm

1 stop4h 29m

$197

ChicagoWest Palm Beach

MDW - PBI

MDWPBI

Chicago Midway

Tue 4/22

6:20 am-3:10 pm

1 stop7h 50m

Palm Beach Intl

Tue 4/29

6:40 pm-11:10 pm

1 stop5h 30m

$199

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 5/3

6:30 pm-10:00 pm

Nonstop2h 30m

Tampa

Tue 5/6

2:50 pm-9:05 pm

1 stop7h 15m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

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 $229). 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 March 25, 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.

Rainfall in Florida by month

Plan your trip to Florida by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Florida ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Florida when rainfall is around 2.4 in.

Temperature in Florida by month

Plan your trip to Florida by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Florida, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 March 25, 2025.
See what other customers who have flown with Southwest, Delta and Avelo Airlines from Chicago to Florida have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

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
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

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
8.0
Very good
7,890 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

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.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

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
7.3
Good
730 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

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
6.0
Okay
3,273 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

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.

  • 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 $88 and Allegiant Air from $93 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 - Orlando 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 $196 for a flight from Chicago Midway Airport to Florida. The cheapest flight overall is $39 while the most popular route, (Chicago Midway - Miami) is currently priced at $177.

  • 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 $229). 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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Midway to Los Angeles 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 March 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$201FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$84Average$214FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$95Average$334FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$179Average$412FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$410FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$260Average$440FlexibilityNo cancel feeOn-time71%
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