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$79+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$126
(Cheapflightsfares)

One-way from

$79
(Southwest)

Popular in

March

Cheapest in

September

Average price

$289

Good round-trip deal

$86 or less

Good one-way deal

$54 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. 6% potential increase in price ($16 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 June 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 junio 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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.
jue. 10/98:39 amMDW - MCO
Nonstop2h 41mFrontier
lun. 10/135:50 amMCO - MDW
Nonstop2h 54mFrontier
Deal found 6/12$126
This Priceline deal was found by Cheapflights users on 6/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/156:21 amMDW - TPA
Nonstop2h 39mFrontier
lun. 9/2210:55 amTPA - MDW
Nonstop2h 49mFrontier
Deal found 6/11$128
This CheapOair deal was found by Cheapflights users on 6/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/106:15 amMDW - FLL
1 stop10h 43mFrontier
lun. 10/136:55 pmFLL - MDW
1 stop5h 30mFrontier
Deal found 6/10$145
This CheapOair deal was found by Cheapflights users on 6/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/1112:48 pmMDW - MIA
1 stop9h 10mFrontier
lun. 9/156:42 pmMIA - MDW
1 stop5h 43mFrontier
Deal found 6/10$145
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/166:00 pmMDW - FLL
Nonstop3h 00mSouthwest
sáb. 9/206:45 amFLL - MDW
Nonstop3h 00mSouthwest
Deal found 6/11$157
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/87:50 amMDW - RSW
Nonstop2h 40mSouthwest
mié. 10/154:20 pmRSW - MDW
Nonstop2h 50mSouthwest
Deal found 6/11$157
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/222:10 pmMDW - MIA
Nonstop3h 00mSouthwest
sáb. 9/274:05 pmMIA - MDW
Nonstop3h 10mSouthwest
Deal found 6/10$157
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/78:05 pmMDW - TPA
Nonstop2h 35mSouthwest
lun. 8/116:55 amTPA - MDW
Nonstop2h 40mSouthwest
Deal found 6/10$157
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/67:55 pmMDW - MCO
Nonstop2h 35mSouthwest
mié. 8/137:10 amMCO - MDW
Nonstop2h 45mSouthwest
Deal found 6/10$158
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/39:55 amMDW - JAX
2 stops7h 05mSouthwest
mar. 9/97:20 amJAX - MDW
2 stops8h 20mSouthwest
Deal found 6/11$187
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/124:22 pmMDW - TPA
1 stop5h 57mDelta
mar. 7/227:50 amTPA - MDW
1 stop5h 08mDelta
Deal found 6/11$197
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/29:30 amMDW - JAX
1 stop7h 06mDelta
mié. 12/106:30 amJAX - MDW
1 stop6h 25mDelta
Deal found 6/10$197

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 junio 12, 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

jue. 10/9

8:39 am-12:20 pm

Nonstop2h 41m

Orlando

lun. 10/13

5:50 am-7:44 am

Nonstop2h 54m

$126

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

jue. 9/11

12:48 pm-10:58 pm

1 stop9h 10m

Miami

lun. 9/15

6:42 pm-11:25 pm

1 stop5h 43m

$145

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

mar. 8/12

11:39 am-11:05 pm

1 stop10h 26m

Tampa

jue. 8/14

8:32 pm-10:24 pm

Nonstop2h 52m

$151

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

mié. 9/3

6:00 pm-10:00 pm

Nonstop3h 00m

Fort Lauderdale

mié. 9/10

7:00 am-9:10 am

Nonstop3h 10m

$157

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

lun. 9/22

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

sáb. 9/27

4:05 pm-6:15 pm

Nonstop3h 10m

$157

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

jue. 8/7

8:05 pm-11:40 pm

Nonstop2h 35m

Tampa

lun. 8/11

6:55 am-8:35 am

Nonstop2h 40m

$157

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

dom. 8/24

6:55 pm-10:40 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

sáb. 8/30

4:25 pm-6:15 pm

Nonstop2h 50m

$158

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

mié. 8/6

7:55 pm-11:30 pm

Nonstop2h 35m

Orlando

mié. 8/13

7:10 am-8:55 am

Nonstop2h 45m

$158

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

mié. 9/3

9:55 am-6:00 pm

2 stops7h 05m

Jacksonville

mar. 9/9

7:20 am-2:40 pm

2 stops8h 20m

$187

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

mar. 8/5

11:39 am-6:46 pm

1 stop6h 07m

Fort Lauderdale

mar. 8/12

6:00 am-10:40 am

1 stop5h 40m

$190

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 $228). 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 junio 12, 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 junio 12, 2025.
See what other customers who have flown with Southwest, Delta and Allegiant Air 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
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

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
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

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
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

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 $79 on Southwest. Other airlines that offer cheap prices include Frontier from $85 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 - 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 $223 for a flight from Chicago Midway Airport to Florida. The cheapest flight overall is $88 while the most popular route, (Chicago Midway - Orlando) is currently priced at $126.

  • 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 $228). 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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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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$208FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$85Average$226FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$95Average$367FlexibilityNo cancel feeOn-time69%
DeltaCheapest$131Average$360FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$181Average$397FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$270Average$423FlexibilityNo cancel feeOn-time71%

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