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$59+ 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 6/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Cheapflightsfares)

One-way from

$59
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$197

Good round-trip deal

$94 or less

Good one-way deal

$62 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 April 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 April 30, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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.
Mon 7/149:12 pmMDW - MCO
Nonstop2h 51mFrontier
Fri 7/186:23 pmMCO - MDW
Nonstop2h 59mFrontier
Deal found 4/28$117
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Thu 5/224:11 pmMDW - TPA
Nonstop2h 43mFrontier
Sun 5/258:49 pmTPA - MDW
Nonstop2h 52mFrontier
Deal found 4/29$132
This Southwest deal was found by Cheapflights users on 4/29. 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.
Mon 7/146:50 pmMDW - TPA
Nonstop2h 35mSouthwest
Fri 7/188:05 pmTPA - MDW
Nonstop2h 45mSouthwest
Deal found 4/29$159
This Southwest deal was found by Cheapflights users on 4/28. 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.
Sun 6/18:45 pmMDW - FLL
Nonstop2h 55mSouthwest
Wed 6/47:45 amFLL - MDW
Nonstop3h 10mSouthwest
Deal found 4/28$171
This Southwest deal was found by Cheapflights users on 4/28. 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.
Thu 6/125:15 amMDW - PNS
1 stop3h 40mSouthwest
Tue 6/179:35 amPNS - MDW
Nonstop2h 15mSouthwest
Deal found 4/28$187
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/138:36 pmMDW - FLL
1 stop25h 55mAllegiant Air
Sun 6/158:39 pmFLL - MDW
1 stop24h 07mAllegiant Air
Deal found 4/29$192
This Southwest deal was found by Cheapflights users on 4/28. 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.
Sun 6/18:40 pmMDW - MIA
Nonstop3h 00mSouthwest
Wed 6/47:00 amMIA - MDW
Nonstop3h 10mSouthwest
Deal found 4/28$197
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/26:00 amMDW - TPA
1 stop7h 14mDelta
Fri 6/65:53 pmTPA - MDW
1 stop4h 34mDelta
Deal found 4/29$197
This Southwest deal was found by Cheapflights users on 4/28. 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.
Tue 7/87:00 pmMDW - MCO
Nonstop2h 45mSouthwest
Sat 7/126:40 amMCO - MDW
Nonstop2h 45mSouthwest
Deal found 4/28$197
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/245:55 pmMDW - MCO
1 stop4h 59mDelta
Sun 5/256:15 amMCO - MDW
1 stop6h 38mDelta
Deal found 4/29$200
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/229:50 amMDW - FLL
1 stop11h 13mFrontier
Sat 5/2410:50 pmFLL - MDW
1 stop11h 10mFrontier
Deal found 4/28$208
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/128:03 pmMDW - MIA
1 stop8h 19mFrontier
Mon 5/1910:42 pmMIA - MDW
1 stop11h 38mFrontier
Deal found 4/28$210

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 April 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

Mon 7/14

9:12 pm-1:03 am

Nonstop2h 51m

Orlando

Fri 7/18

6:23 pm-8:22 pm

Nonstop2h 59m

$117

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 5/22

4:11 pm-7:54 pm

Nonstop2h 43m

Tampa

Sun 5/25

8:49 pm-10:41 pm

Nonstop2h 52m

$132

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Mon 7/14

6:50 pm-10:25 pm

Nonstop2h 35m

Tampa

Fri 7/18

8:05 pm-9:50 pm

Nonstop2h 45m

$159

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Sun 6/1

8:45 pm-12:40 am

Nonstop2h 55m

Fort Lauderdale

Wed 6/4

7:45 am-9:55 am

Nonstop3h 10m

$171

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 6/12

5:15 am-8:55 am

1 stop3h 40m

Pensacola

Tue 6/17

9:35 am-11:50 am

Nonstop2h 15m

$187

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Fri 6/13

8:36 pm-11:31 pm

1 stop25h 55m

Fort Lauderdale

Sun 6/15

8:39 pm-7:46 pm

1 stop24h 07m

$192

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Mon 6/2

6:00 am-2:14 pm

1 stop7h 14m

Tampa

Fri 6/6

5:53 pm-9:27 pm

1 stop4h 34m

$197

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 6/1

8:40 pm-12:40 am

Nonstop3h 00m

Miami

Wed 6/4

7:00 am-9:10 am

Nonstop3h 10m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 7/8

7:00 pm-10:45 pm

Nonstop2h 45m

Orlando

Sat 7/12

6:40 am-8:25 am

Nonstop2h 45m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 5/24

5:55 pm-11:54 pm

1 stop4h 59m

Orlando

Sun 5/25

6:15 am-9:40 am

1 stop4h 25m

$200

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 April 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.

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 April 30, 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
4,295 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Food

7.1

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
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Food

7.1

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
7,929 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Food

7.1

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
734 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Food

7.1

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
3,284 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.2

Food

7.1

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 $59 on Frontier. Other airlines that offer cheap prices include Southwest from $80 and Allegiant Air from $96 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 $222 for a flight from Chicago Midway Airport to Florida. The cheapest flight overall is $82 while the most popular route, (Chicago Midway - Orlando) is currently priced at $120.

  • 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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$215FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$84Average$209FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$95Average$332FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$180Average$405FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$385FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$270Average$423FlexibilityNo cancel feeOn-time71%

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