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$43+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$87
(Frontier)

One-way from

$43
(Cheapflightsfares)

Popular in

December

Cheapest in

May

Average price

$279

Good round-trip deal

$108 or less

Good one-way deal

$53 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 ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Trip.com deal was found by Cheapflights users on 2/20. 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.
Wed 3/123:14 pmMDW - TPA
Nonstop2h 41mFrontier
Wed 3/267:55 pmTPA - MDW
Nonstop2h 56mFrontier
Deal found 2/20$89
This eDestinos deal was found by Cheapflights users on 2/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/82:36 pmMDW - MIA
1 stop7h 39mFrontier
Tue 4/1510:36 amMIA - MDW
1 stop10h 09mFrontier
Deal found 2/20$99
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Tue 4/14:40 pmMDW - MCO
Nonstop2h 50mFrontier
Fri 4/45:54 pmMCO - MDW
Nonstop3h 01mFrontier
Deal found 2/19$118
This Frontier deal was found by Cheapflights users on 2/20. 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.
Fri 5/98:30 amMDW - FLL
1 stop12h 00mFrontier
Mon 5/1210:30 pmFLL - MDW
1 stop10h 49mFrontier
Deal found 2/20$140
This Frontier deal was found by Cheapflights users on 2/19. 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 4/68:00 amMDW - RSW
1 stop10h 51mFrontier
Tue 4/811:23 amRSW - MDW
1 stop9h 28mFrontier
Deal found 2/19$160
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 3/127:10 pmMDW - FLL
Nonstop2h 55mSouthwest
Wed 3/196:05 amFLL - MDW
Nonstop3h 15mSouthwest
Deal found 2/19$209
This Delta deal was found by Cheapflights users on 2/19. 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 4/16:00 amMDW - TPA
1 stop5h 28mDelta
Tue 4/156:00 amTPA - MDW
1 stop4h 07mDelta
Deal found 2/19$209
This Southwest deal was found by Cheapflights users on 2/19. 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 3/182:40 pmMDW - TPA
Nonstop2h 35mSouthwest
Tue 3/258:30 amTPA - MDW
Nonstop2h 45mSouthwest
Deal found 2/19$213
This Delta deal was found by Cheapflights users on 2/20. 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 4/112:51 pmMDW - FLL
1 stop5h 39mDelta
Wed 4/26:00 amFLL - MDW
1 stop7h 36mDelta
Deal found 2/20$217
This Delta deal was found by Cheapflights users on 2/20. 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 4/812:48 pmMDW - RSW
1 stop4h 58mDelta
Tue 4/156:00 pmRSW - MDW
1 stop5h 26mDelta
Deal found 2/20$217
This Delta deal was found by Cheapflights users on 2/20. 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 4/82:57 pmMDW - MIA
1 stop5h 21mDelta
Tue 4/158:05 amMIA - MDW
1 stop5h 30mDelta
Deal found 2/20$217
This Southwest deal was found by Cheapflights users on 2/20. 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.
Wed 3/1212:20 pmMDW - PNS
1 stop3h 45mSouthwest
Wed 4/1611:30 amPNS - MDW
1 stop5h 35mSouthwest
Deal found 2/20$217

Find flights from Midway to Florida within your budget

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 February 20, 2025.

Fly from

Midway

Fly to

Florida

Route

Depart

Return

Price

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 3/12

3:14 pm-6:55 pm

Nonstop2h 41m

Tampa

Wed 3/26

7:55 pm-9:51 pm

Nonstop2h 56m

$89

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 4/8

2:36 pm-11:15 pm

1 stop7h 39m

Miami

Tue 4/15

10:36 am-7:45 pm

1 stop10h 09m

$99

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 4/1

4:40 pm-8:30 pm

Nonstop2h 50m

Orlando

Fri 4/4

5:54 pm-7:55 pm

Nonstop3h 01m

$118

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Fri 5/9

8:30 am-9:30 pm

1 stop12h 00m

Fort Lauderdale

Mon 5/12

10:30 pm-8:19 am

1 stop10h 49m

$140

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sun 4/6

8:00 am-7:51 pm

1 stop10h 51m

Fort Myers SW Florida Intl

Thu 4/10

11:23 am-9:40 pm

1 stop11h 17m

$160

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Wed 3/12

7:10 pm-11:05 pm

Nonstop2h 55m

Fort Lauderdale

Wed 3/19

6:05 am-8:20 am

Nonstop3h 15m

$209

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 4/1

6:00 am-12:28 pm

1 stop5h 28m

Tampa

Tue 4/15

6:00 am-9:07 am

1 stop4h 07m

$209

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 3/18

2:40 pm-6:15 pm

Nonstop2h 35m

Tampa

Tue 3/25

8:30 am-10:15 am

Nonstop2h 45m

$213

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Tue 4/1

12:51 pm-7:30 pm

1 stop5h 39m

Fort Lauderdale

Wed 4/2

6:00 am-12:36 pm

1 stop7h 36m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 4/8

12:48 pm-6:46 pm

1 stop4h 58m

Fort Myers SW Florida Intl

Tue 4/15

6:00 pm-10:26 pm

1 stop5h 26m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from Midway to Florida

Get recent, data-driven insights about flights from Midway to Florida including ideal travel times, pricing trends, and more.

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 $231). 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 February 20, 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 February 20, 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
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

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
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

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
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

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
765 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

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
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

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 $43 on Frontier. Other airlines that offer cheap prices include Southwest from $90 and Delta from $105 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 cheapest flights from Chicago Midway Airport to Florida?

    On average you can expect to pay $159 for a flight from Chicago Midway Airport to Florida. The cheapest flight overall is $36 while the most popular route, (Chicago Midway - Fort Lauderdale) is currently priced at $156.

  • 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 $231). 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$53Average$203FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$69Average$207FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$95Average$320FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$178Average$419FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$400FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$270Average$423FlexibilityNo cancel feeOn-time71%
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