HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Florida

$60+ 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
avr. 20 — avr. 271
dim. 4/20
dim. 4/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Florida with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 avril 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$100
(Frontier)

One-way from

$60
(CheapOair)

Popular in

March

Cheapest in

September

Average price

$193

Good round-trip deal

$102 or less

Good one-way deal

$59 or less
Provider with most accurate pricing for Chicago (CHI)-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Orlando (ORL) flights.
Search Deals
From Chicago Midway to Florida
Search Deals
One-way flight from Chicago Midway to Florida
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Florida.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Florida.
Search Deals

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 avril 15, 2025.

This Frontier deal was found by Cheapflights users on 4/14. 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.
dim. 5/44:00 pmMDW - TPA
Nonstop2h 43mFrontier
jeu. 5/88:48 pmTPA - MDW
Nonstop2h 52mFrontier
Deal found 4/14$100
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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.
ven. 5/91:19 pmMDW - MCO
Nonstop2h 44mFrontier
dim. 5/113:33 pmMCO - MDW
Nonstop2h 57mFrontier
Deal found 4/14$125
This Southwest deal was found by Cheapflights users on 4/14. 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. 5/276:55 amMDW - TPA
Nonstop2h 30mSouthwest
mar. 6/37:25 amTPA - MDW
Nonstop2h 45mSouthwest
Deal found 4/14$159
This Southwest deal was found by Cheapflights users on 4/14. 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. 6/248:45 pmMDW - FLL
Nonstop3h 00mSouthwest
mer. 6/256:50 amFLL - MDW
Nonstop3h 05mSouthwest
Deal found 4/14$171
This Southwest deal was found by Cheapflights users on 4/14. 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.
mer. 5/145:10 pmMDW - MIA
Nonstop2h 55mSouthwest
mer. 5/217:00 amMIA - MDW
Nonstop3h 10mSouthwest
Deal found 4/14$177
This Southwest deal was found by Cheapflights users on 4/14. 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.
mer. 5/147:10 amMDW - MCO
Nonstop2h 30mSouthwest
mer. 5/216:25 pmMCO - MDW
Nonstop2h 50mSouthwest
Deal found 4/14$177
This Southwest deal was found by Cheapflights users on 4/13. 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.
mer. 6/44:55 pmMDW - PNS
1 stop5h 15mSouthwest
dim. 6/82:40 pmPNS - MDW
Nonstop2h 15mSouthwest
Deal found 4/13$187
This Delta deal was found by Cheapflights users on 4/14. 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.
mer. 5/146:00 amMDW - MCO
1 stop4h 45mDelta
mer. 5/143:45 pmMCO - MDW
1 stop6h 43mDelta
Deal found 4/14$191
This Delta deal was found by Cheapflights users on 4/14. 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.
mer. 6/1810:26 amMDW - PNS
1 stop6h 32mDelta
jeu. 6/264:07 pmPNS - MDW
1 stop5h 38mDelta
Deal found 4/14$197
This Delta deal was found by Cheapflights users on 4/14. 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.
mer. 5/1410:25 amMDW - TPA
1 stop5h 08mDelta
mer. 5/218:30 amTPA - MDW
1 stop4h 23mDelta
Deal found 4/14$197
This Southwest deal was found by Cheapflights users on 4/14. 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.
dim. 5/118:50 pmMDW - RSW
Nonstop2h 45mSouthwest
jeu. 5/155:10 amRSW - MDW
Nonstop3h 00mSouthwest
Deal found 4/14$198
This Frontier deal was found by Cheapflights users on 4/14. 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.
ven. 4/2511:00 amMDW - FLL
1 stop9h 33mFrontier
ven. 5/210:30 pmFLL - MDW
1 stop12h 03mFrontier
Deal found 4/14$198

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 avril 15, 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

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

dim. 5/4

4:00 pm-7:43 pm

Nonstop2h 43m

Tampa

jeu. 5/8

8:48 pm-10:40 pm

Nonstop2h 52m

$100

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

ven. 5/9

1:19 pm-5:03 pm

Nonstop2h 44m

Orlando

dim. 5/11

3:33 pm-5:30 pm

Nonstop2h 57m

$125

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

mar. 5/27

6:55 am-10:25 am

Nonstop2h 30m

Tampa

mar. 6/3

7:25 am-9:10 am

Nonstop2h 45m

$159

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

mar. 6/24

8:45 pm-12:45 am

Nonstop3h 00m

Fort Lauderdale

mer. 6/25

6:50 am-8:55 am

Nonstop3h 05m

$171

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

mer. 5/14

5:10 pm-9:05 pm

Nonstop2h 55m

Miami

mer. 5/21

7:00 am-9:10 am

Nonstop3h 10m

$177

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

mer. 5/14

7:10 am-10:40 am

Nonstop2h 30m

Orlando

mer. 5/21

6:25 pm-8:15 pm

Nonstop2h 50m

$177

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

mer. 6/4

4:55 pm-10:10 pm

1 stop5h 15m

Pensacola

dim. 6/8

2:40 pm-4:55 pm

Nonstop2h 15m

$187

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

mer. 5/14

6:00 am-11:45 am

1 stop4h 45m

Orlando

mer. 5/14

3:45 pm-9:28 pm

1 stop6h 43m

$191

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

mer. 5/14

10:25 am-4:33 pm

1 stop5h 08m

Tampa

sam. 5/17

4:20 pm-9:14 pm

1 stop5h 54m

$197

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

mer. 6/18

10:26 am-4:58 pm

1 stop6h 32m

Pensacola

jeu. 6/26

4:07 pm-9:45 pm

1 stop5h 38m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 60 results
1
2
3
...
6

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 avril 15, 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 avril 15, 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
4,279 reviews

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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
7,917 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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
4,279 reviews

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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
3,281 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Food

7.1

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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 $60 on Frontier. Other airlines that offer cheap prices include Southwest from $80 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 $216 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 $178.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Florida

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Seattle flights
O'Hare Intl to Newark flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Denver flights
O'Hare Intl to Boston flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Los Angeles flights
Midway to Las Vegas flights
Midway to Newark flights
Midway to John F Kennedy Intl flights
O'Hare Intl to San Francisco flights
O'Hare Intl to San Diego flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Hobby flights
O'Hare Intl to Tampa flights
O'Hare Intl to Nashville flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Portland flights
O'Hare Intl to Charlotte flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Charleston flights
O'Hare Intl to Austin flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Salt Lake City flights
Midway to Miami flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Ontario flights
Midway to San Francisco flights
O'Hare Intl to Raleigh flights
O'Hare Intl to Burbank flights
O'Hare Intl to Savannah flights
Midway to Sky Harbor Intl flights
Midway to Seattle flights
Midway to Atlanta flights
Midway to LaGuardia flights
Midway to Orlando flights
Midway to Los Angeles flights
O'Hare Intl to San Antonio 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 avril 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$205FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$84Average$193FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$95Average$334FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$180Average$407FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$391FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$270Average$440FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.