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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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIA
sty 25 — lut 11
sob. 1/25
sob. 2/1
1 adult, Economy
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Cheap flight deals from Midway to Florida

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Florida (USFL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated Styczeń 20, 2025.

Round-trip from

$91
(Frontier)

One-way from

$53
(Trip.com)
From Chicago Midway to Florida
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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 Styczeń 20, 2025.

This Frontier deal was found by Cheapflights users on 1/19. 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.
sob. 3/14:19 pmMDW - TPA
Nonstop2h 43mFrontier
pon. 3/37:18 pmTPA - MDW
Nonstop2h 56mFrontier
Deal found 1/19$91
This FlightHub deal was found by Cheapflights users on 1/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
śr. 2/197:25 amMDW - MIA
Nonstop3h 12mFrontier
sob. 2/226:25 amMIA - MDW
1 stop18h 52mFrontier
Deal found 1/20$107
This Cheapflightsfares deal was found by Cheapflights users on 1/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sob. 3/112:43 pmMDW - MCO
Nonstop2h 48mFrontier
pon. 3/37:51 pmMCO - MDW
1 stop5h 07mFrontier
Deal found 1/19$127
This Frontier deal was found by Cheapflights users on 1/20. 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.
sob. 3/16:40 amMDW - RSW
1 stop8h 46mFrontier
czw. 3/612:42 pmRSW - MDW
1 stop12h 35mFrontier
Deal found 1/20$130
This Southwest deal was found by Cheapflights users on 1/20. 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.
ndz. 2/238:25 pmMDW - FLL
Nonstop3h 00mSouthwest
czw. 2/276:30 amFLL - MDW
Nonstop3h 15mSouthwest
Deal found 1/20$169
This Southwest deal was found by Cheapflights users on 1/20. 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.
sob. 2/223:00 pmMDW - PBI
1 stop6h 00mSouthwest
śr. 2/262:10 pmPBI - MDW
1 stop8h 15mSouthwest
Deal found 1/20$179
This eDestinos deal was found by Cheapflights users on 1/20. 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.
śr. 3/125:58 pmMDW - FLL
1 stop16h 25mFrontier
pon. 3/1710:22 pmFLL - MDW
2 stops18h 31mFrontier
Deal found 1/20$180
This eDestinos deal was found by Cheapflights users on 1/20. 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.
śr. 3/129:25 amMDW - FLL
2 stops9h 50mMultiple Airlines
pon. 3/1710:22 pmFLL - MDW
2 stops18h 31mMultiple Airlines
Deal found 1/20$196
This Delta deal was found by Cheapflights users on 1/20. 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.
śr. 2/195:05 pmMDW - TPA
1 stop6h 21mDelta
śr. 2/267:00 amTPA - MDW
1 stop5h 59mDelta
Deal found 1/20$197
This Southwest deal was found by Cheapflights users on 1/19. 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.
ndz. 2/236:00 amMDW - RSW
Nonstop3h 00mSouthwest
pt. 2/286:45 amRSW - MDW
Nonstop3h 00mSouthwest
Deal found 1/19$209
This Southwest deal was found by Cheapflights users on 1/19. 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.
wt. 2/46:10 pmMDW - TPA
Nonstop2h 35mSouthwest
śr. 2/127:15 amTPA - MDW
Nonstop2h 50mSouthwest
Deal found 1/19$213
This Delta deal was found by Cheapflights users on 1/20. 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.
pon. 2/242:08 pmMDW - FLL
1 stop5h 01mDelta
wt. 2/256:30 amFLL - MDW
1 stop6h 29mDelta
Deal found 1/20$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 Styczeń 20, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

sob. 3/1

4:19 pm-8:02 pm

Nonstop2h 43m

Tampa

pon. 3/3

7:18 pm-9:14 pm

Nonstop2h 56m

$91

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

śr. 2/19

7:25 am-11:37 am

Nonstop3h 12m

Miami

sob. 2/22

6:25 am-12:17 am

1 stop18h 52m

$107

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

pon. 2/3

4:27 pm-12:41 am

1 stop7h 14m

Orlando

pt. 2/7

12:38 pm-2:42 pm

Nonstop3h 04m

$127

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

sob. 3/1

6:40 am-4:26 pm

1 stop8h 46m

Fort Myers SW Florida Intl

czw. 3/6

12:42 pm-12:17 am

1 stop12h 35m

$130

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

pon. 2/24

7:35 pm-11:30 pm

Nonstop2h 55m

Fort Lauderdale

czw. 2/27

6:30 am-8:45 am

Nonstop3h 15m

$169

ChicagoWest Palm Beach

MDW - PBI

MDWPBI

Chicago Midway

sob. 2/22

3:00 pm-10:00 pm

1 stop6h 00m

Palm Beach Intl

śr. 2/26

2:10 pm-9:25 pm

1 stop8h 15m

$179

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

śr. 3/12

5:58 pm-11:23 am

1 stop16h 25m

Fort Lauderdale

pon. 3/17

10:22 pm-3:53 pm

2 stops18h 31m

$180

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

czw. 4/10

5:15 am-8:15 pm

1 stop14h 00m

Fort Lauderdale

wt. 4/15

12:14 pm-7:45 pm

1 stop8h 31m

$184

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

śr. 2/19

10:57 am-7:17 pm

1 stop7h 20m

Tampa

śr. 2/26

10:00 am-4:20 pm

1 stop7h 20m

$197

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

ndz. 2/23

6:00 am-10:00 am

Nonstop3h 00m

Fort Myers SW Florida Intl

pt. 2/28

6:45 am-8:45 am

Nonstop3h 00m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

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 $230). 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 Styczeń 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.

Weekly flight availability from Chicago Midway Airport to Florida

Explore weekly flight availability from Midway to Florida. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated Styczeń 20, 2025.

The most flights from MDW to USFL are scheduled on a Saturday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

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 Styczeń 20, 2025.
See what other customers who have flown with Frontier, Delta and Southwest 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
4,659 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Food

7.2

Entertainment

7.7

Reviews

1 / 10

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
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Food

7.2

Entertainment

7.7

Reviews

1 / 10

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
8,521 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Food

7.2

Entertainment

7.7

Reviews

1 / 10

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
7.4
Good
801 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Food

7.2

Entertainment

7.7

Reviews

1 / 10

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
6.1
Okay
3,441 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Food

7.2

Entertainment

7.7

Reviews

1 / 10

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 $53 on Frontier. Other airlines that offer cheap prices include Southwest from $79 and Delta from $99 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 $212 for a flight from Chicago Midway Airport to Florida. The cheapest flight overall is $37 while the most popular route, (Chicago Midway - Orlando) is currently priced at $109.

  • 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 $230). 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.

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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 New Orleans flights
O'Hare Intl to Burbank 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 Styczeń 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$55Average$206FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$65Average$211FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$95Average$343FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$168Average$417FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$178Average$440FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$410FlexibilityNo cancel feeOn-timeN/A
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