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Midway

$71+ Cheap flights from Florida to Midway (MDW)

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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Florida to Midway

Keep the following information in mind while searching for Florida to Midway flight deals. Data was last updated June 12, 2025.

Round-trip from

$126
(Cheapflightsfares)

One-way from

$71
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$221

Good round-trip deal

$86 or less

Good one-way deal

$81 or less
From Florida to Chicago Midway
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One-way flight from Florida to Chicago Midway
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Highest demand for flights based on searches. 7% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 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 Florida to Chicago Midway.
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Price to beat on a one-way flight from Florida to Chicago Midway.
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Find flight deals from Florida to Midway

Cheapest flights from Florida to Midway
Explore the most affordable flight options available from Florida to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/308:00 amMCO - MDW
Nonstop2h 54mFrontier
Fri 9/58:34 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 6/11$126
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Thu 8/215:01 amTPA - MDW
1 stop6h 07mFrontier
Mon 8/259:10 amMDW - TPA
1 stop5h 13mFrontier
Deal found 6/9$143
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.
Tue 8/52:50 pmTPA - MDW
Nonstop2h 35mSouthwest
Tue 8/126:10 pmMDW - TPA
Nonstop2h 40mSouthwest
Deal found 6/10$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.
Sat 8/234:25 pmRSW - MDW
Nonstop2h 50mSouthwest
Tue 8/269:05 amMDW - RSW
Nonstop2h 45mSouthwest
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.
Fri 8/156:35 amFLL - MDW
Nonstop3h 00mSouthwest
Wed 8/208:25 amMDW - FLL
Nonstop3h 00mSouthwest
Deal found 6/11$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.
Fri 8/157:35 amMCO - MDW
Nonstop2h 45mSouthwest
Tue 8/197:55 pmMDW - MCO
Nonstop2h 35mSouthwest
Deal found 6/11$158
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/96:53 pmMIA - MDW
Nonstop3h 15mFrontier
Mon 10/1310:03 pmMDW - MIA
Nonstop3h 00mFrontier
Deal found 6/10$160
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.
Sat 7/125:45 amMIA - MDW
Nonstop3h 05mSouthwest
Sun 7/138:45 pmMDW - MIA
Nonstop3h 05mSouthwest
Deal found 6/10$177
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.
Tue 8/125:00 pmPNS - MDW
1 stop4h 49mDelta
Wed 8/206:04 amMDW - PNS
1 stop4h 46mDelta
Deal found 6/10$177
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/78:05 pmFLL - MDW
1 stop17h 16mAllegiant Air
Mon 8/111:11 pmMDW - FLL
1 stop5h 02mAllegiant Air
Deal found 6/11$180
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.
Thu 8/1412:30 pmPNS - MDW
1 stop5h 05mSouthwest
Mon 8/185:25 amMDW - PNS
2 stops6h 20mSouthwest
Deal found 6/11$182
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/306:00 amFLL - MDW
1 stop5h 40mFrontier
Tue 8/511:39 amMDW - FLL
1 stop6h 07mFrontier
Deal found 6/10$191

Cheapflights Fare Finder

Customize your flight search to find flights from Florida to Midway 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 June 12, 2025.
Use the filters below to find and compare flights from Florida to Chicago Midway Airport that are best for you.

Fly from

Florida

Fly to

Midway

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 8/30

8:00 am-9:54 am

Nonstop2h 54m

Chicago Midway

Fri 9/5

8:34 am-12:15 pm

Nonstop2h 41m

$126

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 8/21

5:01 am-10:08 am

1 stop6h 07m

Chicago Midway

Mon 8/25

9:10 am-3:23 pm

1 stop5h 13m

$143

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 8/5

2:50 pm-4:25 pm

Nonstop2h 35m

Chicago Midway

Tue 8/12

6:10 pm-9:50 pm

Nonstop2h 40m

$157

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 8/23

4:25 pm-6:15 pm

Nonstop2h 50m

Chicago Midway

Tue 8/26

9:05 am-12:50 pm

Nonstop2h 45m

$157

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Fri 8/15

6:35 am-8:35 am

Nonstop3h 00m

Chicago Midway

Wed 8/20

8:25 am-12:25 pm

Nonstop3h 00m

$158

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 8/15

7:35 am-9:20 am

Nonstop2h 45m

Chicago Midway

Tue 8/19

7:55 pm-11:30 pm

Nonstop2h 35m

$158

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 10/9

6:53 pm-9:08 pm

Nonstop3h 15m

Chicago Midway

Mon 10/13

10:03 pm-2:03 am

Nonstop3h 00m

$160

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Tue 8/12

5:00 pm-9:49 pm

1 stop4h 49m

Chicago Midway

Wed 8/20

6:04 am-10:50 am

1 stop4h 46m

$177

MiamiChicago

MIA - MDW

MIAMDW

Miami

Sat 7/12

5:45 am-7:50 am

Nonstop3h 05m

Chicago Midway

Sun 7/13

8:45 pm-12:50 am

Nonstop3h 05m

$177

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Thu 8/7

8:05 pm-12:21 pm

1 stop17h 16m

Chicago Midway

Mon 8/11

1:11 pm-7:13 pm

1 stop5h 02m

$180

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 Florida to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Florida 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 Florida to Chicago Midway Airport

What is the cheapest month to book a flight from Florida to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Florida to Chicago Midway Airport (average of $160). Flying from Florida to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 FL to MDW?

Find hourly flight availability from Florida to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Florida to Chicago Midway Airport as you normally would.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated June 12, 2025.
Read through reviews of airlines operating flights from Florida to Chicago, such as Southwest, Delta and Allegiant Air. In addition to providing an overall rating, 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

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Allegiant Air
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.9
Fair
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Florida to Midway. 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 Florida to Chicago Midway Airport one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $71. Users have also found prices from $79 and $88 on Southwest and Allegiant Air, respectively.

  • What are the most popular routes from Florida to Chicago Midway Airport?

    While some choose either Tampa - Chicago Midway or Miami - Chicago Midway, Orlando - Chicago Midway is the most popular route from Florida to Chicago Midway Airport.

  • What are the cheapest flights from Florida to Chicago Midway Airport?

    While on average a flight from Florida to Chicago Midway Airport is generally $221, our data shows the cheapest flight currently is $88. When looking at the most popular route, (Orlando - Chicago Midway), you can expect to pay $136 for that flight.

  • Can I find deals for flights from Florida to Midway that include hotel bookings?

    Yes. In addition to deals on Florida to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Florida to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Florida to Midway.

  • Can I find deals for business class flights from Florida to Midway?

    Yes. Cheapflights offers flight deals from Florida to Midway 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 Florida to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Florida to Chicago Midway Airport (average of $160). Flying from Florida to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Florida?

Book flights to Florida if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Florida to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Reagan-National to Midway flights
Pittsburgh to O'Hare Intl flights

Top 4 airlines flying from Florida to Midway

Discover the top 4 airlines that operate flights from Florida to Midway. 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$67Average$196FlexibilityNo cancel feeOn-time65%
FrontierCheapest$70Average$194FlexibilityNo cancel feeOn-time62%
DeltaCheapest$138Average$369FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$160Average$358FlexibilityNo cancel feeOn-time63%

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