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Midway

$59+ 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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — MDW
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$111
(Kiwi.com)

One-way from

$59
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$189

Good round-trip deal

$96 or less

Good one-way deal

$103 or less
Provider with most accurate pricing for Orlando (ORL)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Chicago (CHI) flights.
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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 ($14 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 April 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 April 29, 2025.

This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/266:22 pmMCO - MDW
Nonstop2h 55mFrontier
Mon 6/309:12 pmMDW - MCO
Nonstop2h 41mFrontier
Deal found 4/29$111
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.
Wed 5/287:25 pmTPA - MDW
Nonstop2h 45mSouthwest
Sun 6/19:00 pmMDW - TPA
Nonstop2h 35mSouthwest
Deal found 4/29$169
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.
Thu 5/298:55 pmFLL - MDW
Nonstop3h 10mSouthwest
Mon 6/26:30 pmMDW - FLL
Nonstop2h 55mSouthwest
Deal found 4/29$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.
Wed 7/26:30 amMIA - MDW
Nonstop3h 10mSouthwest
Sat 7/57:10 pmMDW - MIA
Nonstop3h 00mSouthwest
Deal found 4/28$179
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/198:44 pmTPA - MDW
Nonstop2h 48mFrontier
Sun 6/224:06 pmMDW - TPA
Nonstop2h 43mFrontier
Deal found 4/29$181
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 5/296:00 amPNS - MDW
1 stop4h 35mSouthwest
Sun 6/110:45 amMDW - PNS
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.
Thu 5/298:02 pmFLL - MDW
1 stop24h 12mAllegiant Air
Mon 6/28:04 pmMDW - FLL
1 stop13h 23mAllegiant Air
Deal found 4/29$193
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.
Fri 5/304:20 pmTPA - MDW
1 stop6h 07mDelta
Mon 6/26:00 amMDW - TPA
1 stop7h 14mDelta
Deal found 4/29$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.
Tue 6/172:47 pmECP - MDW
1 stop6h 58mDelta
Tue 6/246:00 amMDW - ECP
1 stop6h 42mDelta
Deal found 4/29$197
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.
Tue 6/39:35 amFLL - MDW
1 stop7h 04mFrontier
Fri 6/66:30 amMDW - FLL
1 stop10h 38mFrontier
Deal found 4/28$208
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.
Sat 5/245:50 pmRSW - MDW
Nonstop3h 00mSouthwest
Tue 5/278:45 amMDW - RSW
Nonstop2h 50mSouthwest
Deal found 4/28$208
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/153:55 pmMIA - MDW
1 stop8h 44mFrontier
Mon 5/196:15 amMDW - MIA
1 stop16h 16mFrontier
Deal found 4/28$211

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 April 29, 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

Thu 6/26

6:22 pm-8:17 pm

Nonstop2h 55m

Chicago Midway

Mon 6/30

9:12 pm-12:53 am

Nonstop2h 41m

$111

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 5/28

7:25 pm-9:10 pm

Nonstop2h 45m

Chicago Midway

Sun 6/1

9:00 pm-12:35 am

Nonstop2h 35m

$169

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Thu 5/29

4:10 pm-6:20 pm

Nonstop3h 10m

Chicago Midway

Tue 6/3

6:35 pm-10:30 pm

Nonstop2h 55m

$171

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 7/2

6:30 am-8:40 am

Nonstop3h 10m

Chicago Midway

Sat 7/5

7:10 pm-11:10 pm

Nonstop3h 00m

$179

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 6/19

8:44 pm-10:32 pm

Nonstop2h 48m

Chicago Midway

Sun 6/22

4:06 pm-7:49 pm

Nonstop2h 43m

$181

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 5/29

6:00 am-10:35 am

1 stop4h 35m

Chicago Midway

Sun 6/1

10:45 am-1:00 pm

Nonstop2h 15m

$187

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Thu 5/29

8:02 pm-7:14 pm

1 stop24h 12m

Chicago Midway

Mon 6/2

8:04 pm-10:27 am

1 stop13h 23m

$193

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 5/30

4:20 pm-9:27 pm

1 stop6h 07m

Chicago Midway

Mon 6/2

6:00 am-2:14 pm

1 stop7h 14m

$197

Panama CityChicago

ECP - MDW

ECPMDW

Panama City NW Florida Beaches

Tue 6/17

2:47 pm-9:45 pm

1 stop6h 58m

Chicago Midway

Tue 6/24

6:00 am-12:42 pm

1 stop6h 42m

$197

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Sat 5/31

10:48 pm-9:03 am

1 stop11h 15m

Chicago Midway

Fri 6/6

6:30 am-6:08 pm

1 stop10h 38m

$208

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 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 April 29, 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 April 29, 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
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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
734 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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
6.0
Okay
3,284 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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 $59. Users have also found prices from $80 and $90 on Southwest and Allegiant Air, respectively.

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

    While some choose either Orlando - Chicago Midway or Miami - Chicago Midway, Tampa - 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 $220, our data shows the cheapest flight currently is $98. When looking at the most popular route, (Tampa - Chicago Midway), you can expect to pay $87 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
Hammond
Benton Harbor
Porter
Lansing
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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Detroit 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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$60Average$175FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$196FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$159Average$364FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$384FlexibilityNo cancel feeOn-timeN/A

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