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Midway

$45+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$80
(Cheapflightsfares)

One-way from

$45
(Trip.com)

Popular in

June

Cheapest in

February

Average price

$138

Good round-trip deal

$90 or less

Good one-way deal

$62 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. 5% potential increase in price ($10 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 February 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 February 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/18. 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.
Tue 2/251:13 pmMCO - MDW
Nonstop2h 59mFrontier
Tue 3/48:30 amMDW - MCO
Nonstop2h 48mFrontier
Deal found 2/18$80
This Cheapflightsfares deal was found by Cheapflights users on 2/18. 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 4/179:51 amTPA - MDW
Nonstop2h 52mFrontier
Sun 4/205:15 amMDW - TPA
Nonstop2h 41mFrontier
Deal found 2/18$81
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/512:42 pmMIA - MDW
Nonstop3h 31mFrontier
Sun 3/97:25 amMDW - MIA
Nonstop3h 12mFrontier
Deal found 2/19$92
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.
Thu 5/89:05 amFLL - MDW
1 stop5h 29mFrontier
Mon 5/128:30 amMDW - FLL
1 stop12h 00mFrontier
Deal found 2/19$110
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/311:21 amVPS - MDW
Nonstop2h 13mAllegiant Air
Sun 4/62:24 pmMDW - VPS
Nonstop2h 10mAllegiant Air
Deal found 2/20$134
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.
Mon 5/510:11 amRSW - MDW
1 stop8h 17mFrontier
Fri 5/1612:15 pmMDW - RSW
1 stop8h 07mFrontier
Deal found 2/20$140
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 3/267:05 amTPA - MDW
Nonstop2h 50mSouthwest
Tue 4/83:45 pmMDW - TPA
Nonstop2h 35mSouthwest
Deal found 2/20$193
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/279:05 amMCO - MDW
2 stops13h 24mMultiple Airlines
Mon 3/312:43 pmMDW - MCO
Nonstop2h 48mMultiple Airlines
Deal found 2/19$195
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.
Wed 4/306:00 amTPA - MDW
1 stop4h 07mDelta
Wed 4/303:02 pmMDW - TPA
1 stop4h 47mDelta
Deal found 2/20$209
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 3/254:10 pmMCO - MDW
1 stop7h 13mDelta
Wed 3/2612:51 pmMDW - MCO
1 stop5h 52mDelta
Deal found 2/20$209
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.
Thu 5/18:55 pmFLL - MDW
Nonstop3h 10mSouthwest
Wed 5/76:35 pmMDW - FLL
Nonstop2h 55mSouthwest
Deal found 2/20$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.
Sat 3/156:10 pmPBI - MDW
1 stop5h 17mDelta
Tue 3/186:00 amMDW - PBI
1 stop7h 27mDelta
Deal found 2/20$217

Find flights from Florida to Midway within your budget

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 February 20, 2025.

Fly from

Florida

Fly to

Midway

Route

Depart

Return

Price

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 4/17

9:51 am-11:43 am

Nonstop2h 52m

Chicago Midway

Sun 4/20

5:15 am-8:56 am

Nonstop2h 41m

$81

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 3/4

1:13 pm-3:12 pm

Nonstop2h 59m

Chicago Midway

Sat 3/8

9:48 am-1:33 pm

Nonstop2h 45m

$90

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 3/5

12:42 pm-3:13 pm

Nonstop3h 31m

Chicago Midway

Sun 3/9

7:25 am-11:37 am

Nonstop3h 12m

$92

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Thu 5/8

9:05 am-1:34 pm

1 stop5h 29m

Chicago Midway

Mon 5/12

8:30 am-9:30 pm

1 stop12h 00m

$110

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Thu 4/3

11:21 am-1:34 pm

Nonstop2h 13m

Chicago Midway

Sun 4/6

2:24 pm-4:34 pm

Nonstop2h 10m

$134

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Mon 5/5

10:11 am-5:28 pm

1 stop8h 17m

Chicago Midway

Fri 5/16

12:15 pm-9:22 pm

1 stop8h 07m

$140

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 3/26

7:05 am-8:55 am

Nonstop2h 50m

Chicago Midway

Tue 4/8

3:45 pm-7:20 pm

Nonstop2h 35m

$193

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 4/30

6:00 am-9:07 am

1 stop4h 07m

Chicago Midway

Wed 4/30

3:02 pm-8:49 pm

1 stop4h 47m

$209

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 3/25

4:10 pm-10:23 pm

1 stop7h 13m

Chicago Midway

Wed 3/26

12:51 pm-7:43 pm

1 stop5h 52m

$209

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Thu 5/1

8:55 pm-11:05 pm

Nonstop3h 10m

Chicago Midway

Wed 5/7

6:35 pm-10:30 pm

Nonstop2h 55m

$213

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 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.

Travel insights for flights from Florida to Midway

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

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 February 20, 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 February 20, 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
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

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

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

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
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

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
765 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

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
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Entertainment

7.6

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 $45. Users have also found prices from $69 and $90 on Allegiant Air and Southwest, respectively.

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

    While some choose either Fort Lauderdale - Chicago Midway or Tampa - Chicago Midway, Miami - 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 $159, our data shows the cheapest flight currently is $43. When looking at the most popular route, (Miami - Chicago Midway), you can expect to pay $69 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
New Buffalo
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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LaGuardia to Midway flights
Los Angeles to Midway flights
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Atlanta to O'Hare Intl flights
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Dulles Intl to Midway flights
Charlotte to O'Hare Intl flights
San Francisco to Midway flights
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Miami to O'Hare Intl flights
Seattle to Midway flights
Atlanta to Midway flights
Portland to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to Midway flights
Philadelphia to Midway flights
Tampa to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Hobby to O'Hare Intl flights
Oakland to O'Hare Intl flights
Denver to Midway flights
Hobby to Midway flights
Nashville to O'Hare Intl flights
Hartford 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$61Average$160FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$139FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$158Average$373FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$389FlexibilityNo cancel feeOn-timeN/A
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