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Midway

$52+ 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 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — MDW
abr. 2 — abr. 91
mié. 4/2
mié. 4/9
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 marzo 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$101
(eDestinos)

One-way from

$52
(Trip.com)

Popular in

December

Cheapest in

May

Average price

$216

Good round-trip deal

$115 or less

Good one-way deal

$94 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. 11% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in March 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 marzo 28, 2025.

This eDestinos deal was found by Cheapflights users on 3/26. 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.
vie. 4/2510:30 amMCO - MDW
Nonstop3h 01mFrontier
dom. 4/278:00 amMDW - MCO
Nonstop2h 51mFrontier
Deal found 3/26$101
This FlightHub deal was found by Cheapflights users on 3/27. 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.
jue. 4/39:51 amTPA - MDW
Nonstop2h 52mFrontier
sáb. 4/54:10 pmMDW - TPA
Nonstop2h 40mFrontier
Deal found 3/27$106
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
mar. 4/811:03 amMIA - MDW
Nonstop3h 28mFrontier
mar. 4/156:00 amMDW - MIA
Nonstop3h 08mFrontier
Deal found 3/27$121
This Southwest deal was found by Cheapflights users on 3/27. 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.
sáb. 5/105:05 amMIA - MDW
Nonstop3h 10mSouthwest
mar. 5/135:10 pmMDW - MIA
Nonstop2h 55mSouthwest
Deal found 3/27$177
This Southwest deal was found by Cheapflights users on 3/27. 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. 6/32:40 pmMCO - MDW
1 stop5h 50mSouthwest
sáb. 6/75:45 pmMDW - MCO
Nonstop2h 45mSouthwest
Deal found 3/27$195
This Southwest deal was found by Cheapflights users on 3/27. 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.
sáb. 6/144:05 pmTPA - MDW
1 stop6h 45mSouthwest
mar. 6/179:10 pmMDW - TPA
Nonstop2h 40mSouthwest
Deal found 3/27$196
This Southwest deal was found by Cheapflights users on 3/27. 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.
sáb. 5/36:25 amFLL - MDW
Nonstop3h 10mSouthwest
mié. 5/76:35 pmMDW - FLL
Nonstop2h 55mSouthwest
Deal found 3/27$197
This Delta deal was found by Cheapflights users on 3/27. 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.
mar. 7/228:30 amMCO - MDW
1 stop5h 00mDelta
mar. 8/53:40 pmMDW - MCO
1 stop5h 06mDelta
Deal found 3/27$201
This Southwest deal was found by Cheapflights users on 3/27. 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.
mié. 8/66:40 amPBI - MDW
2 stops6h 25mSouthwest
mar. 8/128:35 amMDW - PBI
1 stop5h 55mSouthwest
Deal found 3/27$204
This Southwest deal was found by Cheapflights users on 3/27. 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.
jue. 6/57:55 pmECP - MDW
1 stop5h 10mSouthwest
lun. 6/91:00 pmMDW - ECP
Nonstop2h 05mSouthwest
Deal found 3/27$207
This Delta deal was found by Cheapflights users on 3/27. 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.
sáb. 5/105:35 amMIA - MDW
1 stop7h 33mDelta
dom. 5/119:20 amMDW - MIA
1 stop7h 47mDelta
Deal found 3/27$216
This Delta deal was found by Cheapflights users on 3/27. 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.
sáb. 5/36:25 pmFLL - MDW
1 stop4h 57mDelta
mié. 5/79:20 amMDW - FLL
1 stop4h 54mDelta
Deal found 3/27$217

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 marzo 28, 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

vie. 4/25

10:30 am-12:31 pm

Nonstop3h 01m

Chicago Midway

dom. 4/27

8:00 am-11:51 am

Nonstop2h 51m

$101

TampaChicago

TPA - MDW

TPAMDW

Tampa

jue. 4/3

9:51 am-11:43 am

Nonstop2h 52m

Chicago Midway

sáb. 4/5

4:10 pm-7:50 pm

Nonstop2h 40m

$106

MiamiChicago

MIA - MDW

MIAMDW

Miami

mar. 4/8

11:03 am-1:31 pm

Nonstop3h 28m

Chicago Midway

mar. 4/15

6:00 am-10:08 am

Nonstop3h 08m

$121

MiamiChicago

MIA - MDW

MIAMDW

Miami

sáb. 5/10

5:05 am-7:15 am

Nonstop3h 10m

Chicago Midway

dom. 5/11

8:40 pm-12:40 am

Nonstop3h 00m

$177

TampaChicago

TPA - MDW

TPAMDW

Tampa

mar. 5/13

8:50 am-2:35 pm

1 stop6h 45m

Chicago Midway

mar. 5/13

3:45 pm-7:20 pm

Nonstop2h 35m

$193

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

mar. 6/3

2:40 pm-7:30 pm

1 stop5h 50m

Chicago Midway

sáb. 6/7

5:45 pm-9:30 pm

Nonstop2h 45m

$195

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

sáb. 5/3

6:25 am-8:35 am

Nonstop3h 10m

Chicago Midway

mié. 5/7

6:35 pm-10:30 pm

Nonstop2h 55m

$197

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

mié. 8/6

6:40 am-12:05 pm

2 stops6h 25m

Chicago Midway

mar. 8/12

8:35 am-3:30 pm

1 stop5h 55m

$204

Panama CityChicago

ECP - MDW

ECPMDW

Panama City NW Florida Beaches

jue. 6/5

7:55 pm-1:05 am

1 stop5h 10m

Chicago Midway

lun. 6/9

1:00 pm-3:05 pm

Nonstop2h 05m

$207

MiamiChicago

MIA - MDW

MIAMDW

Miami

sáb. 5/10

5:35 am-12:08 pm

1 stop7h 33m

Chicago Midway

dom. 5/11

9:20 am-6:07 pm

1 stop7h 47m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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 marzo 28, 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.

Weekly flight availability from Florida to Chicago Midway Airport

Explore weekly flight availability from Florida to Midway. 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 marzo 28, 2025.

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

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 marzo 28, 2025.
Read through reviews of airlines operating flights from Florida to Chicago, such as Southwest, Delta and Avelo Airlines. 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
4,273 reviews

Crew

8.6

Food

7.1

Entertainment

7.6

Overall

8.1

Comfort

8.1

Boarding

8.2

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
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Food

7.1

Entertainment

7.6

Overall

8.1

Comfort

8.1

Boarding

8.2

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
7,896 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Food

7.1

Entertainment

7.6

Overall

8.1

Comfort

8.1

Boarding

8.2

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.
Avelo Airlines
7.5
Good
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Food

7.1

Entertainment

7.6

Overall

8.1

Comfort

8.1

Boarding

8.2

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
731 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Food

7.1

Entertainment

7.6

Overall

8.1

Comfort

8.1

Boarding

8.2

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
3,271 reviews
Southwest
8.1
Very good
4,273 reviews

Crew

8.6

Food

7.1

Entertainment

7.6

Overall

8.1

Comfort

8.1

Boarding

8.2

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 $52. Users have also found prices from $88 and $91 on Southwest and Allegiant Air, respectively.

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

    While some choose either Miami - Chicago Midway or Orlando - 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 $250, our data shows the cheapest flight currently is $49. When looking at the most popular route, (Tampa - Chicago Midway), you can expect to pay $121 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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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 marzo 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$62Average$155FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$166FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$159Average$370FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$384FlexibilityNo cancel feeOn-timeN/A
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