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Midway

$53+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — MDW
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Florida to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Florida (USFL) to Midway (MDW). 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 January 21, 2025.

Round-trip from

$82
(Cheapflightsfares)

One-way from

$53
(Trip.com)

Good round-trip deal

$122 or less

Good one-way deal

$71 or less
From Florida to Chicago Midway
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One-way flight from Florida to Chicago Midway
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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 January 21, 2025.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/18:57 pmTPA - MDW
Nonstop2h 54mFrontier
Wed 3/54:20 pmMDW - TPA
Nonstop2h 43mFrontier
Deal found 1/20$82
This Trip.com deal was found by Cheapflights users on 1/21. 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.
Mon 2/107:15 amMIA - MDW
1 stop14h 50mFrontier
Wed 2/127:25 amMDW - MIA
Nonstop3h 12mFrontier
Deal found 1/21$100
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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.
Fri 2/76:31 pmMCO - MDW
1 stop7h 23mFrontier
Sun 2/910:58 amMDW - MCO
Nonstop2h 47mFrontier
Deal found 1/21$102
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.
Sun 5/118:40 amFLL - MDW
1 stop5h 54mFrontier
Sat 5/176:43 pmMDW - FLL
1 stop11h 57mFrontier
Deal found 1/20$131
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.
Fri 2/218:25 pmTPA - MDW
Nonstop2h 40mSouthwest
Sun 2/238:30 pmMDW - TPA
Nonstop2h 35mSouthwest
Deal found 1/20$169
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.
Thu 2/207:30 amFLL - MDW
Nonstop3h 10mSouthwest
Mon 2/247:35 pmMDW - FLL
Nonstop2h 55mSouthwest
Deal found 1/19$169
This CheapOair deal was found by Cheapflights users on 1/21. 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 2/137:27 pmPNS - MDW
1 stop28h 50mFrontier
Mon 2/176:40 amMDW - PNS
1 stop11h 47mFrontier
Deal found 1/21$175
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/189:00 pmFLL - MDW
1 stop27h 00mMultiple Airlines
Fri 2/216:48 pmMDW - FLL
1 stop15h 45mMultiple Airlines
Deal found 1/19$188
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.
Fri 2/288:30 amTPA - MDW
1 stop5h 35mDelta
Sun 3/22:08 pmMDW - TPA
1 stop7h 34mDelta
Deal found 1/20$197
This Southwest deal was found by Cheapflights users on 1/21. 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 3/127:15 amMCO - MDW
Nonstop3h 00mSouthwest
Wed 3/123:30 pmMDW - MCO
Nonstop2h 40mSouthwest
Deal found 1/21$197
This Delta deal was found by Cheapflights users on 1/21. 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 2/1411:33 amMIA - MDW
1 stop7h 38mDelta
Mon 2/172:08 pmMDW - MIA
1 stop6h 34mDelta
Deal found 1/21$217
This Delta deal was found by Cheapflights users on 1/21. 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.
Thu 2/206:30 amFLL - MDW
1 stop4h 42mDelta
Mon 2/249:33 amMDW - FLL
1 stop5h 17mDelta
Deal found 1/21$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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 3/1

8:57 pm-10:51 pm

Nonstop2h 54m

Chicago Midway

Wed 3/5

4:20 pm-8:03 pm

Nonstop2h 43m

$82

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 2/7

6:31 pm-12:54 am

1 stop7h 23m

Chicago Midway

Sun 2/9

10:58 am-2:45 pm

Nonstop2h 47m

$100

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 2/13

5:42 pm-1:46 pm

1 stop21h 04m

Chicago Midway

Sun 2/16

7:25 am-11:37 am

Nonstop3h 12m

$107

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Sun 5/11

8:40 am-1:34 pm

1 stop5h 54m

Chicago Midway

Sat 5/17

6:43 pm-7:40 am

1 stop11h 57m

$131

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Thu 2/20

7:30 am-9:40 am

Nonstop3h 10m

Chicago Midway

Mon 2/24

7:35 pm-11:30 pm

Nonstop2h 55m

$169

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 2/13

7:27 pm-12:17 am

1 stop28h 50m

Chicago Midway

Mon 2/17

6:40 am-6:27 pm

1 stop11h 47m

$175

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Wed 2/19

4:45 pm-9:25 pm

1 stop5h 40m

Chicago Midway

Wed 2/26

10:15 am-8:20 pm

1 stop9h 05m

$179

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Tue 2/18

9:00 pm-11:00 pm

1 stop27h 00m

Chicago Midway

Fri 2/21

6:48 pm-11:33 am

1 stop15h 45m

$188

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 2/28

8:30 am-1:05 pm

1 stop5h 35m

Chicago Midway

Sun 3/2

2:08 pm-10:42 pm

1 stop7h 34m

$197

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 2/27

6:15 am-10:12 am

1 stop4h 57m

Chicago Midway

Mon 3/3

12:44 pm-7:42 pm

1 stop5h 58m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 58 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 January 21, 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 January 21, 2025.
Read through reviews of airlines operating flights from Florida to Chicago, such as Delta, Frontier and Southwest. 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
4,662 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Avelo Airlines
7.5
Good
74 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Spirit Airlines
6.3
Okay
8,115 reviews
Southwest
8.1
Very good
4,662 reviews

Boarding

8.2

Food

7.2

Overall

8.1

Crew

8.7

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

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 $53. Users have also found prices from $85 and $99 on Southwest and Delta, 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 $211, our data shows the cheapest flight currently is $49. When looking at the most popular route, (Orlando - Chicago Midway), you can expect to pay $76 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$60Average$171FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$165FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$158Average$389FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$382FlexibilityNo cancel feeOn-timeN/A
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