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Midway

$54+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — MDW
Dec 24 — Dec 311
Tue 12/24
Tue 12/31
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 December 19, 2024.

Round-trip from

$106
(Cheapflightsfares)

One-way from

$54
(Cheapflightsfares)
From Florida to Chicago Midway
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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 December 19, 2024.

This FlightHub deal was found by Cheapflights users on 12/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/318:46 pmTPA - MDW
Nonstop2h 47mFrontier
Sat 1/117:35 amMDW - TPA
1 stop10h 21mFrontier
Deal found 12/18$126
This Frontier deal was found by Cheapflights users on 12/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2412:43 pmMIA - MDW
Nonstop3h 30mFrontier
Mon 1/62:20 pmMDW - MIA
1 stop8h 26mFrontier
Deal found 12/18$153
This Frontier deal was found by Cheapflights users on 12/17. 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 12/314:00 pmMCO - MDW
Nonstop2h 54mFrontier
Thu 1/93:04 pmMDW - MCO
1 stop8h 17mFrontier
Deal found 12/17$184
This eDestinos deal was found by Cheapflights users on 12/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3111:06 amMIA - MDW
2 stops37h 14mMultiple Airlines
Mon 1/68:20 amMDW - MIA
1 stop13h 47mMultiple Airlines
Deal found 12/18$227
This Southwest deal was found by Cheapflights users on 12/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/317:10 pmTPA - MDW
Nonstop2h 40mSouthwest
Thu 1/91:20 pmMDW - TPA
Nonstop2h 35mSouthwest
Deal found 12/18$256
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/255:35 pmFLL - MDW
1 stop5h 31mDelta
Tue 12/315:51 pmMDW - FLL
1 stop5h 24mDelta
Deal found 12/18$292
This Delta deal was found by Cheapflights users on 12/17. 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 12/245:15 pmMCO - MDW
1 stop5h 51mDelta
Tue 12/319:30 amMDW - MCO
1 stop6h 29mDelta
Deal found 12/17$292
This Frontier deal was found by Cheapflights users on 12/17. 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 12/306:35 pmFLL - MDW
1 stop5h 39mFrontier
Tue 12/317:45 amMDW - FLL
1 stop12h 18mFrontier
Deal found 12/17$308
This Trip.com deal was found by Cheapflights users on 12/17. 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.
Sat 12/2810:21 pmRSW - MDW
1 stop9h 18mFrontier
Mon 12/309:59 pmMDW - RSW
1 stop9h 21mFrontier
Deal found 12/17$308
This Southwest deal was found by Cheapflights users on 12/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/258:00 amFLL - MDW
Nonstop3h 10mSouthwest
Tue 12/3111:15 amMDW - FLL
1 stop6h 45mSouthwest
Deal found 12/18$323
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:00 amTPA - MDW
1 stop4h 23mDelta
Tue 1/710:57 amMDW - TPA
1 stop4h 45mDelta
Deal found 12/18$327
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/314:52 pmRSW - MDW
1 stop6h 14mDelta
Tue 1/710:57 amMDW - RSW
1 stop5h 08mDelta
Deal found 12/18$332

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 December 19, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 2/19

9:08 pm-11:00 pm

Nonstop2h 52m

Chicago Midway

Wed 2/26

4:20 pm-8:03 pm

Nonstop2h 43m

$106

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 1/11

4:59 pm-11:29 pm

1 stop7h 30m

Chicago Midway

Mon 1/13

4:28 pm-1:48 am

1 stop8h 20m

$108

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 2/20

3:52 pm-6:20 pm

Nonstop3h 28m

Chicago Midway

Sun 2/23

4:19 pm-8:30 pm

Nonstop3h 11m

$116

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 2/4

5:55 pm-7:45 pm

Nonstop2h 50m

Chicago Midway

Mon 2/10

5:25 am-9:05 am

Nonstop2h 40m

$164

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Sat 1/18

7:15 am-9:30 am

Nonstop3h 15m

Chicago Midway

Mon 1/20

7:35 pm-11:30 pm

Nonstop2h 55m

$164

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 2/21

6:45 am-8:45 am

Nonstop3h 00m

Chicago Midway

Sat 2/22

7:20 pm-11:10 pm

Nonstop2h 50m

$164

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 1/23

7:50 pm-9:45 pm

Nonstop2h 55m

Chicago Midway

Tue 1/28

1:20 pm-4:55 pm

Nonstop2h 35m

$164

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 1/6

1:30 pm-4:14 pm

1 stop27h 44m

Chicago Midway

Wed 1/8

6:52 pm-3:25 pm

1 stop19h 33m

$165

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Wed 1/15

9:17 am-5:57 pm

1 stop9h 40m

Chicago Midway

Sat 1/18

7:30 am-7:53 pm

1 stop11h 23m

$188

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 2/22

5:17 pm-12:17 am

1 stop8h 00m

Chicago Midway

Sat 3/1

6:40 am-4:26 pm

1 stop8h 46m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

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 October is currently the most expensive (average of $232). 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 December 19, 2024.

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 December 19, 2024.
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
4,836 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,836 reviews
Southwest
8.1
Very good
4,836 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,600 reviews
Southwest
8.1
Very good
4,836 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

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
4,836 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Allegiant Air
7.4
Good
829 reviews
Southwest
8.1
Very good
4,836 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Frontier
6.1
Okay
3,478 reviews
Southwest
8.1
Very good
4,836 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

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 $54. Users have also found prices from $79 and $98 on Southwest and Delta, respectively.

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

    While some choose either Miami - Chicago Midway or Tampa - 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 $172, our data shows the cheapest flight currently is $54. When looking at the most popular route, (Orlando - Chicago Midway), you can expect to pay $108 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 October is currently the most expensive (average of $232). 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.

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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 December 19, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$174FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$156FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$158Average$383FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$382FlexibilityNo cancel feeOn-timeN/A
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