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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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — MDW
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap 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 27, 2026.

This Super.com deal was found by Cheapflights users on 1/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1911:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Sun 3/16:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/26$72
This Frontier deal was found by Cheapflights users on 1/25. 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 2/1911:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Sun 2/226:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/25$73
This Super.com deal was found by Cheapflights users on 1/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1412:49 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Sun 2/157:30 am
MDW
-
MCO
Nonstop2h 50m
Frontier
Deal found 1/25$75
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1211:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Sun 2/156:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/26$76
This Super.com deal was found by Cheapflights users on 1/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1211:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Thu 2/196:15 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/25$79
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/511:28 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Sun 3/86:00 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/26$80
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Sun 2/157:30 am
MDW
-
MCO
Nonstop2h 50m
Frontier
Deal found 1/26$88
This CheapOair deal was found by Cheapflights users on 1/25. 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.
Sat 2/1412:49 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Mon 2/169:22 pm
MDW
-
MCO
Nonstop2h 47m
Frontier
Deal found 1/25$90
This Frontier deal was found by Cheapflights users on 1/25. 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 3/1211:13 am
MIA
-
MDW
Nonstop3h 28m
Frontier
Mon 3/166:00 am
MDW
-
MIA
Nonstop3h 13m
Frontier
Deal found 1/25$91
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Fri 2/1312:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Sun 2/157:30 am
MDW
-
MCO
Nonstop2h 50m
Frontier
Deal found 1/25$93
This Frontier deal was found by Cheapflights users on 1/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:49 pm
MCO
-
MDW
Nonstop3h 03m
Frontier
Mon 2/97:00 pm
MDW
-
MCO
Nonstop2h 48m
Frontier
Deal found 1/27$94
This Super.com deal was found by Cheapflights users on 1/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Mon 2/239:22 pm
MDW
-
MCO
Nonstop2h 47m
Frontier
Deal found 1/27$97

Find flight deals from Florida to Midway

Keep the following information in mind while searching for Florida to Midway flight deals. Data was last updated January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$72
(Super.com)

One-way from

$52
(Mytrip)

Popular in

June

Cheapest in

September

Average price

$168

Good round-trip deal

$102 or less

Good one-way deal

$109 or less
Provider with most accurate pricing for Orlando (ORL)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Chicago (CHI) flights.
Search Deals
From Florida to Chicago Midway
Search Deals
One-way flight from Florida to Chicago Midway
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Florida to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Florida to Chicago Midway.
Search Deals

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 January 27, 2026.
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

Fri 4/24

6:05 am-8:04 am

Nonstop2h 59m

Chicago Midway

Sun 4/26

9:14 am-1:03 pm

Nonstop2h 49m

$113

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 2/19

12:20 pm-2:26 pm

Nonstop3h 06m

Chicago Midway

Mon 2/23

9:22 pm-1:09 am

Nonstop2h 47m

$114

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 2/13

12:20 pm-2:26 pm

Nonstop3h 06m

Chicago Midway

Mon 2/16

9:22 pm-1:09 am

Nonstop2h 47m

$127

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 2/24

7:25 am-9:20 am

Nonstop2h 55m

Chicago Midway

Tue 2/24

3:15 pm-6:50 pm

Nonstop2h 35m

$157

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 2/24

7:25 am-9:20 am

Nonstop2h 55m

Chicago Midway

Tue 3/3

3:15 pm-6:50 pm

Nonstop2h 35m

$157

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 3/18

3:25 pm-10:19 pm

1 stop7h 54m

Chicago Midway

Wed 3/25

11:19 am-3:04 pm

Nonstop2h 45m

$170

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 3/7

7:55 pm-9:55 pm

Nonstop3h 00m

Chicago Midway

Sun 3/8

6:40 pm-10:15 pm

Nonstop2h 35m

$177

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 2/25

7:25 am-9:20 am

Nonstop2h 55m

Chicago Midway

Fri 2/27

8:40 pm-12:20 am

Nonstop2h 40m

$177

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Tue 5/5

2:56 pm-7:31 pm

1 stop5h 35m

Chicago Midway

Thu 5/7

2:20 pm-12:45 am

1 stop9h 25m

$180

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 2/24

9:50 am-1:10 pm

1 stop4h 20m

Chicago Midway

Tue 3/3

5:40 pm-9:15 pm

Nonstop2h 35m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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, March is the cheapest month in which you can book a flight from Florida to Chicago Midway Airport (average of $43). Flying from Florida to Chicago Midway Airport in July is currently the most expensive (average of $126). 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 27, 2026.

When flying from Florida to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 15% versus a flight at noon.

What is the cheapest day to fly from Florida to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Florida to Midway. Price data was last updated on January 24, 2026.

Travelers seeking maximum savings on their Florida to Chicago Midway Airport flight should consider departing on Sunday at noon when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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.

  • How long is the flight from Florida to Chicago Midway Airport?

    There are many flights that can get you from Florida to Chicago Midway Airport in 2h 55m. Fly via Frontier, Southwest, or Delta to get the fastest option. There are 990 mi between Florida and Chicago Midway Airport. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Florida to Chicago Midway Airport one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $37. Users have also found prices from $44 and $62 on Frontier and Allegiant Air, respectively.

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

    While some choose either Miami - Chicago Midway or Fort Lauderdale - Chicago Midway, Orlando - Chicago Midway is the most popular route from Florida to Chicago Midway Airport.

  • What are the most reliable airlines from Florida to Chicago Midway Airport?

    The top 3 most reliable airlines when flying from Florida to Chicago Midway Airport are Southwest (73%), Frontier (70%) and Volaris (68%).

  • What are the cheapest flights from Florida to Chicago Midway Airport?

    While on average a flight from Florida to Chicago Midway Airport is generally $161, our data shows the cheapest flight currently is $53. When looking at the most popular route, (Orlando - Chicago Midway), you can expect to pay $111 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, March is the cheapest month in which you can book a flight from Florida to Chicago Midway Airport (average of $43). Flying from Florida to Chicago Midway Airport in July is currently the most expensive (average of $126). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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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John F Kennedy Intl to Midway flights
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Los Angeles to Midway flights
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Charlotte to O'Hare Intl flights
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Santa Ana to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Atlanta to Midway flights
San Francisco to Midway flights
Hobby to Midway flights
Dulles Intl to Midway flights
Miami to O'Hare Intl flights
LaGuardia to Midway flights
Minneapolis to O'Hare Intl flights
Baltimore to Midway flights
Hartford to O'Hare Intl flights
Hobby to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Philadelphia to Midway flights
Reagan-National to Midway flights
Love Field to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Tampa to O'Hare Intl flights
Orlando to O'Hare Intl flights
Minneapolis to Midway flights
San Diego to O'Hare Intl flights
Columbus to O'Hare Intl flights
Sacramento to O'Hare Intl flights
San Jose to O'Hare Intl flights
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San Antonio to O'Hare Intl flights

Top 3 airlines flying from Florida to Midway

Discover the top 3 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 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$183FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$293FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$149Average$340FlexibilityNo cancel feeOn-time63%

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