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Midway

$66+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — MDW
May 28 — Jun 41
Thu 5/28
Thu 6/4
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 April 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
Sat 5/22:13 pm
MCO
-
MDW
Nonstop3h 00m
Frontier
Mon 5/48:41 am
MDW
-
MCO
Nonstop2h 51m
Frontier
Deal found 4/25$127
This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
Tue 5/127:00 am
FLL
-
MDW
1 stop16h 02m
Multiple Airlines
Wed 5/1312:04 pm
MDW
-
FLL
1 stop11h 40m
Multiple Airlines
Deal found 4/24$132
This Priceline deal was found by Cheapflights users on 4/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/83:10 pm
MCO
-
MDW
1 stop7h 52m
Frontier
Mon 5/114:52 pm
MDW
-
MCO
Nonstop2h 47m
Frontier
Deal found 4/23$133
This Expedia deal was found by Cheapflights users on 4/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:45 am
MCO
-
MDW
Nonstop2h 56m
Frontier
Tue 5/1912:24 pm
MDW
-
MCO
1 stop8h 23m
Frontier
Deal found 4/24$134
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Tue 5/1211:23 am
MIA
-
MDW
1 stop11h 39m
Frontier
Wed 5/206:00 am
MDW
-
MIA
1 stop9h 27m
Frontier
Deal found 4/27$135
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Wed 5/275:10 pm
MCO
-
MDW
1 stop5h 52m
Frontier
Wed 6/312:04 pm
MDW
-
MCO
1 stop6h 28m
Frontier
Deal found 4/27$135
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Tue 5/128:55 pm
FLL
-
MDW
1 stop15h 14m
Multiple Airlines
Sat 5/166:00 am
MDW
-
FLL
1 stop16h 12m
Multiple Airlines
Deal found 4/27$136
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
Mon 5/1111:06 am
MIA
-
MDW
1 stop25h 03m
Multiple Airlines
Thu 5/146:00 am
MDW
-
MIA
1 stop9h 27m
Multiple Airlines
Deal found 4/23$137
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Tue 5/266:05 am
FLL
-
MDW
1 stop16h 57m
Frontier
Tue 6/212:27 pm
MDW
-
FLL
1 stop11h 17m
Frontier
Deal found 4/28$140
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Tue 5/265:22 pm
MIA
-
MDW
1 stop5h 40m
Frontier
Tue 6/212:27 pm
MDW
-
MIA
1 stop9h 20m
Frontier
Deal found 4/27$140
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Tue 5/269:56 am
MCO
-
MDW
1 stop26h 13m
Frontier
Tue 6/212:27 pm
MDW
-
MCO
1 stop6h 05m
Frontier
Deal found 4/26$140
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Wed 6/311:23 am
MIA
-
MDW
1 stop11h 39m
Frontier
Tue 6/912:27 pm
MDW
-
MIA
1 stop9h 36m
Frontier
Deal found 4/26$141

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 April 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$132
(Kiwi.com)

One-way from

$66
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$232

Good round-trip deal

$108 or less

Good one-way deal

$118 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. 13% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 28, 2026.
Use the filters below to find and compare flights from Florida to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 5/27

7:35 pm-9:25 pm

Nonstop2h 50m

Chicago Midway

Wed 6/3

4:40 pm-10:10 pm

1 stop4h 30m

$179

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Sat 5/23

7:00 am-9:10 am

Nonstop3h 10m

Chicago Midway

Tue 5/26

6:10 pm-10:05 pm

Nonstop2h 55m

$184

MiamiChicago

MIA - MDW

MIAMDW

Miami

Tue 6/9

4:00 pm-6:10 pm

Nonstop3h 10m

Chicago Midway

Tue 6/16

11:45 am-3:45 pm

Nonstop3h 00m

$199

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 7/28

9:55 pm-11:35 pm

Nonstop2h 40m

Chicago Midway

Tue 8/11

6:05 pm-9:40 pm

Nonstop2h 35m

$205

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 5/23

12:30 pm-2:20 pm

Nonstop2h 50m

Chicago Midway

Sun 5/24

4:15 pm-7:55 pm

Nonstop2h 40m

$208

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 5/29

7:20 am-9:15 am

Nonstop2h 55m

Chicago Midway

Mon 6/1

8:35 pm-12:10 am

Nonstop2h 35m

$208

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Mon 6/1

4:15 pm-9:00 pm

1 stop5h 45m

Chicago Midway

Thu 6/4

7:35 pm-11:30 pm

Nonstop2h 55m

$209

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 5/23

4:30 pm-8:05 pm

1 stop4h 35m

Chicago Midway

Mon 5/25

8:35 pm-12:10 am

Nonstop2h 35m

$209

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 5/21

5:05 pm-7:00 pm

Nonstop2h 55m

Chicago Midway

Tue 5/26

6:20 pm-9:55 pm

Nonstop2h 35m

$224

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 6/23

9:58 am-4:16 pm

1 stop7h 18m

Chicago Midway

Sat 6/27

1:21 pm-9:11 pm

1 stop6h 50m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

Showing 1-10 of 60 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Florida to Chicago Midway Airport?

The price you pay for your flight from Florida to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 84 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Florida to Chicago Midway Airport?

Currently, October is the cheapest month in which you can book a flight from Florida to Chicago Midway Airport (average of $37). Flying from Florida to Chicago Midway Airport in July is currently the most expensive (average of $95). 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 April 28, 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 12% versus a flight in the morning.

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 April 25, 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.

How much does it cost to fly round-trip from Florida to Chicago Midway Airport?

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 50m. Fly via 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 Frontier. According to our data, you can fly for as low as $45. Users have also found prices from $67 and $78 on Allegiant Air and Southwest, 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 most reliable airlines from Florida to Chicago Midway Airport?

    The top 3 most reliable airlines when flying from Florida to Chicago Midway Airport are Volaris (63%), Frontier (55%) and Southwest (53%).

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

    While on average a flight from Florida to Chicago Midway Airport is generally $245, our data shows the cheapest flight currently is $60. When looking at the most popular route, (Orlando - Chicago Midway), you can expect to pay $159 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, October is the cheapest month in which you can book a flight from Florida to Chicago Midway Airport (average of $37). Flying from Florida to Chicago Midway Airport in July is currently the most expensive (average of $95). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 April 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$166FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$278FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$149Average$340FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$202Average$350FlexibilityNo cancel feeOn-time62%

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