HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$50+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Florida to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 15, 2025.

Round-trip from

$92
(Cheapflightsfares)

One-way from

$50
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$148

Good round-trip deal

$95 or less

Good one-way deal

$78 or less
From Florida to Chicago Midway
Search Deals
One-way flight from Florida to Chicago Midway
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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

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 September 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 10/111:16 pmMCO - MDW
Nonstop2h 55mFrontier
Sat 10/1811:31 amMDW - MCO
Nonstop2h 40mFrontier
Deal found 9/13$92
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/48:30 amMCO - MDW
Nonstop2h 51mFrontier
Sun 10/510:13 amMDW - MCO
Nonstop2h 42mFrontier
Deal found 9/14$95
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 10/37:00 amMCO - MDW
Nonstop2h 53mFrontier
Mon 10/68:19 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 9/13$99
This Frontier deal was found by Cheapflights users on 9/15. 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 10/510:55 amTPA - MDW
Nonstop2h 49mFrontier
Mon 10/66:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 9/15$100
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 10/310:55 amTPA - MDW
Nonstop2h 49mFrontier
Sun 10/56:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 9/13$101
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 9/2610:55 amTPA - MDW
Nonstop2h 49mFrontier
Fri 10/36:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 9/14$102
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 9/267:00 amMCO - MDW
Nonstop2h 53mFrontier
Sun 9/2810:13 amMDW - MCO
Nonstop2h 42mFrontier
Deal found 9/13$102
This Frontier deal was found by Cheapflights users on 9/13. 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.
Fri 11/143:11 pmTPA - MDW
Nonstop2h 46mFrontier
Mon 11/176:06 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/13$103
This Frontier deal was found by Cheapflights users on 9/13. 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.
Fri 9/267:00 amMCO - MDW
Nonstop2h 53mFrontier
Fri 10/39:48 amMDW - MCO
Nonstop2h 40mFrontier
Deal found 9/13$103
This CheapOair deal was found by Cheapflights users on 9/14. 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.
Fri 10/242:22 pmTPA - MDW
Nonstop2h 47mFrontier
Mon 10/279:45 amMDW - TPA
Nonstop2h 37mFrontier
Deal found 9/14$104
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 9/267:00 amMCO - MDW
Nonstop2h 53mFrontier
Mon 9/298:19 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 9/13$105
This Flightnetwork deal was found by Cheapflights users on 9/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/242:26 pmMCO - MDW
Nonstop2h 54mFrontier
Mon 10/275:28 pmMDW - MCO
Nonstop2h 42mFrontier
Deal found 9/14$106

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 September 15, 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

Fri 11/14

8:14 pm-10:10 pm

Nonstop2h 56m

Chicago Midway

Mon 11/17

6:30 am-1:54 pm

1 stop6h 24m

$112

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 11/6

7:15 am-9:12 am

Nonstop2h 57m

Chicago Midway

Sat 11/8

6:30 am-1:54 pm

1 stop6h 24m

$112

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 10/11

1:16 pm-3:11 pm

Nonstop2h 55m

Chicago Midway

Tue 10/14

8:05 am-6:52 pm

1 stop9h 47m

$124

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Tue 11/4

6:50 am-8:55 am

Nonstop3h 05m

Chicago Midway

Wed 11/19

8:20 am-12:20 pm

Nonstop3h 00m

$133

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 11/4

7:15 am-9:00 am

Nonstop2h 45m

Chicago Midway

Tue 11/4

2:55 pm-6:30 pm

Nonstop2h 35m

$137

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 9/25

10:24 pm-7:11 am

1 stop9h 47m

Chicago Midway

Fri 9/26

9:48 am-1:28 pm

Nonstop2h 40m

$139

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 10/3

7:38 pm-11:41 pm

1 stop5h 03m

Chicago Midway

Fri 10/10

4:12 pm-12:42 pm

1 stop19h 30m

$143

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 10/24

7:46 pm-11:46 pm

1 stop5h 00m

Chicago Midway

Sun 10/26

6:24 pm-5:53 am

1 stop10h 29m

$143

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Fri 9/26

6:00 am-4:00 pm

1 stop11h 00m

Chicago Midway

Fri 10/3

5:15 pm-11:52 pm

1 stop5h 37m

$144

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 10/16

1:01 pm-8:21 pm

1 stop8h 20m

Chicago Midway

Sun 10/19

6:20 am-12:16 pm

1 stop4h 56m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 results
1
2
3
...
6

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 September 15, 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.

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 45m. Fly via Frontier, Southwest, or Delta to get the fastest option. There are 998 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 $55. Users have also found prices from $67 and $109 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 $264, our data shows the cheapest flight currently is $57. When looking at the most popular route, (Orlando - Chicago Midway), you can expect to pay $82 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 Chicago Midway Airport?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Florida to Midway

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Seattle to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Denver to O'Hare Intl flights
Boston to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Ontario to O'Hare Intl flights
LaGuardia to Midway flights
Newark to Midway flights
Atlanta to Midway flights
Los Angeles to Midway flights
Santa Ana to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Austin to O'Hare Intl flights
Dulles Intl to Midway flights
Baltimore to Midway flights
Hobby to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Philadelphia to Midway flights
Charlotte to O'Hare Intl flights
Minneapolis to Midway flights
Minneapolis to O'Hare Intl flights
Portland to O'Hare Intl flights
San Diego to O'Hare Intl flights
Tampa to O'Hare Intl flights
Love Field to O'Hare Intl flights
San Francisco to Midway flights
Burbank to O'Hare Intl flights
Miami to O'Hare Intl flights
Hartford to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Orlando to O'Hare Intl flights
San Jose to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Hobby to Midway flights
Love Field to Midway flights
Denver to Midway flights
Seattle to Midway flights
Providence to O'Hare Intl flights
Reagan-National to Midway flights

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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$53Average$198FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$88Average$120FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$313FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$149Average$336FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.