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Midway

$142+ Cheap flights from Fort Myers (RSW) 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — MDW
Sep 8 — Sep 151
Tue 9/8
Tue 9/15
1 adult, Economy
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Cheap flight deals from Fort Myers to Midway

Cheapest flights from Fort Myers to Midway
Explore the most affordable flight options available from Fort Myers to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 9, 2026.

This Southwest deal was found by Cheapflights users on 8/8. 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.
Sat 9/57:10 am -
Nonstop2h 45m
Sun 9/66:25 pm -
Nonstop2h 45m
Deal found 8/8$283
This Southwest deal was found by Cheapflights users on 8/6. 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.
Sat 9/57:10 am -
Nonstop2h 45m
Tue 9/158:50 am -
Nonstop2h 50m
Deal found 8/6$294
This Southwest deal was found by Cheapflights users on 8/5. 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 9/25:40 pm -
Nonstop2h 50m
Sat 9/53:05 pm -
Nonstop2h 50m
Deal found 8/5$301
This Southwest deal was found by Cheapflights users on 8/5. 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.
Mon 9/2111:55 am -
Nonstop2h 50m
Mon 9/286:15 pm -
Nonstop2h 50m
Deal found 8/5$305
This Southwest deal was found by Cheapflights users on 8/6. 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 9/35:25 pm -
Nonstop2h 50m
Thu 9/106:15 pm -
Nonstop2h 50m
Deal found 8/6$312

Find flight deals from Fort Myers to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Fort Myers (RSW) 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 August 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$278
(Southwest)

One-way from

$142
(Southwest)

Popular in

March

Cheapest in

October

Average price

$309
Provider with most accurate pricing for Fort Myers SW Florida Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-Chicago Midway flights.
Search Deals
From Fort Myers SW Florida Intl to Chicago Midway
Search Deals
One-way flight from Fort Myers SW Florida Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Fort Myers 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 August 9, 2026.
Use the filters below to find and compare flights from Fort Myers to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Sat 9/5

6:25 am-1:05 pm

2 stops7h 40m

Chicago Midway

Sun 9/6

8:50 am-6:30 pm

1 stop8h 40m

$314

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 9/11

5:25 pm-7:15 pm

Nonstop2h 50m

Chicago Midway

Fri 9/18

10:30 am-5:45 pm

1 stop6h 15m

$323

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Sat 11/7

7:05 am-1:25 pm

2 stops7h 20m

Chicago Midway

Mon 11/9

5:10 am-11:45 am

1 stop5h 35m

$330

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Sat 9/5

6:25 am-1:05 pm

2 stops7h 40m

Chicago Midway

Tue 9/8

1:00 pm-7:55 pm

2 stops5h 55m

$335
Quickest round-trip

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Sat 10/10

7:30 am-9:20 am

Nonstop2h 50m

Chicago Midway

Sun 10/11

7:00 pm-10:45 pm

Nonstop2h 45m

$336

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Thu 9/17

5:25 pm-7:15 pm

Nonstop2h 50m

Chicago Midway

Sun 9/20

9:00 am-12:45 pm

Nonstop2h 45m

$336

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 9/11

3:40 pm-10:00 pm

2 stops7h 20m

Chicago Midway

Sun 9/20

5:00 am-11:15 am

1 stop5h 15m

$350

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Wed 8/26

5:35 am-11:51 am

1 stop7h 16m

Chicago Midway

Fri 8/28

12:46 pm-6:58 pm

1 stop5h 12m

$351

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Fri 9/25

6:50 am-8:40 am

Nonstop2h 50m

Chicago Midway

Sun 9/27

9:00 am-12:45 pm

Nonstop2h 45m

$356
Cheapest one-way
Quickest one-way

Fort MyersChicago

RSW Fort Myers SW Florida Intl - MDW Chicago Midway

RSWMDW

Fort Myers SW Florida Intl

Sat 10/3

4:15 pm-6:05 pm

Nonstop2h 50m

$153

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Compare providers for flights from Fort Myers to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Fort Myers to Midway in August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Fort Myers-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Fort Myers-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Fort Myers-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Fort Myers-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Fort Myers-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Fort Myers to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Fort Myers 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 Fort Myers to Chicago Midway Airport

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

Currently, October is the cheapest month in which you can book a flight from Fort Myers to Chicago Midway Airport (average of $255). Flying from Fort Myers to Chicago Midway Airport in March is currently the most expensive (average of $504). 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 RSW to MDW?

Find hourly flight availability from Fort Myers 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 August 9, 2026.

One of the essential ways to save on airfare from Fort Myers to Chicago Midway Airport is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 36% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Fort Myers to Midway. Price data was last updated on August 1, 2026.

Travelers seeking maximum savings on their Fort Myers to Chicago Midway Airport flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday evenings 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 Fort Myers to Chicago Midway Airport?

Airfare is below average for this route at the moment.

Fort Myers to Chicago Midway Airport flights typically cost between $283 and $374 in September.
The cheapest round-trip price found within the last 5 days was $278 on Southwest (Sep 5-Sep 6).

The best insider tips for Fort Myers to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Fort Myers to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Matt Meltzer

Matt Meltzer

Expert on RSW

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more

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 August 9, 2026.
Get a feel of what it's like to fly with Southwest from Fort Myers to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,216 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,216 reviews
Southwest
8.0
Very good
4,216 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

Find useful and relevant information for your journey from Fort Myers to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Fort Myers to Chicago Midway?

    If you book a flight to Chicago Midway from Fort Myers, you will be flying from SW Florida Intl, which is the city’s only airport. Fort Myers SW Florida Intl (RSW) is located 10.0 mi from the center of Fort Myers. There is 1 flight from SW Florida Intl to Chicago Midway per day from 1 airline.

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

    Airlines like Southwest fly from Fort Myers to Chicago Midway Airport in about 7h 40m. The time it takes to get you to your destination can typically vary by up to . The distance between Fort Myers and Chicago Midway Airport is about 1106 mi.

  • What is the cheapest airline to fly from Fort Myers to Chicago Midway Airport round-trip?

    Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $183. You may be able to fly from Fort Myers to Chicago Midway Airport for 50% less than the average price by searching for this airline.

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

    On average you can expect to pay $362 for a flight from Fort Myers to Chicago Midway Airport. The cheapest flight overall is $182 while the most popular route, (Fort Myers SW Florida Intl - Chicago Midway) is currently priced at $299.

  • Can I find deals for flights from Fort Myers to Midway that include hotel bookings?

    Yes. In addition to deals on Fort Myers to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Fort Myers to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Fort Myers to Midway.

  • Can I find deals for business class flights from Fort Myers to Midway?

    Yes. Cheapflights offers flight deals from Fort Myers 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 Fort Myers to Chicago Midway Airport?

    Currently, October is the cheapest month in which you can book a flight from Fort Myers to Chicago Midway Airport (average of $255). Flying from Fort Myers to Chicago Midway Airport in March is currently the most expensive (average of $504). 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
Valparaiso
Hammond
Saint Joseph
Porter

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Top airline flying from Fort Myers to Midway

Discover the top airline that operate flights from Fort Myers 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 August 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$183Average$356FlexibilityNo cancel feeOn-time63%

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