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Midway

$145+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — MDW
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
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 May 10, 2026.

This Southwest deal was found by Cheapflights users on 5/8. 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.
Tue 6/27:00 am
RSW
-
MDW
Nonstop2h 55m
Southwest
Wed 6/34:05 pm
MDW
-
RSW
Nonstop2h 45m
Southwest
Deal found 5/8$291
This Southwest deal was found by Cheapflights users on 5/7. 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 6/185:10 am
RSW
-
MDW
Nonstop2h 50m
Southwest
Tue 6/236:55 pm
MDW
-
RSW
Nonstop2h 45m
Southwest
Deal found 5/7$293
This Southwest deal was found by Cheapflights users on 5/8. 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.
Thu 6/115:10 am
RSW
-
MDW
Nonstop2h 50m
Southwest
Mon 6/156:55 pm
MDW
-
RSW
Nonstop2h 45m
Southwest
Deal found 5/8$295
This Southwest deal was found by Cheapflights users on 5/7. 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 6/67:50 pm
RSW
-
MDW
1 stop4h 25m
Southwest
Tue 6/96:55 pm
MDW
-
RSW
Nonstop2h 45m
Southwest
Deal found 5/7$303
This Southwest deal was found by Cheapflights users on 5/7. 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 6/255:10 pm
RSW
-
MDW
Nonstop2h 55m
Southwest
Mon 6/291:00 pm
MDW
-
RSW
2 stops7h 55m
Southwest
Deal found 5/7$310
This Delta deal was found by Cheapflights users on 5/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/165:37 am
RSW
-
MDW
1 stop7h 28m
Delta
Tue 6/306:00 am
MDW
-
RSW
1 stop7h 33m
Delta
Deal found 5/6$311
This Southwest deal was found by Cheapflights users on 5/7. 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 5/306:00 am
RSW
-
MDW
Nonstop2h 55m
Southwest
Tue 6/24:05 pm
MDW
-
RSW
Nonstop2h 45m
Southwest
Deal found 5/7$312
This Southwest deal was found by Cheapflights users on 5/7. 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 6/166:00 am
RSW
-
MDW
1 stop7h 25m
Southwest
Sat 6/205:00 am
MDW
-
RSW
1 stop7h 15m
Southwest
Deal found 5/7$313

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 May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$291
(Southwest)

One-way from

$145
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$319
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. 9% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 10, 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 - MDW

RSWMDW

Fort Myers SW Florida Intl

Tue 6/2

7:00 am-8:55 am

Nonstop2h 55m

Chicago Midway

Wed 6/3

4:05 pm-7:50 pm

Nonstop2h 45m

$291

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 6/18

5:10 am-7:00 am

Nonstop2h 50m

Chicago Midway

Tue 6/23

5:10 pm-10:35 pm

1 stop4h 25m

$303

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Tue 7/21

11:25 am-5:05 pm

1 stop6h 40m

Chicago Midway

Sat 7/25

5:55 pm-9:40 pm

Nonstop2h 45m

$303

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Wed 7/22

6:45 am-11:56 am

1 stop6h 11m

Chicago Midway

Wed 8/5

10:54 am-4:44 pm

1 stop4h 50m

$311

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 5/30

6:00 am-7:55 am

Nonstop2h 55m

Chicago Midway

Wed 6/3

4:05 pm-7:50 pm

Nonstop2h 45m

$312
Quickest round-trip

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 7/30

5:10 am-7:00 am

Nonstop2h 50m

Chicago Midway

Tue 8/4

6:00 pm-9:45 pm

Nonstop2h 45m

$315

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 9/12

7:20 am-1:10 pm

2 stops6h 50m

Chicago Midway

Tue 9/15

6:15 am-11:35 am

1 stop4h 20m

$318

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 6/6

9:25 am-5:00 pm

2 stops8h 35m

Chicago Midway

Tue 6/9

2:35 pm-10:35 pm

1 stop7h 00m

$318

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 9/5

3:20 pm-5:10 pm

Nonstop2h 50m

Chicago Midway

Tue 9/8

1:55 pm-10:10 pm

1 stop7h 15m

$322

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 5/30

6:00 am-7:55 am

Nonstop2h 55m

Chicago Midway

Tue 6/2

10:10 am-5:10 pm

2 stops6h 00m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 18 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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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, August is the cheapest month in which you can book a flight from Fort Myers to Chicago Midway Airport (average of $208). Flying from Fort Myers to Chicago Midway Airport in March is currently the most expensive (average of $500). 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 May 10, 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 in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 28% 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 May 9, 2026.

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

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 May 10, 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
4,304 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,304 reviews
Southwest
8.0
Very good
4,304 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 are 2 flights 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 and Delta fly from Fort Myers to Chicago Midway Airport in about 2h 55m. The time it takes to get you to your destination can typically vary by up to 3h 16m. The distance between Fort Myers and Chicago Midway Airport is about 1106 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $159. You may be able to fly from Fort Myers to Chicago Midway Airport for 54% 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 $335 for a flight from Fort Myers to Chicago Midway Airport. The cheapest flight overall is $166 while the most popular route, (Fort Myers SW Florida Intl - Chicago Midway) is currently priced at $291.

  • 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, August is the cheapest month in which you can book a flight from Fort Myers to Chicago Midway Airport (average of $208). Flying from Fort Myers to Chicago Midway Airport in March is currently the most expensive (average of $500). 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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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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$159Average$357FlexibilityNo cancel feeOn-time63%

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