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$142+ Cheap flights from Midway (MDW) to Fort Myers (RSW)

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.
MDW — RSW
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Fort Myers SW Florida Intl are usually found in January or October, booked 61 days in advance, depart on a Monday or Wednesday and return on a Thursday

Cheap flight deals from Midway to Fort Myers

Cheapest flights from Midway to Fort Myers
Explore the most affordable flight options available from Midway to Fort Myers. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 27, 2026.

This Southwest deal was found by Cheapflights users on 7/22. 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 8/198:50 am
MDW
-
RSW
Nonstop2h 50m
Southwest
Sat 8/297:10 am
RSW
-
MDW
Nonstop2h 45m
Southwest
Deal found 7/22$275
This Southwest deal was found by Cheapflights users on 7/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:50 am
MDW
-
RSW
Nonstop2h 50m
Southwest
Wed 8/195:40 pm
RSW
-
MDW
Nonstop2h 50m
Southwest
Deal found 7/24$283
This Southwest deal was found by Cheapflights users on 7/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:15 pm
MDW
-
RSW
Nonstop2h 50m
Southwest
Tue 9/157:10 am
RSW
-
MDW
Nonstop2h 45m
Southwest
Deal found 7/25$284
This Southwest deal was found by Cheapflights users on 7/22. 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 8/192:40 pm
MDW
-
RSW
1 stop4h 10m
Southwest
Mon 8/2411:55 am
RSW
-
MDW
Nonstop2h 50m
Southwest
Deal found 7/22$285
This Southwest deal was found by Cheapflights users on 7/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:40 pm
MDW
-
RSW
Nonstop2h 45m
Southwest
Thu 11/510:50 am
RSW
-
MDW
1 stop4h 20m
Southwest
Deal found 7/24$289
This Southwest deal was found by Cheapflights users on 7/22. 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 8/191:00 pm
MDW
-
RSW
2 stops5h 50m
Southwest
Tue 8/255:40 pm
RSW
-
MDW
Nonstop2h 50m
Southwest
Deal found 7/22$290
This Southwest deal was found by Cheapflights users on 7/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:00 am
MDW
-
RSW
Nonstop2h 45m
Southwest
Thu 8/205:25 pm
RSW
-
MDW
Nonstop2h 50m
Southwest
Deal found 7/23$292
This Southwest deal was found by Cheapflights users on 7/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:00 pm
MDW
-
RSW
Nonstop2h 45m
Southwest
Mon 9/76:50 am
RSW
-
MDW
Nonstop2h 50m
Southwest
Deal found 7/26$294
This Delta deal was found by Cheapflights users on 7/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:05 am
MDW
-
RSW
1 stop5h 08m
Delta
Wed 8/266:29 pm
RSW
-
MDW
1 stop5h 07m
Delta
Deal found 7/23$295
This Southwest deal was found by Cheapflights users on 7/22. 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 8/198:50 am
MDW
-
RSW
1 stop6h 20m
Southwest
Wed 8/267:20 am
RSW
-
MDW
2 stops9h 30m
Southwest
Deal found 7/22$300

Find flight deals from Midway to Fort Myers

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Fort Myers (RSW). 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 July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$275
(Southwest)

One-way from

$142
(Southwest)

Popular in

March

Cheapest in

January

Average price

$416
Provider with most accurate pricing for Chicago Midway-Fort Myers SW Florida Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Fort Myers SW Florida Intl flights.
Search Deals
From Chicago Midway to Fort Myers SW Florida Intl
Search Deals
One-way flight from Chicago Midway to Fort Myers SW Florida Intl
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($67 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 July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Fort Myers 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 July 27, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Fort Myers that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 8/19

6:00 pm-9:45 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Mon 8/24

11:55 am-1:45 pm

Nonstop2h 50m

$283

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 9/26

7:45 am-3:40 pm

1 stop6h 55m

Fort Myers SW Florida Intl

Sat 10/3

7:30 am-9:20 am

Nonstop2h 50m

$285

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 9/5

3:05 pm-6:50 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Tue 9/8

12:20 pm-7:05 pm

2 stops7h 45m

$290

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 11/7

3:35 pm-7:20 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Tue 11/10

12:00 pm-3:35 pm

1 stop4h 35m

$293

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 8/19

5:10 pm-12:40 am

1 stop6h 30m

Fort Myers SW Florida Intl

Mon 8/24

6:29 pm-10:36 pm

1 stop5h 07m

$303

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 8/18

8:50 am-4:10 pm

1 stop6h 20m

Fort Myers SW Florida Intl

Sat 8/22

7:20 am-12:30 pm

2 stops6h 10m

$308

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Mon 8/17

7:55 am-3:05 pm

2 stops6h 10m

Fort Myers SW Florida Intl

Sat 8/22

7:20 am-12:30 pm

2 stops6h 10m

$331
Cheapest one-way

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 9/26

3:05 pm-6:55 pm

Nonstop2h 50m

$142
Quickest one-way

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Thu 9/3

9:00 am-12:45 pm

Nonstop2h 45m

$142

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Mon 10/26

5:15 pm-11:10 pm

1 stop4h 55m

$152

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

Compare providers for flights from Midway to Fort Myers

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 Midway to Fort Myers in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapTicketsDealPrice 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 Chicago Midway Airport-Fort Myers flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Fort Myers flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Fort Myers flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Fort Myers 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 Chicago Midway Airport-Fort Myers 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 Midway to Fort Myers

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

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

The best time to book flights from Chicago Midway Airport to Fort Myers is 60 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Fort Myers (average of $264). Flying from Chicago Midway Airport to Fort Myers in March is currently the most expensive (average of $520). 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 MDW to RSW?

Find hourly flight availability from Midway to Fort Myers. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 27, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 22% on flights from Chicago Midway Airport to Fort Myers by exploring options for tickets in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Midway to Fort Myers. Price data was last updated on July 18, 2026.

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

Airfare is below average for this route at the moment.

Chicago Midway Airport to Fort Myers flights typically cost between $315 and $342 in August.
The cheapest round-trip price found within the last 5 days was $275 on Southwest (Aug 19-Aug 29).

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

Get insights into the airlines that provide service to Fort Myers. 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 Fort Myers. Reviews last updated July 27, 2026.
Read reviews from past customers who have flown Southwest and Delta from Chicago Midway Airport to Fort Myers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,228 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,228 reviews
Southwest
8.0
Very good
4,228 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
7.8
Good
8,483 reviews
Southwest
8.0
Very good
4,228 reviews

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Midway to Fort Myers. 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 into for flights to Fort Myers from Chicago Midway?

    If you book a flight to Fort Myers from Chicago Midway, you will be flying to 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 Chicago Midway to SW Florida Intl per day from 2 different airlines.

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

    There are many flights that can get you from Chicago Midway Airport to Fort Myers in 2h 45m. Fly via Southwest to get the fastest option. The distance from Chicago Midway Airport to Fort Myers is about 1106 mi. All flights are typically nonstop.

  • What are the cheapest airlines flying from Chicago Midway Airport to Fort Myers round-trip?

    Flying on Southwest is currently your cheapest option to Fort Myers, with prices starting at $237. Another option worth looking into is Delta, starting at $287 round trip. Southwest is priced at 38% lower than the current average price of a flight leaving 3 months from now.

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

    Looking at all options, your cheapest flight can be booked for $95. While the most popular route (Chicago Midway - Fort Myers SW Florida Intl) can be booked for $283 on average, our data indicates $331 when flying from Chicago Midway Airport to Fort Myers.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Fort Myers (average of $264). Flying from Chicago Midway Airport to Fort Myers in March is currently the most expensive (average of $520). 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 Fort Myers?

Book flights to Fort Myers if you plan to visit one of these locations
North Fort Myers
Sanibel
Lehigh Acres

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Midway to Fort Myers

Discover the top 2 airlines that operate flights from Midway to Fort Myers. 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 July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$237Average$386FlexibilityNo cancel feeOn-time63%
DeltaCheapest$287Average$355FlexibilityNo cancel feeOn-timeN/A

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