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$67+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RSW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September or January, booked 30 days in advance, depart on a Monday or Wednesday and return on a Wednesday

Cheap 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 September 11, 2025.

Round-trip from

$133
(Southwest)

One-way from

$67
(Southwest)

Popular in

December

Cheapest in

September

Average price

$230
From Chicago Midway to Fort Myers SW Florida Intl
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One-way flight from Chicago Midway to Fort Myers SW Florida Intl
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Highest demand for flights based on searches. 7% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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 10/286:50 pmMDW - RSW
Nonstop2h 40mSouthwest
Tue 11/46:30 amRSW - MDW
Nonstop2h 55mSouthwest
Deal found 9/11$133
This Frontier deal was found by Cheapflights users on 9/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/39:15 amMDW - RSW
1 stop10h 18mFrontier
Sun 11/91:13 pmRSW - MDW
1 stop9h 50mFrontier
Deal found 9/8$144
This Booking.com deal was found by Cheapflights users on 9/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/266:20 amMDW - RSW
1 stop4h 56mFrontier
Sat 11/19:28 pmRSW - MDW
1 stop12h 02mFrontier
Deal found 9/11$145
This Southwest deal was found by Cheapflights users on 9/11. 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.
Sun 10/268:30 pmMDW - RSW
Nonstop2h 40mSouthwest
Sat 11/17:10 amRSW - MDW
Nonstop2h 50mSouthwest
Deal found 9/11$146
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:15 amMDW - RSW
1 stop4h 57mFrontier
Thu 11/131:13 pmRSW - MDW
1 stop6h 26mFrontier
Deal found 9/8$152
This Frontier deal was found by Cheapflights users on 9/10. 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 10/126:20 amMDW - RSW
1 stop4h 56mFrontier
Thu 10/161:01 pmRSW - MDW
1 stop11h 45mFrontier
Deal found 9/10$153
This Frontier deal was found by Cheapflights users on 9/11. 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.
Thu 9/186:20 amMDW - RSW
1 stop11h 09mFrontier
Thu 10/161:01 pmRSW - MDW
1 stop8h 20mFrontier
Deal found 9/11$154
This Southwest deal was found by Cheapflights users on 9/10. 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 10/87:50 amMDW - RSW
Nonstop2h 40mSouthwest
Wed 10/156:05 amRSW - MDW
Nonstop2h 50mSouthwest
Deal found 9/10$156
This Southwest deal was found by Cheapflights users on 9/10. 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.
Sun 12/75:35 amMDW - RSW
Nonstop2h 45mSouthwest
Sun 12/148:50 pmRSW - MDW
Nonstop2h 55mSouthwest
Deal found 9/10$162
This Frontier deal was found by Cheapflights users on 9/10. 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.
Thu 11/139:15 amMDW - RSW
1 stop10h 18mFrontier
Sun 11/161:13 pmRSW - MDW
1 stop9h 50mFrontier
Deal found 9/10$163
This Frontier deal was found by Cheapflights users on 9/11. 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 10/266:20 amMDW - RSW
1 stop4h 56mFrontier
Sun 11/21:13 pmRSW - MDW
1 stop9h 50mFrontier
Deal found 9/11$164

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 September 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Fort Myers that are best for you.

Fly from

Midway

Fly to

Fort Myers

Route

Depart

Return

Price

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 1/13

5:45 pm-9:30 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Fri 1/23

7:25 am-9:20 am

Nonstop2h 55m

$165

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 10/18

5:30 pm-9:10 pm

Nonstop2h 40m

Fort Myers SW Florida Intl

Wed 10/22

6:05 am-7:55 am

Nonstop2h 50m

$175

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 10/15

6:50 pm-10:30 pm

Nonstop2h 40m

Fort Myers SW Florida Intl

Wed 10/22

6:05 am-7:55 am

Nonstop2h 50m

$186

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 10/8

5:45 am-12:00 pm

1 stop5h 15m

Fort Myers SW Florida Intl

Sat 10/11

7:10 am-9:00 am

Nonstop2h 50m

$187

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 11/5

5:35 am-10:55 am

1 stop4h 20m

Fort Myers SW Florida Intl

Wed 11/12

6:30 am-8:25 am

Nonstop2h 55m

$203

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 10/18

5:30 pm-9:10 pm

Nonstop2h 40m

Fort Myers SW Florida Intl

Sat 10/25

4:20 pm-10:35 pm

1 stop7h 15m

$205

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 11/12

5:35 am-10:55 am

1 stop4h 20m

Fort Myers SW Florida Intl

Tue 11/18

4:40 pm-8:15 pm

1 stop4h 35m

$206

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 12/10

6:15 pm-10:10 pm

Nonstop2h 55m

Fort Myers SW Florida Intl

Sat 12/13

7:50 am-9:45 am

Nonstop2h 55m

$208

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Fri 12/5

1:14 pm-9:46 pm

1 stop7h 32m

Fort Myers SW Florida Intl

Mon 12/8

5:38 pm-11:32 pm

1 stop6h 54m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sun 1/11

6:00 am-12:03 pm

1 stop5h 03m

Fort Myers SW Florida Intl

Fri 1/16

5:40 pm-9:46 pm

1 stop5h 06m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 22 results
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The best insider tips for Chicago Midway Airport to Fort Myers flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Fort Myers trip
Airports
MDW

Use the Orange Line train to reach MDW easily and affordably. It connects directly to the airport and operates almost 24 hours a day.

Read more about MDWby Ramsey Qubein
RSW

At RSW, baggage claim is quick and efficient. Bags usually arrive within 15 minutes, even during busy periods like spring break.

Read more about RSWby Matt Meltzer
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

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

Matt Meltzer

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

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?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Fort Myers. Price data was last updated on August 29, 2025.

The best time to book flights from Chicago Midway Airport to Fort Myers is 30 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 $205). Flying from Chicago Midway Airport to Fort Myers in June is currently the most expensive (average of $290). 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 September 11, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 16% 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 September 7, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Fort Myers flight should consider departing on Monday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 September 11, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Spirit Airlines 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
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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.
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

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 3 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 Spirit Airlines is currently your cheapest option to Fort Myers, with prices starting at $114. Additional round-trip tickets that might be worth considering are offered by Southwest and Delta, with the lowest prices starting at $174 and $216, respectively. Spirit Airlines is priced at 68% 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 $91. While the most popular route (Chicago Midway - Fort Myers SW Florida Intl) can be booked for $146 on average, our data indicates $238 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 $205). Flying from Chicago Midway Airport to Fort Myers in June is currently the most expensive (average of $290). 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
Sanibel
North Fort Myers
Estero
Lehigh Acres

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Alternative routes for Midway to Fort Myers

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Midway to Fort Myers

Discover the top 3 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$114Average$364FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$174Average$384FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$357FlexibilityNo cancel feeOn-timeN/A

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