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$79+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RSW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 Friday

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 June 12, 2025.

Round-trip from

$158
(Southwest)

One-way from

$79
(Southwest)

Popular in

December

Cheapest in

September

Average price

$429
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. 8% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/11. 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.
Wed 10/87:50 amMDW - RSW
Nonstop2h 40mSouthwest
Wed 10/154:20 pmRSW - MDW
Nonstop2h 50mSouthwest
Deal found 6/11$157
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2912:43 pmMDW - RSW
1 stop6h 51mDelta
Wed 7/305:40 amRSW - MDW
1 stop5h 05mDelta
Deal found 6/11$217
This Frontier deal was found by Cheapflights users on 6/12. 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 8/76:20 amMDW - RSW
1 stop11h 00mFrontier
Sun 8/107:16 pmRSW - MDW
1 stop5h 01mFrontier
Deal found 6/12$234

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 June 12, 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

Sun 8/24

6:55 pm-10:40 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Sat 8/30

4:25 pm-6:15 pm

Nonstop2h 50m

$158

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Fri 7/11

6:47 pm-12:45 am

1 stop4h 58m

Fort Myers SW Florida Intl

Tue 7/22

5:40 am-9:45 am

1 stop5h 05m

$227

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Thu 8/7

6:20 am-6:20 pm

1 stop11h 00m

Fort Myers SW Florida Intl

Sun 8/10

7:16 pm-11:17 pm

1 stop5h 01m

$234

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 8/13

6:20 pm-10:05 pm

Nonstop2h 45m

$79

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Thu 8/21

11:03 am-6:24 pm

1 stop6h 21m

$112

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 7/15

10:30 am-6:41 pm

1 stop7h 11m

$119

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Thu 8/28

11:03 am-10:36 am

3 stops46h 33m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 9, 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 $297). 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 June 12, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 19% 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 June 8, 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.

Rainfall in Fort Myers by month

Plan your trip to Fort Myers by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Fort Myers ranges from 1.7 - 10.1 inches per month. June is typically the wettest month, when rainfall can reach 10.1 in. December is typically the driest time to visit Fort Myers when rainfall is around 1.7 in.

Temperature in Fort Myers by month

Plan your trip to Fort Myers by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Fort Myers, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).

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 June 12, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Frontier from Chicago to Fort Myers to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

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
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

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.
Frontier
5.9
Fair
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

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 4 different airlines.

  • 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 $158. Additional round-trip tickets that might be worth considering are offered by Delta and Frontier, with the lowest prices starting at $227 and $234, respectively. Southwest is priced at 56% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Fort Myers one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $79. Users have also found prices from $112 and $119 on Frontier and Delta, respectively.

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

    Looking at all options, your cheapest flight can be booked for $98. While the most popular route (Chicago Midway - Fort Myers SW Florida Intl) can be booked for $157 on average our data indicates $269 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 $297). 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
North Fort Myers
Sanibel
Estero
Lehigh Acres

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Top 4 airlines flying from Midway to Fort Myers

Discover the top 4 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$95Average$365FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$114Average$364FlexibilityNo cancel feeOn-time65%
DeltaCheapest$216Average$357FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$235Average$388FlexibilityNo cancel feeOn-time63%

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