$66 Cheap Flights from Chicago (MDW) to Fort Myers (RSW)

View $66 flight on Sat, Oct 25, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Southwest Florida Intl. Airport (RSW)

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Cheap Flights from Chicago to Fort Myers (MDW-RSW)

Prices were available within the past 7 days and start at $66 for one-way flights and $132 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Oct 18 - Sat, Nov 1
MDW
Chicago
RSW
Fort Myers
$132 Roundtrip, found 5 hours ago
$132
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, Oct 18 from Chicago to Fort Myers, returning Sat, Nov 1, priced at $132 found 5 hours ago
Southwest Airlines
Tue, Aug 12 - Fri, Aug 15
MDW
Chicago
RSW
Fort Myers
$134 Roundtrip, just found
$134
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Aug 12 from Chicago to Fort Myers, returning Fri, Aug 15, priced at $134 just found
Southwest Airlines
Fri, Sep 5 - Tue, Sep 9
MDW
Chicago
RSW
Fort Myers
$143 Roundtrip, found 5 hours ago
$143
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Fri, Sep 5 from Chicago to Fort Myers, returning Tue, Sep 9, priced at $143 found 5 hours ago
Southwest Airlines
Mon, Oct 20 - Mon, Nov 3
MDW
Chicago
RSW
Fort Myers
$143 Roundtrip, found 5 hours ago
$143
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Mon, Oct 20 from Chicago to Fort Myers, returning Mon, Nov 3, priced at $143 found 5 hours ago
Southwest Airlines
Sat, Oct 11 - Tue, Oct 14
MDW
Chicago
RSW
Fort Myers
$145 Roundtrip, found 4 hours ago
$145
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Oct 11 from Chicago to Fort Myers, returning Tue, Oct 14, priced at $145 found 4 hours ago
Southwest Airlines
Tue, Aug 12 - Fri, Aug 15
MDW
Chicago
RSW
Fort Myers
$146 Roundtrip, just found
$146
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Aug 12 from Chicago to Fort Myers, returning Fri, Aug 15, priced at $146 just found
Southwest Airlines
Tue, Aug 12 - Fri, Aug 15
MDW
Chicago
RSW
Fort Myers
$147 Roundtrip, just found
$147
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Aug 12 from Chicago to Fort Myers, returning Fri, Aug 15, priced at $147 just found
Southwest Airlines
Wed, Aug 13 - Fri, Aug 15
MDW
Chicago
RSW
Fort Myers
$148 Roundtrip, found 3 hours ago
$148
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, Aug 13 from Chicago to Fort Myers, returning Fri, Aug 15, priced at $148 found 3 hours ago
Southwest Airlines
Tue, Sep 23 - Fri, Sep 26
MDW
Chicago
RSW
Fort Myers
$150 Roundtrip, found 5 hours ago
$150
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Tue, Sep 23 from Chicago to Fort Myers, returning Fri, Sep 26, priced at $150 found 5 hours ago
Southwest Airlines
Sun, Aug 17 - Sat, Aug 23
MDW
Chicago
RSW
Fort Myers
$152 Roundtrip, found 2 hours ago
$152
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sun, Aug 17 from Chicago to Fort Myers, returning Sat, Aug 23, priced at $152 found 2 hours ago

Find the cheapest month to fly from Chicago (MDW) to Fort Myers (RSW)

September is typically the cheapest month to fly

From $138 - $520 per traveler.

Graph displaying average flight prices per month

Alternative airports near Fort Myers

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Southwest Florida Intl. RSW. Cheapest option available. Average driving time to city center is 22 minutes. Flights from $229
RSW
Southwest Florida Intl.
Cheapest
Average driving time to city center22 min
Flights from $229
Flights from Chicago (MDW) to Fort Myers (RSW)
Origin airport
Midway Intl.
Destination airport
Southwest Florida Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$132
Distance
1107 mi
Average flight time
3 hours 43 mins

Chicago to Fort Myers Flights

The cheapest times to fly from Chicago to Fort Myers

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Fort Myers are during the month of October. You can find some of the cheapest flights from Chicago to Fort Myers with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Fort Myers

Sunday is one of the best days to book for cheap flights from Chicago to Fort Myers: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Fort Myers

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Fort Myers in 2025. You can also book with separate airlines for your outbound and return journeys, from $66 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Fort Myers flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Fort Myers airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Southwest Florida Intl. Airport (RSW) cost?
Cheap round-trip flights from Midway Intl. Airport (MDW) to Southwest Florida Intl. Airport (RSW) start at $124. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and Spirit Airlines flight leaving MDW on August 2 2025 and touching down at RSW. The price was last updated on July 6 2025 and has not changed since.
What is the cheapest month to fly from MDW to RSW?
The cheapest flights from MDW to RSW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Southwest Florida Intl. Airport (RSW)?
When heading out of Midway Intl. Airport (MDW), you can board a nonstop flight to Southwest Florida Intl. Airport (RSW) with Southwest Airlines.
What is the cheapest airline that flies from MDW to RSW?
With tickets starting at $79 for a one-way journey from MDW to RSW, Southwest Airlines is currently the cheapest carrier operating this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on September 20 2025. Prices were last updated on July 6 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Southwest Florida Intl. Airport (RSW)?
With an average of 3 direct flights that operate from Midway Intl. Airport (MDW) to Southwest Florida Intl. Airport (RSW) daily, you'll be up in the air in no time.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Southwest Florida Intl. Airport (RSW)?
The 1 PM departures from MDW to RSW are typically the busiest. These flights can come with a higher price due to their popularity. If you're hoping to save money, book during off-peak hours.
What day of the week has the most flights from MDW to RSW?
Friday has the most flights from Midway Intl. Airport (MDW) to Southwest Florida Intl. Airport (RSW). Consider leaving on this day and you'll have the best chance of finding a departure that fits your schedule.
What is the earliest flight from Midway Intl. Airport (MDW) to Southwest Florida Intl. Airport (RSW)?
The first flight of the day taking off from Midway Intl. Airport (MDW) is at around 6:05AM UTC-6. Board this plane and you'll land at Southwest Florida Intl. Airport (RSW) at approximately 10:05AM UTC-5. The overall travel time is 3h.
How long does it take to fly from Midway Intl. Airport (MDW) to Southwest Florida Intl. Airport (RSW)?
The average flight time from MDW to RSW is 2 hours and 52 minutes, covering a total distance of 1,100 mi.
What is the best time to fly from Midway Intl. Airport (MDW) to Southwest Florida Intl. Airport (RSW)?
To avoid potential delays on the Midway Intl. Airport (MDW) to Southwest Florida Intl. Airport (RSW) route, aim to travel before 3 PM. Later flights are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Fort Myers from Midway Intl. Airport (MDW)?
Hop on a direct flight from Midway Intl. Airport (MDW) to Fort Myers and arrive at Southwest Florida Intl. Airport (RSW). Another gateway to this destination is Charlotte County Airport (PGD).
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Southwest Florida Intl. Airport (RSW) last-minute?
Last-minute bookings from MDW to RSW are generally more expensive. For the cheapest rates, start looking for flights ahead of time. That being said, if you can play around with your travel dates, you may find a cheap fare right before your trip.
Is it cheaper to book a MDW to RSW flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to RSW flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one place will take the hassle out of planning your trip. Just secure your flights and choose from our extensive range of stays, then customize your trip with extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Southwest Florida Intl. Airport (RSW)?
Generally, it's possible to reschedule or cancel your MDW to RSW flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more details on our Customer Service portal.

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