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C$158 Cheap Flights from Chicago Midway (MDW) to Fort Myers Southwest Florida Reg (RSW)

Compare Chicago Midway to Fort Myers Southwest Florida Reg flight deals

Find the cheapest month or even day of the year to fly to Fort Myers Southwest Florida Reg

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Flight deals from Chicago Midway to Fort Myers Southwest Florida Reg

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Fort Myers Southwest Florida Reg Airport? If you want to travel next month, return fares start from C$402. Find the lowest prices on one-way and return tickets right here.
Fort Myers.C$158 per passenger.Departing Mon., Sep. 14.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon., Sep. 14, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From C$158, select.
Fort Myers.C$195 per passenger.Departing Tue., Aug. 4.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue., Aug. 4, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From C$195, select.
Fort Myers.C$201 per passenger.Departing Wed., Aug. 26.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed., Aug. 26, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From C$201, select.
Fort Myers.C$203 per passenger.Departing Thu., Jul. 23.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu., Jul. 23, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From C$203, select.
Fort Myers.C$204 per passenger.Departing Mon., Oct. 5.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon., Oct. 5, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From C$204, select.
Fort Myers.C$217 per passenger.Departing Thu., Dec. 3.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu., Dec. 3, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From C$217, select.
Fort Myers.C$217 per passenger.Departing Tue., Nov. 10.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue., Nov. 10, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From C$217, select.
Fort Myers.C$229 per passenger.Departing Tue., Jun. 30.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue., Jun. 30, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From C$229, select.
Fort Myers.C$229 per passenger.Departing Tue., Nov. 10.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue., Nov. 10, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From C$229, select.
Fort Myers.C$310 per passenger.Departing Sun., Feb. 21.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sun., Feb. 21, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From C$310, select.
Fort Myers.C$342 per passenger.Departing Thu., Dec. 3.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu., Dec. 3, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From C$342, select.

Find the cheapest month to fly from Chicago Midway to Fort Myers Southwest Florida Reg

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Fort Myers Southwest Florida Reg flights are currently cheapest in September.
Jun.
from C$229
Jul.
from C$203
Aug.
from C$195
Sep.
from C$158
Oct.
from C$204
Nov.
from C$217
Dec.
from C$217
Jan.
Find prices
Feb.
from C$310
Mar.
Find prices
Apr.
Find prices
May
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Which airlines fly from Chicago Midway to Fort Myers Southwest Florida Reg?

Chicago Midway to Fort Myers Southwest Florida Reg: Alternative routes

Compare routes from Chicago Midway to Fort Myers below. You may find an airport to fly into that's cheaper, faster, or easier than Fort Myers Southwest Florida Reg.

Fort Myers Southwest Florida Reg

16km from central Fort Myers
Closest
from C$158
Search flights

Punta Gorda

34km from central Fort Myers
Cheapest
from C$90
Search flights

Naples

54km from central Fort Myers
Search flights

Chicago to Fort Myers: Flight information

The things to know before you go.
Cheapest flight foundC$158
Cheapest month to flySeptember
Average flight time2 hrs, 45 mins
Most popular airlineSouthwest Airlines
Average flights per week16

Finding cheap flights from Chicago Midway to Fort Myers Southwest Florida Reg: Frequently asked questions

The best price we found for a return flight from Chicago Midway to Fort Myers Southwest Florida Reg is C$317. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 45 minutes is the average flight time from Chicago Midway to Fort Myers Southwest Florida Reg.
Southwest Airlines flies direct from Chicago Midway to Fort Myers Southwest Florida Reg.
As of June 2026, there are 16 flights per week flying from Chicago Midway to Fort Myers Southwest Florida Reg.
The cheapest month to fly from Chicago Midway to Fort Myers Southwest Florida Reg is usually September.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Fort Myers Southwest Florida Reg Airport on Thursday, September 10, 2026.
Yes – the average flight time is 2 hours and 45 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Fort Myers Southwest Florida Reg but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Fort Myers is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Fort Myers Southwest Florida Reg.

Traveling from Chicago Midway International Airport (MDW) to Southwest Florida International Airport (RSW): what you need to know

  • 2 hours 46 minutes is the average length of a direct flight from Chicago Midway International Airport to Southwest Florida International Airport. Fort Myers is 1 hour ahead of Chicago and operates on the UTC-4 timezone.

  • Every week, there are 15 flights from Chicago Midway International Airport to Southwest Florida International Airport. The first flight from MDW to RSW is at 05:20 and the latest is at 21:50.

  • Traveling during a peak time like a public holiday? Expect longer queues at security and check-in. For peace of mind, arrive up to four hours before international flights and two hours before domestic departures.

  • If you'd like to break up your flight from Chicago Midway International Airport to Southwest Florida International Airport, consider adding a stopover. Just uncheck 'Direct flights only' to find a city that interests you. The most popular stopovers on the MDW - RSW route are:

    • Charlotte Douglas International Airport

    • Hartsfield-Jackson Atlanta International Airport

    • Detroit Metropolitan Wayne County Airport

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Southwest Florida International Airport (RSW)

  • The lowest price we've found for a one-way ticket from Chicago Midway International Airport to Southwest Florida International Airport is C$158. For a return flight on this route, the best price is C$316. Depending on the availability when you book, these fares may change.

  • Score cheap flight tickets from MDW to RSW by booking at least 9 months ahead. Based on our research, that's the sweet spot for landing a bargain.

  • Organize your trip for May. That's the cheapest month for flight tickets from Chicago Midway International Airport to Southwest Florida International Airport. If your travel dates are flexible, try out the 'Whole month' tool to see the lowest price across every month.

  • Getting a cheap ticket from MDW to RSW is easy with Price Alerts. All you need to do is set up one of these automatic alerts and we'll get in touch as soon as there's a better deal.

  • Use filters to tailor your flights from Chicago Midway International Airport to Southwest Florida International Airport. Simply select your ideal departure and arrival times, number of stops and airlines. Alternatively, sort your results by 'Cheapest' to see the best deals.

Handy information about Chicago Midway International Airport (MDW)

Arriving at Southwest Florida International Airport (RSW)

Getting from Southwest Florida International Airport (RSW) to central Fort Myers

  • Southwest Florida International Airport to the center of Fort Myers is around 25 minutes by car. It's approximately 23 kilometres away. Find out what options are available, such as cabs, car rentals or ride-sharing.

When to fly to Southwest Florida International Airport (RSW)

  • October is the most popular month for flights from Chicago Midway International Airport to Southwest Florida International Airport. To avoid the crowds, head to Fort Myers in May.

  • When reserving your flight from Chicago Midway International Airport to Southwest Florida International Airport, consider the kind of weather you enjoy. August is the warmest month in Fort Myers, with temperatures ranging from 25ºC to 33ºC.

  • If you want cooler conditions, search for a cheap ticket from MDW to RSW in January. Average temperatures are between 10ºC and 24ºC then.

More about Fort Myers

Complete your Fort Myers trip with hotels and a car rental

  • You've got your cheap ticket to Southwest Florida International Airport — next up is finding a great stay, and perhaps even a set of wheels. We've compared prices across hundreds of companies to bring you the top hotels and car rental deals in Fort Myers.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.