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C$130 Cheap Flights from Fort Myers Southwest Florida Reg (RSW) to Chicago Midway (MDW)

Compare Fort Myers Southwest Florida Reg to Chicago Midway flight deals

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Flight deals from Fort Myers Southwest Florida Reg to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Fort Myers Southwest Florida Reg Airport to Chicago Midway Airport? If you want to travel next month, return fares start from C$406. Find the lowest prices on one-way and return tickets right here.
Chicago.C$130 per passenger.Departing Wed., Sep. 16.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Wed., Sep. 16, arriving in Chicago Midway.Price includes taxes and charges.From C$130, select.
Chicago.C$203 per passenger.Departing Sat., Aug. 15.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Sat., Aug. 15, arriving in Chicago Midway.Price includes taxes and charges.From C$203, select.
Chicago.C$204 per passenger.Departing Sat., Oct. 3.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Sat., Oct. 3, arriving in Chicago Midway.Price includes taxes and charges.From C$204, select.
Chicago.C$204 per passenger.Departing Wed., Jul. 22.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Wed., Jul. 22, arriving in Chicago Midway.Price includes taxes and charges.From C$204, select.
Chicago.C$218 per passenger.Departing Wed., Dec. 2.One-way flight with Delta.Outbound indirect flight with Delta, departs from Fort Myers Southwest Florida Reg on Wed., Dec. 2, arriving in Chicago Midway.Price includes taxes and charges.From C$218, select.
Chicago.C$218 per passenger.Departing Thu., Nov. 26.One-way flight with Delta.Outbound indirect flight with Delta, departs from Fort Myers Southwest Florida Reg on Thu., Nov. 26, arriving in Chicago Midway.Price includes taxes and charges.From C$218, select.
Chicago.C$225 per passenger.Departing Wed., Jun. 24.One-way flight with Breeze Airways.Outbound indirect flight with Breeze Airways, departs from Fort Myers Southwest Florida Reg on Wed., Jun. 24, arriving in Chicago Midway.Price includes taxes and charges.From C$225, select.
Chicago.C$229 per passenger.Departing Tue., Jun. 30.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Tue., Jun. 30, arriving in Chicago Midway.Price includes taxes and charges.From C$229, select.
Chicago.C$232 per passenger.Departing Wed., Dec. 2.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Wed., Dec. 2, arriving in Chicago Midway.Price includes taxes and charges.From C$232, select.
Chicago.C$275 per passenger.Departing Thu., Nov. 26.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Thu., Nov. 26, arriving in Chicago Midway.Price includes taxes and charges.From C$275, select.

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

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Fort Myers Southwest Florida Reg to Chicago Midway flights are currently cheapest in September.
Jun.
from C$225
Jul.
from C$204
Aug.
from C$203
Sep.
from C$130
Oct.
from C$204
Nov.
from C$218
Dec.
from C$218
Jan.
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Feb.
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Mar.
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Apr.
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May
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Which airlines fly from Fort Myers Southwest Florida Reg to Chicago Midway?

Fort Myers Southwest Florida Reg to Chicago Midway: Alternative routes

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

Chicago Midway

14km from central Chicago
ClosestCheapest
from C$130
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Chicago O'Hare International

25km from central Chicago
from C$171
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Chicago Dupage County

51km from central Chicago
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Chicago Rockford

126km from central Chicago
from C$196
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Fort Myers to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$130
Cheapest month to flySeptember
Average flight time2 hrs, 53 mins
Most popular airlineSouthwest Airlines
Average flights per week24

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

The best price we found for a return flight from Fort Myers Southwest Florida Reg to Chicago Midway is C$316. 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 53 minutes is the average flight time from Fort Myers Southwest Florida Reg to Chicago Midway.
Southwest Airlines flies direct from Fort Myers Southwest Florida Reg to Chicago Midway.
As of June 2026, there are 24 flights per week flying from Fort Myers Southwest Florida Reg to Chicago Midway.
The cheapest month to fly from Fort Myers Southwest Florida Reg to Chicago Midway is usually September.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Fort Myers Southwest Florida Reg Airport to Chicago Midway Airport on Monday, September 21, 2026.
Yes – the average flight time is 2 hours and 53 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 Chicago Midway 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 Chicago 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 Chicago Midway.

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

  • A direct flight from Southwest Florida International Airport to Chicago Midway International Airport takes an average of 2 hours 55 minutes. The timezone in Chicago is UTC-5, so it's 1 hour behind Fort Myers.

  • There are 15 flights from Southwest Florida International Airport to Chicago Midway International Airport weekly. Hop on the 05:20 flight if you want to get going as soon as possible. If you'd prefer to make the most of your day before leaving, the last flight from RSW to MDW is 21:50.

  • Heading away during a peak time like a public holiday? Expect longer queues at security and check-in. Give yourself extra leeway and arrive up to four hours before international flights and two hours before domestic departures.

  • If you want to have a stopover for your flight from Southwest Florida International Airport to Chicago Midway International Airport, simply uncheck 'Direct flights only' and look at all your options. These are the most popular stopovers between RSW and MDW:

    • Detroit Metropolitan Wayne County Airport

    • Hartsfield-Jackson Atlanta International Airport

    • Cleveland Hopkins International Airport

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

  • The best price we've seen for a one-way ticket from Southwest Florida International Airport to Chicago Midway International Airport is C$130. The cheapest price for a return flight is C$316. Remember that fares can change due to demand when booking.

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

  • The cheapest month for flight tickets from Southwest Florida International Airport to Chicago Midway International Airport is May. Use the 'Whole month' tool to find the lowest prices if you have flexible dates.

  • Log into your online account or use the app to create a Price Alert. We'll notify you straight away if there's a better deal on this route. It doesn't take long, and it'll save you time searching for cheap flight tickets from RSW to MDW every day.

  • Use filters to find the perfect trip for you. To see the 'Fastest,' 'Cheapest' or 'Best' flights from Southwest Florida International Airport to Chicago Midway International Airport, use the 'Sort by' function. You can also filter results by airline, departure and arrival times, and journey duration.

Handy information about Southwest Florida International Airport (RSW)

Arriving at Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • Chicago Midway International Airport to central Chicago is around 21 minutes in a car. It's approximately 19 kilometres away. Discover what options are available, such as cabs, car rentals or ride-sharing.

  • Traveling to the center on public transport will take you roughly 46 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • The quietest month for a flight from Southwest Florida International Airport to Chicago Midway International Airport is May, while July is the most popular. Pick the ideal time to go to Chicago based on whether you prefer a laid-back vibe or a more bustling atmosphere.

  • Lock in your flight from Southwest Florida International Airport to Chicago Midway International Airport for July if you'd like to explore Chicago during its warmest month. Expect temperatures of between 15ºC and 29ºC.

  • Search for cheap flight tickets from RSW to MDW in January if you want to travel in cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC and 3ºC on average.

More about Chicago

Complete your Chicago trip with hotels and a car rental

  • Comparing flights is not the only thing we do. Once you've secured your cheap ticket to Chicago Midway International Airport, explore our great car rental offers that'll give you the freedom to see the sights at your own pace. Then, take a look at our exclusive rates for hotels to find the perfect Chicago stay.

Plan the rest of your trip from Fort Myers to Chicago

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