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Cheap Flights from Chicago Midway to Fort Myers Southwest Florida Reg

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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 to Fort Myers Southwest Florida Reg? Find the lowest prices on one-way and return tickets right here.
Fort Myers.R 1,599 per passenger.Departing Sat, 21 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 21 Jun, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 1,599, select.
Fort Myers.R 1,599 per passenger.Departing Tue, 15 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 15 Jul, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 1,599, select.
Fort Myers.R 1,955 per passenger.Departing Wed, 20 Aug.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 20 Aug, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 1,955, select.
Fort Myers.R 2,502 per passenger.Departing Wed, 20 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 20 Aug, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 2,502, select.
Fort Myers.R 2,502 per passenger.Departing Sat, 31 May.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 31 May, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 2,502, select.
Fort Myers.R 3,557 per passenger.Departing Sat, 27 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 27 Sep, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 3,557, select.
Fort Myers.R 3,699 per passenger.Departing Thu, 23 Oct.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 23 Oct, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 3,699, select.
Fort Myers.R 4,033 per passenger.Departing Mon, 23 Mar.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 23 Mar, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 4,033, 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 June.
May
from R 2,502
Jun
from R 1,599
Jul
from R 1,599
Aug
from R 1,955
Sep
from R 3,557
Oct
from R 3,699
Nov
Find prices
Dec
Find prices
Jan
from R 4,061
Feb
Find prices
Mar
from R 4,033
Apr
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Direct flights 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.

Chicago to Fort Myers: Flight information

The things to know before you go.
Cheapest flight foundR 1,599
Cheapest month to flyJuly
Average flight time2 hrs, 45 mins
Most popular airlineSouthwest Airlines
Average flights per week18

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 R 3,371. 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 May 2025, there are 18 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 May 2025.
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 Saturday, 14 June 2025.
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.

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

  • Around 2 hours 45 minutes is how long you'll be travelling on a direct flight from Chicago Midway International Airport to Southwest Florida International Airport.

  • Fort Myers is one hour ahead of Chicago and observes the UTC-4 timezone.

  • You can choose from 15 weekly Chicago Midway International Airport to Southwest Florida International Airport flights. The 05:20 departure with Southwest Airlines is the earliest flight available. Southwest Airlines operates the last service of the day at 20:45.

  • To ensure you catch your MDW to RSW flight, leave enough time to check in and drop off your luggage. Arriving two hours before international departures and an hour before domestic flights is the standard rule.

  • Travelling during a peak month such as July? Major public holidays and other popular seasons can result in longer queues and delays at airport checkpoints. Play things extra safe and arrive up to four hours ahead of an international flight and two hours before a domestic departure.

  • Getting to Fort Myers (and then seeing more of United States!) is a breeze with Southwest Airlines. This popular carrier offers direct flights from Chicago Midway International Airport to Southwest Florida International Airport.

  • Southwest Airlines has the highest passenger demand on this route.

  • Southwest Airlines is the most punctual carrier offering MDW to RSW flights. A reliable 80.54% of its services on this route arrive without delay.

  • If you'd like to break up your flight, just uncheck 'Direct flights only' when searching for your ticket from Chicago Midway International Airport to Southwest Florida International Airport. These are the most popular stopovers between MDW and RSW:

    • Hartsfield-Jackson Atlanta International Airport

    • Charlotte Douglas 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 cheapest price we've seen for a one-way Chicago Midway International Airport to Southwest Florida International Airport flight is R 1,599. A round-trip ticket right now is R 3,371. Depending on the availability when you book, these fares may change.

  • Get cheap tickets from MDW to RSW by booking six months ahead. Based on our research, that's the sweet spot for landing a bargain.

  • Plan your trip for May. That's the cheapest month for flights from Chicago Midway International Airport to Southwest Florida International Airport. If you're flexible with your dates, use the 'Whole month' tool to see the cheapest airfare across each month.

  • Stay on top of deals for cheap flights from MDW to RSW by creating a Price Alert. You'll get an email or notification on the app when a lower fare pops up.

  • Secure the right flight for you by using the filters. To see the 'Cheapest,' 'Fastest' or 'Best' flights from Chicago Midway International Airport to Southwest Florida International Airport, use the 'Sort by' function. You can also filter results by arrival and departure times, airline, and number of stops.

Handy information about Chicago Midway International Airport (MDW)

  • MDW is located at 5700 South Cicero.

  • When it comes to the on-time performance of Chicago Midway International Airport, data shows 77.88% of flights arrive within the expected timeframe.

  • Central Chicago to Chicago Midway International Airport is around 19 kilometres. Depending on traffic, it'll take about 20 minutes to get there if you're driving, ride-sharing or catching a cab.

  • You can expect a trip time of roughly 45 minutes on public transport.

  • Get your holiday off to a hassle-free start by staying near MDW. Whether you've booked an early flight from Chicago Midway International Airport to Southwest Florida International Airport or just don't like being rushed, these hotels are perfect:

Arriving at Southwest Florida International Airport (RSW)

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

  • You'll find RSW at 11000 Terminal Access Road.

  • Southwest Florida International Airport to the centre of Fort Myers has a drive time of around 25 minutes. It's approximately 23 kilometres away.

When to fly to Southwest Florida International Airport (RSW)

  • It's time to plan your trip dates for your flight from Chicago Midway International Airport to Southwest Florida International Airport. October is the busiest month to head to Fort Myers. If you want a more relaxed vibe, go in May.

  • When reserving your flight from Chicago Midway International Airport to Southwest Florida International Airport, think about the kind of weather you enjoy. August is the warmest month in Fort Myers, with the temperature ranging from 25ºC (77ºF) to 33ºC (91ºF).

  • For cooler conditions, search for a cheap ticket from MDW to RSW in January. Temperatures average between 10ºC (50ºF) and 24ºC (75ºF) then.

Explore more of United States

  • You've visited Fort Myers, now it's time to explore more of United States. Travel about 418 kilometres north to Jacksonville to check off its top attractions. From Jacksonville Zoo and Gardens to The Cummer Museum of Art & Gardens and Friendship Fountain, you've got a jam-packed schedule ahead.

  • Miami is another essential stop in United States and is around 193 kilometres south-east of Fort Myers. No trip is complete without a visit to Wynwood Walls, Vizcaya Museum and Gardens and American Airlines Arena.

Plan the rest of your trip from Chicago to Fort Myers

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.