Cheap Flight Tickets from Chicago (MDW) to Fort Myers (RSW), Starting at $295

Good to Know: Cheapest and Fastest MDW - RSW Flights

Useful information for finding best airline tickets from Chicago Midway International to Southwest Florida International on your next trip.

Cheapest Round Trip Flight

$577

WN Southwest Airlines • nonstop • 4h 10m

Jul 22 – Jul 26

The cheapest round trip flight from Chicago to Fort Myers (MDW-RSW-MDW) is currently $577

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Cheapest Direct Flight

$483

WN Southwest Airlines • nonstop • 4h 10m

Jul 21

The cheapest nonstop flight from Chicago to Fort Myers (MDW-RSW) is currently $483

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Fastest Flight

4h 10m

The fastest nonstop flight from Chicago to Fort Myers (MDW-RSW) takes 4h 10m

Top Airlines Flying from Chicago to Fort Myers

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

Latest Flight Deals from Chicago (MDW) to Fort Myers (RSW)

Compare and book low fare round-trip air tickets from Chicago to Fort Myers. Ideal for travelers with confirmed return itineraries.

Jul 22 - Jul 26, Economy
WN
Chicago → Fort Myers
4h 10m
7:40 AM - 11:30 AM • nonstop
WN
Chicago → Fort Myers
4h 10m
7:20 AM - 9:10 AM • nonstop
$577
Southwest Airlines
Jul 22 - Jul 26, Economy
WN
Chicago → Fort Myers
13h 45m
11:50 AM - 9:15 PM • 1 stop
WN
Chicago → Fort Myers
4h 10m
7:20 AM - 9:10 AM • nonstop
$587
Southwest Airlines
Jul 22 - Jul 26, Economy
WN
Chicago → Fort Myers
4h 10m
1:15 PM - 5:05 PM • nonstop
WN
Chicago → Fort Myers
10h 10m
9:35 AM - 2:45 PM • 1 stop
$587
Southwest Airlines
Jul 22 - Jul 26, Economy
WN
Chicago → Fort Myers
4h 10m
6:55 PM - 10:45 PM • nonstop
WN
Chicago → Fort Myers
12h 15m
6:30 AM - 1:05 PM • 2 stops
$592
Southwest Airlines
Jul 22 - Jul 26, Economy
WN
Chicago → Fort Myers
4h 10m
7:40 AM - 11:30 AM • nonstop
WN
Chicago → Fort Myers
12h 15m
6:30 AM - 1:05 PM • 2 stops
$592
Southwest Airlines
Jul 22 - Jul 26, Economy
WN
Chicago → Fort Myers
12h 25m
1:10 PM - 9:55 PM • 2 stops
WN
Chicago → Fort Myers
4h 10m
7:20 AM - 9:10 AM • nonstop
$592
Southwest Airlines

Fly from Chicago to Fort Myers with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Fort Myers? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to Fort Myers Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to RSW?
The most popular airline flying from Chicago to Fort Myers are
Can I fly from MDW to RSW non-stop?
Yes, you can fly MDW to RSW non-stop on
Which airlines fly nonstop between Chicago and Fort Myers?
The non-stop flights between Chicago and Fort Myers are .
What’s the earliest departure time from MDW to RSW Airport?
The earliest flight leaves MDW at 7:40 am and lands in RSW - Southwest Florida International
What are the airports in Fort Myers?
RSW
Can I make changes to my Chicago to Fort Myers flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from MDW to RSW?
Read the fare rules of the Chicago to Fort Myers air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and Fort Myers?
operate flights between Chicago and Fort Myers
How long does a flight from Chicago to Fort Myers take?
It takes approximately 3 hour to fly non-stop from MDW to RSW, which is 1105.1 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to Fort Myers (RSW) ?
In the past couple of days, the cheapest tickets to RSW from MDW were found on WN : USD 592
Do I need a passport to fly between MDW and RSW?
No
What’s the latest departure time from MDW to RSW ?
The last flight leaves MDW at 12:000 pm

Chicago (MDW) to Fort Myers (RSW): Airport Information

Origin Airport Chicago Midway International , Chicago, US
Destination Airport Southwest Florida International , Fort Myers, US
Distance 1105 miles

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