Cheap Flight Tickets from Chicago (MDW) to Fort Myers (RSW), Starting at $415

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

$523

WN Southwest Airlines • nonstop • 4h 10m

Jul 07 – Jul 07

The cheapest round trip flight from Chicago to Fort Myers (MDW-RSW-MDW) is currently $523

🔍 Search Flights

Cheapest Direct Flight

$415

WN Southwest Airlines • nonstop • 4h 10m

Jul 07

The cheapest nonstop flight from Chicago to Fort Myers (MDW-RSW) is currently $415

🔍 Search Flights

Fastest Flight

4h 5m

The fastest nonstop flight from Chicago to Fort Myers (MDW-RSW) takes 4h 5m

Top Airlines Flying from Chicago to Fort Myers

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta 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 07 - Jul 07, Economy
WN
Chicago → Fort Myers
4h 10m
7:40 AM - 11:30 AM • nonstop
WN
Chicago → Fort Myers
4h 10m
6:25 PM - 8:15 PM • nonstop
$523
Southwest Airlines
Jul 07 - Jul 07, Economy
DL
Chicago → Fort Myers
8h 31m
6:00 AM - 12:11 PM • 1 stop
DL
Chicago → Fort Myers
7h 28m
6:27 PM - 10:15 PM • 1 stop
$542
Delta Airlines
Jul 07 - Jul 07, Economy
WN
Chicago → Fort Myers
7h 5m
8:20 AM - 1:45 PM • 1 stop
WN
Chicago → Fort Myers
7h 25m
6:55 PM - 10:40 PM • 1 stop
$542
Southwest Airlines
Jul 07 - Jul 07, Economy
WN
Chicago → Fort Myers
4h 10m
7:40 AM - 11:30 AM • nonstop
WN
Chicago → Fort Myers
32h 20m
5:20 PM - 12:00 PM • 2 stops
$749
Southwest Airlines
Jul 07 - Jul 07, Economy
DL
Chicago → Fort Myers
12h 15m
6:00 AM - 2:35 PM • 1 stop
UA
Chicago → Fort Myers
5h 21m
4:39 PM - 7:00 PM • nonstop
$862
Delta Airlines
Jul 07 - Jul 07, Economy
DL
Chicago → Fort Myers
8h 31m
6:00 AM - 12:11 PM • 1 stop
UA
Chicago → Fort Myers
5h 21m
4:39 PM - 7:00 PM • nonstop
$868
Delta 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 6:00 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 749
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 6:55 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

More Flight Options for Chicago (MDW) and Fort Myers (RSW)

Why Fareleaders for MDW to RSW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Chicago to Fort Myers flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on MDW to RSW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Chicago to Fort Myers flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Chicago (MDW) to Fort Myers (RSW)
Terms and Conditions*