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Uncover the best deals on Chicago to Fort Myers flights by comparing fares from hundreds of airlines and agencies.
Good to Know: Cheapest and Fastest CHI - RSW Flights
Useful information for finding best airline tickets from Chicago All Airport to Southwest Florida International on your next trip.
Cheapest Round Trip Flight
$102
Southwest Airlines
• nonstop
• 4h
Sep 19 – Sep 28
The cheapest round trip flight from Chicago to Fort Myers (CHI-RSW-CHI) is currently $102
Cheapest Direct Flight
$97
Southwest Airlines
• nonstop
• 4h 10m
Sep 19
The cheapest nonstop flight from Chicago to Fort Myers (CHI-RSW) is currently $97
Fastest Flight
4h
The fastest nonstop flight from Chicago to Fort Myers (CHI-RSW) takes 4h
Top Airlines Flying from Chicago to Fort Myers
Latest Flight Deals from Chicago (CHI) 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.
Sep 19 - Sep 28, Economy
Chicago → Fort Myers
4h
10:55 AM - 2:35 PM • nonstop
Chicago → Fort Myers
4h 10m
6:50 AM - 8:40 AM • nonstop
Southwest Airlines
Sep 19 - Sep 28, Economy
Chicago → Fort Myers
9h 10m
5:00 AM - 11:50 AM • 1 stop
Chicago → Fort Myers
7h 10m
11:35 AM - 3:05 PM • 1 stop
Southwest Airlines
Sep 19 - Sep 28, Economy
Chicago → Fort Myers
10h 10m
6:35 AM - 1:45 PM • 1 stop
Chicago → Fort Myers
7h 10m
11:35 AM - 3:05 PM • 1 stop
Southwest Airlines
Sep 19 - Sep 28, Economy
Chicago → Fort Myers
12h 25m
7:45 AM - 4:30 PM • 1 stop
Chicago → Fort Myers
7h 10m
11:35 AM - 3:05 PM • 1 stop
Southwest Airlines
Sep 19 - Sep 28, Economy
Chicago → Fort Myers
16h 55m
9:05 AM - 8:20 PM • 1 stop
Chicago → Fort Myers
7h 10m
11:35 AM - 3:05 PM • 1 stop
Southwest Airlines
Flying to Fort Myers soon? We've surfaced some of the most affordable last-minute flights from Chicago to Fort Myers, ideal for urgent plans or spontaneous trips.
Sep 19 - Sep 28, Economy
Chicago → Fort Myers
4h
10:55 AM - 2:35 PM • nonstop
Chicago → Fort Myers
4h 10m
6:50 AM - 8:40 AM • nonstop
Southwest Airlines
Sep 19 - Sep 28, Economy
Chicago → Fort Myers
9h 10m
5:00 AM - 11:50 AM • 1 stop
Chicago → Fort Myers
7h 10m
11:35 AM - 3:05 PM • 1 stop
Southwest Airlines
Sep 19 - Sep 28, Economy
Chicago → Fort Myers
10h 10m
6:35 AM - 1:45 PM • 1 stop
Chicago → Fort Myers
7h 10m
11:35 AM - 3:05 PM • 1 stop
Southwest Airlines
Sep 19 - Sep 28, Economy
Chicago → Fort Myers
12h 25m
7:45 AM - 4:30 PM • 1 stop
Chicago → Fort Myers
7h 10m
11:35 AM - 3:05 PM • 1 stop
Southwest Airlines
Sep 19 - Sep 28, Economy
Chicago → Fort Myers
16h 55m
9:05 AM - 8:20 PM • 1 stop
Chicago → Fort Myers
7h 10m
11:35 AM - 3:05 PM • 1 stop
Southwest Airlines
Looking for the fastest way to Fort Myers? These direct flight options from CHI to RSW offer both convenience and value—no layovers, just straight to your destination.
Sep 19 - Sep 28, Economy
Chicago → Fort Myers
4h 10m
3:05 PM - 6:55 PM • nonstop
Chicago → Fort Myers
4h 10m
6:50 AM - 8:40 AM • nonstop
Southwest Airlines
FAQs on Chicago to Fort Myers Flights
What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from CHI to RSW?
The most popular airline flying from Chicago to Fort Myers are
Can I fly from CHI to RSW non-stop?
Yes, you can fly CHI 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 CHI to RSW Airport?
The earliest flight leaves CHI at 5:00 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 CHI 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 CHI to RSW, which is 1120.28 miles by air.
Which airlines provide the cheapest flights from Chicago (CHI) to Fort Myers (RSW) ?
In the past couple of days, the cheapest tickets to RSW from CHI were found on WN : USD 102
Do I need a passport to fly between CHI and RSW?
No
What’s the latest departure time from CHI to RSW ?
The last flight leaves CHI at 3:05 pm
Chicago (CHI) to Fort Myers (RSW): Airport Information
| Origin Airport | Chicago All Airport, Chicago, US |
| Destination Airport | Southwest Florida International , Fort Myers, US |
| Distance | 1120 miles |
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