Cheap Flights from Chicago to Fort Myers Southwest Florida Reg

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Compare Chicago 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

Book the best Fort Myers Southwest Florida Reg fare with no extra fees

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Flight deals from Chicago to Fort Myers Southwest Florida Reg

Looking for a cheap last-minute deal or the best return flight from Chicago to Fort Myers Southwest Florida Reg Airport? If you want to travel next month, return fares start from R 4,524. Find the lowest prices on one-way and return tickets right here.

Fort Myers.R 1,367 per passenger.Departing Thu, 3 Dec.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Thu, 3 Dec, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 1,367, select.

Fort Myers.R 1,444 per passenger.Departing Mon, 23 Nov.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Mon, 23 Nov, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 1,444, select.

Fort Myers.R 2,183 per passenger.Departing Thu, 24 Sep.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 24 Sep, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 2,183, select.

Fort Myers.R 2,183 per passenger.Departing Thu, 1 Oct.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 1 Oct, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 2,183, select.

Fort Myers.R 2,262 per passenger.Departing Wed, 28 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 28 Oct, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 2,262, select.

Fort Myers.R 2,262 per passenger.Departing Wed, 16 Sep.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 16 Sep, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 2,262, select.

Fort Myers.R 2,262 per passenger.Departing Mon, 8 Feb.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Mon, 8 Feb, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 2,262, select.

Fort Myers.R 2,262 per passenger.Departing Sat, 9 Jan.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 9 Jan, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 2,262, select.

Fort Myers.R 2,764 per passenger.Departing Sat, 8 May.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 8 May, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 2,764, select.

Fort Myers.R 2,927 per passenger.Departing Fri, 16 Jul.One-way flight with American Airlines.Outbound direct flight with American Airlines departs from Chicago O'Hare International on Fri, 16 Jul, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 2,927, select.

Fort Myers.R 3,085 per passenger.Departing Sat, 27 Mar.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 27 Mar, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 3,085, select.

Fort Myers.R 3,104 per passenger.Departing Sun, 28 Mar.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sun, 28 Mar, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 3,104, select.

Fort Myers.R 3,104 per passenger.Departing Sun, 23 May.One-way flight with American Airlines.Outbound direct flight with American Airlines departs from Chicago O'Hare International on Sun, 23 May, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 3,104, select.

Fort Myers.R 3,441 per passenger.Departing Sat, 29 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 29 Aug, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From R 3,441, select.

Find the cheapest month to fly from Chicago 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 to Fort Myers Southwest Florida Reg flights are currently cheapest in December.

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Direct flights from Chicago to Fort Myers Southwest Florida Reg

Chicago to Fort Myers Southwest Florida Reg: Alternative routes

Compare routes from Chicago 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 found	R 1,367
Cheapest month to fly	December
Average flight time	2 hrs, 55 mins
Most popular airline	American Airlines
Average flights per week	213

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

How much are return flights from Chicago to Fort Myers Southwest Florida Reg?

The best price we found for a return flight from Chicago to Fort Myers Southwest Florida Reg is R 2,648. 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.

How long does it take to fly from Chicago to Fort Myers Southwest Florida Reg?

2 hours and 55 minutes is the average flight time from Chicago to Fort Myers Southwest Florida Reg.

Which airlines fly direct from Chicago to Fort Myers Southwest Florida Reg?

American Airlines, Southwest Airlines and United fly direct from Chicago to Fort Myers Southwest Florida Reg.

How many flights are there a week from Chicago to Fort Myers Southwest Florida Reg?

As of August 2026, there are 213 flights per week flying from Chicago to Fort Myers Southwest Florida Reg.

When is the cheapest time to fly from Chicago to Fort Myers Southwest Florida Reg?

The cheapest month to fly from Chicago to Fort Myers Southwest Florida Reg is usually December.

Which upcoming date is cheapest to fly from Chicago to Fort Myers Southwest Florida Reg Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Fort Myers Southwest Florida Reg Airport on Thursday, 3 December 2026.

Can I get a direct flight from Chicago to Fort Myers Southwest Florida Reg Airport?

Yes – the average flight time is 2 hours and 55 minutes.

How can I find the best flight deal to Fort Myers Southwest Florida Reg?

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.

When is the best time to book flights to Fort Myers?

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.

Which is the cheapest airline to fly from Chicago to Fort Myers Southwest Florida Reg with?

The cheapest airline that flies to Fort Myers Southwest Florida Reg is Frontier Airlines .

Flying from Chicago to Southwest Florida International Airport (RSW): What you need to know

Get your trip planning underway by checking out the best place to catch your flight from Chicago to Southwest Florida International Airport (RSW). Explore your options for leaving from Chicago O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), two of the city's main airports.
Book a direct Chicago to Southwest Florida International Airport flight and you'll be in the air for around 3 hours.
The timezone in Fort Myers is UTC-5, which is one hour ahead of Chicago. Southwest Florida International Airport is located in Fort Myers.
The most popular route is Chicago O'Hare International Airport (ORD) to Southwest Florida International Airport (RSW). There are 57 direct services every week.
Leave plenty of time to make your flight from Chicago to RSW. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.
If you're flying during a peak month like July, head to the airport even earlier. It's smart to arrive up to four hours before an international flight and two hours ahead of domestic departures. You can expect lines to be longer during holiday periods like Thanksgiving and spring break.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

You can jump on a direct flight from Chicago to Southwest Florida International Airport (RSW) leaving from Chicago O'Hare International Airport (ORD).
Direct flights from Chicago to Southwest Florida International Airport are operated by a good number of airlines at ORD. Book your journey with one of these:
United is the airline most travellers choose for flights from ORD to RSW.
The carrier with the top on-time arrival performance on this route is Frontier Airlines.
The journey from central Chicago to ORD takes around 45 minutes on public transport. If you ride-share, drive or take a taxi, you'll cover the 27 kilometres in 30 minutes or so, depending on traffic conditions.
In search of a comfortable hotel near Chicago O'Hare International Airport? If you've booked an early flight from Chicago to Southwest Florida International Airport, these accommodation options will have you sleeping moments from your departure gate:
When it comes to the on-time performance of Chicago O'Hare International Airport, data shows 70% of flights meet their scheduled arrival time.
ORD's address is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Consider starting your trip from Chicago Midway International Airport (MDW). You can book a direct Chicago to Southwest Florida International Airport (RSW) plane ticket with departures from here.
From MDW, direct flights from Chicago to RSW are offered by Southwest Airlines.
Southwest Airlines takes the lead in bookings on the MDW to RSW route.
With 77.6% of its services landing as planned, Southwest Airlines is the top on-time carrier flying between Chicago Midway International Airport and Southwest Florida International Airport.
With public transport, you can travel from central Chicago to MDW in around 30 minutes. The terminal is roughly 16 kilometres away, and making the trip by car takes approximately 25 minutes.
Start your holiday early with an extra night away from home. Before your Chicago to RSW flight, kick back in one of these hotels near Chicago Midway International Airport:
76% of all departures from Chicago Midway International Airport arrive according to schedule.
You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

RFD is around 145 kilometres from central Chicago. Driving from the city centre to the airport takes about 1 hour 40 minutes. If you're planning to use public transport, you can expect a journey of around 2 hours.
Set yourself up for a smooth departure — stay near Chicago Rockford International Airport and know you'll reach the terminal with time to spare. Get settled at one of these hotels the day before if you've booked an early Chicago to Southwest Florida International Airport flight:
The on-time performance rate of RFD is 71%. In other words, that's how often flights from this airport reach their final stop as planned.
The street address of Chicago Rockford International Airport is 2 Airport Cir.

About Southwest Florida International Airport (RSW)

The last thing you need is a lengthy journey to your hotel if you're arriving on a late flight from Chicago to Southwest Florida International Airport. Book one of these accommodation options near RSW instead:
For the lowest price, reserve your vehicle around two weeks ahead of your Chicago to Southwest Florida International Airport flight.
You'll find RSW at 11000 Terminal Access Road.

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

Southwest Florida International Airport is around 27 kilometres from central Fort Myers. It takes around 30 minutes or so to get to the city by car.
Travelling by public transport will take you roughly 1 hour.

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

The lowest price we've found for a one-way ticket from Chicago to Southwest Florida International Airport is R 1,367. For a return flight on this route, the best price is R 2,648. Depending on when you want to go and the availability, these fares could change.
To pick up cheap flights from Chicago to RSW, book early. Airlines generally offer lower prices when tickets are first released.
The 'Whole month' search tool shows you the cheapest Chicago to Southwest Florida International Airport tickets across the month. It's a good way to snap up a bargain if your travel plans aren't set in stone.
Finding a cheap plane ticket from Chicago to RSW is a piece of cake with Price Alerts. Simply create one of these automatic alerts and we'll get in touch as soon as prices go down.
Chase down a great fare on a flight from Chicago to Southwest Florida International Airport with the help of the filters. Pick your preferred arrival and departure times, airlines and number of stops. You can also sort your results by 'Best,' 'Fastest' or 'Cheapest.'

The best time to fly from Chicago to Southwest Florida International Airport (RSW)

October is the quietest month for flights from Chicago to Southwest Florida International Airport (RSW), while March is the busiest. Pick the best time to go to Fort Myers based on whether you prefer a laid-back vibe or a more bustling atmosphere.
Lock in a Chicago to RSW plane ticket departing in August if you want to explore the city during its warmest month. Expect temperatures in Fort Myers to range from 25ºC (77ºF) to 33ºC (91ºF).
January has temperatures of between 10ºC (50ºF) and 24ºC (75ºF). Search for cheap tickets from Chicago to Southwest Florida International Airport around that time if you want to travel when it's cooler.

More about Fort Myers

When it comes to searching for somewhere to lay your head, you'll find the best places to stay in Fort Myers right here. Explore these options once you've booked your flight from Chicago to Southwest Florida International Airport:
Edison & Ford Winter Estates and Burroughs Home & Gardens are a couple of top-rated attractions to add to your Fort Myers to-do list. Keep the sightseeing going at Lakes Regional Park.

Explore more of the United States

Miami is just one of the many cities in the United States waiting to be discovered after you've seen Fort Myers. Around 177 kilometres away to the southeast, its best attractions include Beach, Ocean Drive and Port of Miami.
Tampa is another well-known destination in the United States and is around 177 kilometres northwest of Fort Myers. No trip is complete without dropping by Busch Gardens Tampa, The Florida Aquarium and ZooTampa at Lowry Park.