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70 € Cheap Flights from Chicago to Fort Myers Southwest Florida Reg

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

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? Find the lowest prices on one-way and return tickets right here.
Fort Myers.70 € per passenger.Departing Wed, 6 Aug, returning Sat, 30 Aug.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Wed, 6 Aug, arriving in Fort Myers Southwest Florida Reg.Inbound direct flight with Spirit Airlines departs from Fort Myers Southwest Florida Reg on Sat, 30 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 70 €, select.
Fort Myers.84 € per passenger.Departing Mon, 29 Sep, returning Fri, 17 Oct.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Mon, 29 Sep, arriving in Fort Myers Southwest Florida Reg.Inbound direct flight with Spirit Airlines departs from Fort Myers Southwest Florida Reg on Fri, 17 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From 84 €, select.
Fort Myers.84 € per passenger.Departing Wed, 8 Oct, returning Fri, 17 Oct.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Wed, 8 Oct, arriving in Fort Myers Southwest Florida Reg.Inbound direct flight with Spirit Airlines departs from Fort Myers Southwest Florida Reg on Fri, 17 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From 84 €, select.
Fort Myers.84 € per passenger.Departing Wed, 15 Oct, returning Sat, 1 Nov.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Wed, 15 Oct, arriving in Fort Myers Southwest Florida Reg.Inbound direct flight with Spirit Airlines departs from Fort Myers Southwest Florida Reg on Sat, 1 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From 84 €, select.
Fort Myers.86 € per passenger.Departing Wed, 13 Aug, returning Tue, 2 Sep.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Wed, 13 Aug, arriving in Fort Myers Southwest Florida Reg.Inbound direct flight with Spirit Airlines departs from Fort Myers Southwest Florida Reg on Tue, 2 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 86 €, select.
Fort Myers.86 € per passenger.Departing Wed, 3 Sep, returning Sun, 7 Sep.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Wed, 3 Sep, arriving in Fort Myers Southwest Florida Reg.Inbound direct flight with Spirit Airlines departs from Fort Myers Southwest Florida Reg on Sun, 7 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 86 €, select.
Fort Myers.86 € per passenger.Departing Sun, 2 Nov, returning Sat, 8 Nov.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Sun, 2 Nov, arriving in Fort Myers Southwest Florida Reg.Inbound direct flight with Spirit Airlines departs from Fort Myers Southwest Florida Reg on Sat, 8 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From 86 €, select.
Fort Myers.88 € per passenger.Departing Wed, 30 Jul, returning Wed, 6 Aug.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Wed, 30 Jul, arriving in Fort Myers Southwest Florida Reg.Inbound direct flight with Spirit Airlines departs from Fort Myers Southwest Florida Reg on Wed, 6 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 88 €, 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 August.
Jul
from 102 €
Aug
from 70 €
Sep
from 86 €
Oct
from 84 €
Nov
from 86 €
Dec
from 153 €
Jan
from 185 €
Feb
from 365 €
Mar
from 365 €
Apr
from 365 €
May
from 365 €
Jun
Find prices

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 found70 €
Cheapest month to flyAugust
Average flight time2 hrs, 53 mins
Most popular airlineAmerican Airlines
Average flights per week302

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

The best price we found for a return flight from Chicago to Fort Myers Southwest Florida Reg is 70 €. 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 53 minutes is the average flight time from Chicago to Fort Myers Southwest Florida Reg.
American Airlines, Alaska Airlines and Southwest Airlines fly direct from Chicago to Fort Myers Southwest Florida Reg.
As of July 2025, there are 302 flights per week flying from Chicago to Fort Myers Southwest Florida Reg.
The cheapest month to fly from Chicago to Fort Myers Southwest Florida Reg is usually August.
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 Wednesday, 6 August 2025.
Yes – the average flight time is 2 hours and 53 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.
The cheapest airline that flies to Fort Myers Southwest Florida Reg is Spirit Airlines .

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

  • Your adventure gets underway at one of Chicago's main airports, O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Explore your options for booking a flight from Chicago to Southwest Florida International Airport (RSW) taking off from either of these.

  • Around 3 hours is how long you'll be in the air on a direct Chicago to Southwest Florida International Airport flight.

  • Fort Myers is one hour ahead of Chicago. Southwest Florida International Airport is located in Fort Myers, which runs on the UTC-4 timezone.

  • The busiest route is from O'Hare International Airport (ORD) to Southwest Florida International Airport (RSW), with 51 direct weekly services. If you want to be on your way right away, the earliest flight from ORD to RSW is the 6am United Airlines service. If a later flight fits your day better, the final departure is at 8:50pm with Frontier Airlines.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for hassle-free flying. Get to the airport on time to catch your flight from Chicago to RSW.

  • During high season, expect longer queues and get there earlier. Aim for at least two hours ahead for domestic flights and up to four hours for international trips.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) will have you travelling directly to your destination. Nonstop flights from Chicago to Southwest Florida International Airport (RSW) can be booked from this terminal.

  • Choose from a variety of carriers that operate direct flights from Chicago to Southwest Florida International Airport departing from ORD. Head off on your trip with any of these:

  • United Airlines ranks first in bookings for flights from ORD to RSW.

  • Among carriers operating on this route, United Airlines has the highest rate of on-time arrivals.

  • Located around 40 kilometres from central Chicago, ORD can be reached in about 35 minutes by car, depending on traffic. The journey by public transport takes roughly 55 minutes.

  • Looking for a convenient hotel near O'Hare International Airport? If you've booked an early flight from Chicago to Southwest Florida International Airport, these stays will put you just around the corner from the terminal:

  • 74.85% of flights that depart O'Hare International Airport land at their destination on time.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Consider flying out of Chicago Midway International Airport (MDW). You can book a direct Chicago to Southwest Florida International Airport (RSW) plane ticket from this hub.

  • From MDW, direct flights from Chicago to RSW are offered by Southwest Airlines.

  • Southwest Airlines is the top choice for passengers flying from MDW to RSW.

  • Choose Southwest Airlines if you're looking for punctuality. Its flights between Chicago Midway International Airport and Southwest Florida International Airport arrive as scheduled 80.54% of the time.

  • On public transport, you can travel from central Chicago to MDW in about 45 minutes. The terminal is roughly 19 kilometres away, and getting there by car takes approximately 20 minutes.

  • Want to enjoy an extra night away before catching your Chicago to RSW flight? Check in to a hotel near Chicago Midway International Airport before your holiday officially starts. These stays have a room with your name on it:

  • 77.88% of all departures from Chicago Midway International Airport make it to their destination as expected.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is roughly 137 kilometres from central Chicago. The drive from the city centre to the airport takes about 1 hour 25 minutes. If you're considering public transport, expect a journey time of around 4 hours 15 minutes.

  • Sleep a little longer, move a little slower, and still make your Chicago to Southwest Florida International Airport flight without having to rush. These accommodation options near Chicago Rockford International Airport make departure day effortless if you're setting off early:

  • Flights departing from RFD arrive at their destination within the scheduled time frame 76.19% of the time.

  • You'll find Chicago Rockford International Airport at 2 Airport Cir.

About Southwest Florida International Airport (RSW)

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

  • 43 € is the lowest price for a one-way ticket from Chicago to Southwest Florida International Airport. Return flights start at 70 €. These fares may change depending on availability and demand.

  • To find cheap flights from Chicago to RSW, book in advance. Airlines generally offer the most competitive fares when flights first go on sale.

  • If you have some flexibility with your travel plans, try using the 'Whole month' search tool. It'll give you the cheapest price across the month when searching for your Chicago to Southwest Florida International Airport ticket.

  • Save time looking for cheap plane tickets from Chicago to RSW by creating a Price Alert. We'll send you an email or notification through the app when fares go down.

  • Save on your flight from Chicago to Southwest Florida International Airport by using the search filters. Choose your preferred departure time, duration and airlines, then sort the results by 'Cheapest' for the best deals.

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

  • Think about the pace you're looking for when picking your flight dates. May is the quietest month to go to Fort Myers. October is when most people book flights from Chicago to Southwest Florida International Airport (RSW), which may be ideal if you'd rather travel when it's busy.

  • The warmest month in Fort Myers is August, with temperatures ranging between 25ºC (77ºF) and 33ºC (91ºF). Lock in your Chicago to RSW plane ticket then if that's your idea of comfortable weather.

  • Look for cheap tickets from Chicago to Southwest Florida International Airport in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between 10ºC (50ºF) and 24ºC (75ºF).

More about Fort Myers

Explore more of the United States

  • You've done Fort Myers, now it's time to discover other parts of the United States. Journey about 177 kilometres south-east to Miami to check off its leading attractions. From Ocean Drive to Beach and La Playa De Miami, you'll have a packed itinerary ahead.

  • Around 177 kilometres north-west of Fort Myers, Tampa is another favourite stop in the United States. Experience this destination's highlights firsthand at Super Bowl, Busch Gardens Tampa and The Florida Aquarium.

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.