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Cheap Flights from Fort Myers Southwest Florida Reg to Chicago

Compare Fort Myers Southwest Florida Reg to Chicago flight deals

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Flight deals from Fort Myers Southwest Florida Reg to Chicago

Looking for a cheap last-minute deal or the best return flight from Fort Myers Southwest Florida Reg Airport to Chicago? If you want to travel next month, return fares start from Rs58,992. Find the lowest prices on one-way and return tickets right here.
Chicago.Rs34,704 per passenger.Departing Sat, 16 May.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Fort Myers Southwest Florida Reg on Sat, 16 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs34,704, select.
Chicago.Rs40,488 per passenger.Departing Tue, 1 Sep.One-way flight with United.Outbound direct flight with United departs from Fort Myers Southwest Florida Reg on Tue, 1 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs40,488, select.
Chicago.Rs40,527 per passenger.Departing Tue, 2 Jun.One-way flight with United.Outbound direct flight with United departs from Fort Myers Southwest Florida Reg on Tue, 2 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs40,527, select.
Chicago.Rs40,596 per passenger.Departing Wed, 1 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Wed, 1 Jul, arriving in Chicago Midway.Price includes taxes and charges.From Rs40,596, select.
Chicago.Rs40,724 per passenger.Departing Wed, 26 Aug.One-way flight with United.Outbound direct flight with United departs from Fort Myers Southwest Florida Reg on Wed, 26 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs40,724, select.
Chicago.Rs41,153 per passenger.Departing Sat, 9 Jan.One-way flight with American Airlines.Outbound direct flight with American Airlines departs from Fort Myers Southwest Florida Reg on Sat, 9 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs41,153, select.
Chicago.Rs41,265 per passenger.Departing Mon, 12 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Mon, 12 Oct, arriving in Chicago Midway.Price includes taxes and charges.From Rs41,265, select.
Chicago.Rs43,952 per passenger.Departing Mon, 28 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Fort Myers Southwest Florida Reg on Mon, 28 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs43,952, select.
Chicago.Rs53,979 per passenger.Departing Mon, 28 Dec.One-way flight with United.Outbound direct flight with United departs from Fort Myers Southwest Florida Reg on Mon, 28 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs53,979, select.

Find the cheapest month to fly from Fort Myers Southwest Florida Reg to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Fort Myers Southwest Florida Reg to Chicago flights are currently cheapest in May.
May
from Rs34,704
Jun
from Rs40,527
Jul
from Rs40,596
Aug
from Rs40,724
Sep
from Rs40,488
Oct
from Rs41,265
Nov
Find prices
Dec
from Rs43,952
Jan
from Rs41,153
Feb
Find prices
Mar
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Apr
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Direct flights from Fort Myers Southwest Florida Reg to Chicago

Alternative Fort Myers Southwest Florida Reg to Chicago routes

Looking for the cheapest, fastest or easiest route from Fort Myers Southwest Florida Reg to Chicago? You could fly into the following airports instead.

Chicago Midway

14km from central Chicago
Closest
from Rs38,984
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from Rs34,704
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from Rs47,615
Search flights

Fort Myers to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs34,704
Cheapest month to flyMay
Average flight time3 hrs, 8 mins
Most popular airlineAmerican Airlines
Average flights per week176

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

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Fort Myers Southwest Florida Reg to Chicago is Rs58,992. 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.
3 hours and 7 minutes is the average flight time from Fort Myers Southwest Florida Reg to Chicago.
American Airlines, Southwest Airlines and Alaska Airlines fly direct from Fort Myers Southwest Florida Reg to Chicago.
As of May 2026, there are 176 flights per week flying from Fort Myers Southwest Florida Reg to Chicago.
The cheapest month to fly from Fort Myers Southwest Florida Reg to Chicago is usually June.
If you're flying from Fort Myers Southwest Florida Reg Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from Rs58,992.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Fort Myers Southwest Florida Reg Airport to Chicago on Tuesday, 2 June 2026.
Yes – the average flight time is 3 hours and 7 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 Chicago 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In May, the average temperature is usually around 13°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, United and Frontier Airlines offer the cheapest flight tickets to Chicago.

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

  • The average duration of a direct flight from Southwest Florida International Airport to Chicago is 3 hours.

  • Southwest Florida International Airport is located in Fort Myers. Following the UTC-5 timezone, Chicago is one hour behind Fort Myers.

  • Southwest Florida International Airport (RSW) to O'Hare International Airport (ORD) is the most popular route, with 51 flights a week to choose from. If you have things to do before leaving, the last flight from RSW to ORD is with Spirit Airlines at 21:46. Go for the first departure with American Airlines at 05:53 if you want to get on your way earlier.

  • For stress-free travel, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This will give you enough time to catch your RSW to Chicago flight.

  • Delays at security and check-in are likely if you're heading away during high season, so allow some extra breathing space. A good rule of thumb for peak periods? Arrive up to four hours early for international flights and at least two hours for domestic departures.

  • You can book a direct Southwest Florida International Airport to Chicago ticket. Begin your journey at RSW and arrive at O'Hare International Airport (ORD).

  • A range of airlines offer direct flights from Southwest Florida International Airport to Chicago. The most popular include:

  • RSW is around 16 kilometres from central Fort Myers. If you're catching a cab, ride-sharing or driving from the centre, it'll take you 25 minutes or so to get there, depending on traffic conditions.

  • Want a relaxed start to your travels? Stay near RSW. Whether you're catching an early flight from Southwest Florida International Airport to Chicago or want to avoid feeling rushed, these hotels put convenience first:

  • 77.32% of flights taking off from Southwest Florida International Airport make it to their destination on schedule.

  • RSW is located at 11000 Terminal Access Road.

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

  • The lowest price we've found for a one-way Southwest Florida International Airport to Chicago flight is Rs34,704. The cheapest price for a return flight is Rs58,992. Keep in mind fares can change due to availability at the time of booking.

  • To pick up cheap flights from RSW to Chicago, reserve your journey one month ahead of your departure date.

  • Organise your trip for May. That's the best month for landing a bargain on Southwest Florida International Airport to Chicago tickets. If you're flexible on when you fly, use the 'Whole month' tool to find the cheapest price across every month.

  • There's no need to check back constantly to see if fares have dropped when you set up a Price Alert. We'll update you when there's an extra saving on cheap flights from RSW to Chicago.

  • Select your preferred arrival and departure times, number of stops and airlines with our filters. Then, sort the results for your flight from Southwest Florida International Airport to Chicago by 'Cheapest,' 'Fastest' or 'Best.'

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It'll take you around 35 minutes to reach the centre driving.

  • If you're travelling by public transport, expect a journey time of around 55 minutes.

  • The last thing you need is a long journey to your hotel if you're landing late on a flight from Southwest Florida International Airport to Chicago. Book one of these accommodation options near ORD instead:

  • Hit the road running by picking up an O'Hare International Airport rental car. Grab a set of wheels from Routes Car Rentals, Dollar or Budget to explore Chicago and beyond.

  • Lock in the best possible rate by booking your vehicle from O'Hare International Airport around four weeks before your flight from RSW to Chicago.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • After your flight from Southwest Florida International Airport to Chicago has hit the runway, you can make your way to the city centre in around 20 minutes by car. Central Chicago is roughly 19 kilometres from Chicago Midway International Airport (MDW).

  • Public transport will get you there in around 45 minutes.

  • Hang the 'Do not disturb' sign on your door and rest at a hotel close to MDW. Here are a few options where you can take a load off after your RSW to Chicago flight:

  • Dollar, Hertz and Budget make picking up a Chicago Midway International Airport rental car quick and easy. These suppliers are located in or around the terminal and will have you behind the wheel before you know it.

  • Lock in the lowest price by reserving your ride from MDW four weeks in advance. You can also expect to have a greater range of vehicles.

  • Chicago Midway International Airport is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 137 kilometres from central Chicago. It takes about 1 hour 25 minutes to get to the city centre by cab or ride-share once you've hopped off your flight from Southwest Florida International Airport to Chicago.

  • The journey will take you around 4 hours 15 minutes when travelling on public transport.

  • If you don't want to make your way to the centre, choose a hotel near RFD. Get settled at one of these stays after your RSW to Chicago flight:

  • Stay in control of the next chapter of your journey by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National are dependable companies for booking.

  • Rental companies sometimes offer discounts on early bookings, so book your vehicle from RFD a few weeks in advance of your flight from Southwest Florida International Airport to Chicago. A little prep work can make a big difference in cost.

  • The address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your trip dates before locking in your flight from Southwest Florida International Airport to Chicago. The city comes alive in high season, but rates are generally higher and top attractions can be busy. Go to Chicago in the low season if you want a quieter vibe.

  • When booking your Southwest Florida International Airport to Chicago flight ticket, think about the type of weather you enjoy. July is the warmest month in Chicago, with temperatures ranging from 15ºC to 29ºC.

  • January has average temperatures of between -12ºC and 3ºC. Search for a cheap ticket from RSW to Chicago around that time if you'd rather travel in cooler conditions.

More about Chicago

Explore more of United States

  • You've done Chicago, now it's time to discover other parts of United States. Travel around 451 kilometres south-east to Columbus to tick off its top attractions. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you've got a jam-packed schedule ahead.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. Start your sightseeing at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Fort Myers to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.