Flight tickets from Fort Myers Southwest Florida Reg to Chicago

Travellers and cabin class

Compare Fort Myers Southwest Florida Reg to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

Book the best Chicago fare with no extra fees

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 to Chicago? Find the lowest prices on one-way and return tickets right here.

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 March.

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.

Fort Myers to Chicago: Flight information

The things to know before you go.
Cheapest flight found₹ 4,442
Cheapest month to flyMarch
Average flight time3 hrs, 7 mins
Most popular airlineSouthwest Airlines
Average flights per week181

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 ₹ 8,883. 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 6 minutes is the average flight time from Fort Myers Southwest Florida Reg to Chicago.
Southwest Airlines, American Airlines and Alaska Airlines fly direct from Fort Myers Southwest Florida Reg to Chicago.
As of February 2025, there are 181 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 February 2025.
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 ₹ 8,883.
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, 25 March 2025.
Yes – the average flight time is 3 hours and 6 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 February, the average temperature is usually around -2°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, Spirit Airlines offers the cheapest flight tickets to Chicago.

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

  • Take a direct flight from Southwest Florida International Airport to Chicago and you'll be travelling for around 2 hours 55 minutes.

  • Chicago is 1 hour behind Fort Myers, where Southwest Florida International Airport is located. Chicago operates on the UTC-5 timezone.

  • The busiest route is from Southwest Florida International Airport (RSW) to O'Hare International Airport (ORD). You can select from 69 weekly services between these two airports. If you want to get going as soon as possible, the earliest flight from RSW to ORD is the 06:57 American Airlines service. If you'd rather travel later, the final departure is at 20:41 with Spirit Airlines.

  • To ensure you catch your flight from RSW to Chicago, allow plenty of time to check in and find your gate. Turning up two hours ahead of international departures and an hour before domestic flights is the general travel rule.

  • Popular months like October or holiday periods such as Christmas and New Year will mean longer lines at check-in and security. Play it safe and get to the airport even earlier. Arriving two hours before a domestic flight and up four hours ahead of international flights is a smart idea.

  • You can book a direct flight from Southwest Florida International Airport to Chicago that touches down at O'Hare International Airport (ORD).

  • Choose from a variety of carriers that offer direct flights from Southwest Florida International Airport to Chicago. Book your journey with one of these:

  • Once you've booked cheap tickets from Southwest Florida International Airport to Chicago, get your travel documents ready. A passport or visa isn't necessary since you're travelling within United States. As long as you have another valid form of identification, like a driver's licence or an ID card, you're all set.

  • Central Fort Myers to RSW is around 23 kilometres. Depending on traffic, it'll take you about 25 minutes to get there if you're driving, catching a cab or ride-sharing.

  • Booked an early flight from Southwest Florida International Airport to Chicago? Avoid the hassle of rushing to the terminal (and catch some extra z's) by choosing one of these stays close to RSW:

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

  • ₹ 4,442 is the lowest price we've found for a one-way ticket from Southwest Florida International Airport to Chicago. For a return flight on this route, the best price is ₹ 8,883. Depending on when you book and the availability, these fares may change.

  • Book 9 months before you want to fly. After looking at the numbers on our calendar, this is how far you'll want to book ahead to find cheap tickets from RSW to Chicago.

  • Organise your trip for May. That's the cheapest month for tickets from Southwest Florida International Airport to Chicago. If you have flexibility with your dates, use the 'Whole month' tool to find the cheapest price across each month.

  • Set up a Price Alert for flight tickets from RSW to Chicago. There's no need to check every day to find out if fares have dropped. We'll let you know the moment there's a change in price.

  • Use the filters to tailor your flights from Southwest Florida International Airport to Chicago. Simply enter your ideal departure and arrival times, airlines and number of stops. Alternatively, sort your results by 'Cheapest' to see the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to central Chicago is approximately 40 kilometres. It takes around 35 minutes to get to the centre driving.

  • It takes roughly 54 minutes to get there by public transport.

  • If you're coming in on a late flight from Southwest Florida International Airport to Chicago, few things beat the convenience of staying near the terminal. Grab your bags from the carousel and then be showered and snoozing soon after at one of these accommodation options near ORD:

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • It's time to work out your dates for your flight from Southwest Florida International Airport to Chicago. August is the most popular month for a trip to Chicago. If you want a quieter vibe, go in February.

  • Before locking in your flight from Southwest Florida International Airport to Chicago, think about the kind of weather you enjoy. July is the warmest month in Chicago, with the temperature ranging from 15ºC to 29ºC.

  • If you like travelling in cooler conditions, look for a cheap flight from RSW to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

  • When it comes to searching for somewhere to rest your head, you'll find the most popular stays in Chicago right here. Check out these options as soon as you've booked your flight from Southwest Florida International Airport to Chicago:

  • All great journeys should include a little sightseeing. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are must-visits when exploring Chicago.

Complete your Chicago trip with a car rental

  • We use the same magic that helped you find your cheap flight from Southwest Florida International Airport to Chicago to track down deals on car rentals. Search for your ride in seconds and easily compare your options. Plus we give you all the info on car rentals in Chicago, from the most popular car type to the best time to book.

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