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£156 Cheap Flights from Chicago (ORD) to Fort Myers (RSW)

View £156 flight on Tue, 28 Jul 2026Opens in a new window

Popular airlines from Chicago O'Hare International Airport (ORD) to Southwest Florida Intl. Airport (RSW)

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Cheap Flights from Chicago (ORD) to Fort Myers (RSW)

Prices were available within the past 7 days and start at £156 for one-way flights and £328 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Sat, 10 Oct - Sat, 17 Oct
ORD
Chicago
RSW
Fort Myers
£328 Return, found 1 day ago
£328
Return
found 1 day ago
Select JetBlue Airways flight, departing Sat, 10 Oct from Chicago to Fort Myers, returning Sat, 17 Oct, priced at £328 found 1 day ago
JetBlue Airways
Sat, 10 Oct - Sat, 17 Oct
ORD
Chicago
RSW
Fort Myers
£361 Return, found 1 day ago
£361
Return
found 1 day ago
Select JetBlue Airways flight, departing Sat, 10 Oct from Chicago to Fort Myers, returning Sat, 17 Oct, priced at £361 found 1 day ago
JetBlue Airways
Sat, 10 Oct - Sat, 17 Oct
ORD
Chicago
RSW
Fort Myers
£439 Return, found 1 day ago
£439
Return
found 1 day ago
Select JetBlue Airways flight, departing Sat, 10 Oct from Chicago to Fort Myers, returning Sat, 17 Oct, priced at £439 found 1 day ago
JetBlue Airways
Sat, 10 Oct - Sat, 17 Oct
ORD
Chicago
RSW
Fort Myers
£454 Return, found 1 day ago
£454
Return
found 1 day ago
Select JetBlue Airways flight, departing Sat, 10 Oct from Chicago to Fort Myers, returning Sat, 17 Oct, priced at £454 found 1 day ago
JetBlue Airways
Sat, 10 Oct - Sat, 17 Oct
ORD
Chicago
RSW
Fort Myers
£466 Return, found 1 day ago
£466
Return
found 1 day ago
Select JetBlue Airways flight, departing Sat, 10 Oct from Chicago to Fort Myers, returning Sat, 17 Oct, priced at £466 found 1 day ago
Alaska Airlines
Wed, 25 Nov - Thu, 3 Dec
ORD
Chicago
RSW
Fort Myers
£471 Return, found 1 day ago
£471
Return
found 1 day ago
Select Alaska Airlines flight, departing Wed, 25 Nov from Chicago to Fort Myers, returning Thu, 3 Dec, priced at £471 found 1 day ago
JetBlue Airways
Sat, 10 Oct - Sat, 17 Oct
ORD
Chicago
RSW
Fort Myers
£472 Return, found 1 day ago
£472
Return
found 1 day ago
Select JetBlue Airways flight, departing Sat, 10 Oct from Chicago to Fort Myers, returning Sat, 17 Oct, priced at £472 found 1 day ago
JetBlue Airways
Sat, 10 Oct - Sat, 17 Oct
ORD
Chicago
RSW
Fort Myers
£474 Return, found 1 day ago
£474
Return
found 1 day ago
Select JetBlue Airways flight, departing Sat, 10 Oct from Chicago to Fort Myers, returning Sat, 17 Oct, priced at £474 found 1 day ago
Alaska Airlines
Wed, 25 Nov - Thu, 3 Dec
ORD
Chicago
RSW
Fort Myers
£475 Return, found 1 day ago
£475
Return
found 1 day ago
Select Alaska Airlines flight, departing Wed, 25 Nov from Chicago to Fort Myers, returning Thu, 3 Dec, priced at £475 found 1 day ago
JetBlue Airways
Sat, 10 Oct - Sat, 17 Oct
ORD
Chicago
RSW
Fort Myers
£488 Return, found 1 day ago
£488
Return
found 1 day ago
Select JetBlue Airways flight, departing Sat, 10 Oct from Chicago to Fort Myers, returning Sat, 17 Oct, priced at £488 found 1 day ago

Find the cheapest month to fly from Chicago (ORD) to Fort Myers (RSW)

February is typically the cheapest month to fly

From £45 - £113 per traveller.

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.) cost?
You can find cheap one-way flights from £156 and cheap return flights from £328 ORD to RSW with Expedia. Return flights often range between £268 and £952. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when ORD to RSW ticket fares go up or down.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
The cheapest months to fly from ORD to RSW are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (ORD) to Fort Myers, FL (RSW)?
Enter ORD to RSW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
United is one of the cheapest airlines offering nonstop return flights from Chicago, IL (ORD-O'Hare Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.), with tickets starting from around £160 for flights that can be booked for departure within the next year. Alaska Airlines offers one of the cheapest connecting return flights from Chicago, IL (ORD-O'Hare Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.) starting from around £206. These prices are per adult, for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from Chicago, IL (ORD) to Fort Myers, FL (RSW)?
To find a cheap flight from Chicago, IL (ORD) to Fort Myers, FL (RSW), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Chicago, IL (ORD) to Fort Myers, FL (RSW)?
Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from Chicago, IL (ORD) to Fort Myers, FL (RSW). To compare more early flights, use the "Early Morning" and "Morning" filters in your search.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Fort Myers, FL (RSW-Southwest Florida Intl.)?
A nonstop flight from ORD to RSW typically takes around 3 hours, covering approximately 1,807 kilometers. Connecting flights on this route usually add 3 hours 50 minutes to your travel time. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD) to Fort Myers, FL (RSW)?
Select the "Business class" and "First class" filters when looking for Chicago, IL (ORD) to Fort Myers, FL (RSW) flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Chicago, IL (ORD) to Fort Myers, FL (RSW) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD) to Fort Myers, FL (RSW) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD) to Fort Myers, FL (RSW) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD) to Fort Myers, FL (RSW) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD) to Fort Myers, FL (RSW) flight and hotel package?
Securing a Chicago, IL (ORD) to Fort Myers, FL (RSW) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD) to Fort Myers, FL (RSW)?
If you booked your Chicago, IL (ORD) to Fort Myers, FL (RSW) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Southwest Florida Intl.
Airlines serving
Alaska Airlines, JetBlue Airways
Return price
£327
Distance
1796 km
Average flight time
4 hours 2 mins

Book with confidence

Compare flights from Chicago to Fort Myers easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Chicago to Fort Myers. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to Southwest Florida Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from O'Hare Intl. to Southwest Florida Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from O'Hare Intl. (ORD) to Southwest Florida Intl. (RSW)

The easiest way to view the best deals on flights from Chicago to Fort Myers today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from O'Hare Intl. to Southwest Florida Intl. start at just £328 and range up to £488.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Chicago and Fort Myers
  • booking your flight during October, the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Chicago to Fort Myers flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from O'Hare Intl. to Southwest Florida Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Compare flights from Chicago to Fort Myers easily and book with confidence

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*Available to Expedia members.