$135 Cheap Flights from Fort Myers (RSW) to Chicago (ORD)

View $135 flight on Mon, Oct 12, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $135 for one-way flights and $295 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, Jun 29 - Mon, Jul 6
RSW
Fort Myers
ORD
Chicago
$295 Roundtrip, just found
$295
Roundtrip
just found
Select American Airlines flight, departing Mon, Jun 29 from Fort Myers to Chicago, returning Mon, Jul 6, priced at $295 just found
United
Mon, Jun 29 - Mon, Jul 6
RSW
Fort Myers
ORD
Chicago
$295 Roundtrip, just found
$295
Roundtrip
just found
Select United flight, departing Mon, Jun 29 from Fort Myers to Chicago, returning Mon, Jul 6, priced at $295 just found
American Airlines
Thu, Nov 5 - Tue, Nov 10
RSW
Fort Myers
ORD
Chicago
$303 Roundtrip, found 3 days ago
$303
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Nov 5 from Fort Myers to Chicago, returning Tue, Nov 10, priced at $303 found 3 days ago
American Airlines
Mon, Jun 29 - Mon, Jul 6
RSW
Fort Myers
ORD
Chicago
$305 Roundtrip, just found
$305
Roundtrip
just found
Select American Airlines flight, departing Mon, Jun 29 from Fort Myers to Chicago, returning Mon, Jul 6, priced at $305 just found
American Airlines
Tue, Jul 7 - Sat, Jul 18
RSW
Fort Myers
ORD
Chicago
$307 Roundtrip, found 1 day ago
$307
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 7 from Fort Myers to Chicago, returning Sat, Jul 18, priced at $307 found 1 day ago
American Airlines
Tue, Jun 9 - Wed, Jun 10
RSW
Fort Myers
ORD
Chicago
$311 Roundtrip, found 3 hours ago
$311
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Tue, Jun 9 from Fort Myers to Chicago, returning Wed, Jun 10, priced at $311 found 3 hours ago
American Airlines
Tue, Jun 16 - Thu, Jun 18
RSW
Fort Myers
ORD
Chicago
$313 Roundtrip, found 1 hour ago
$313
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Jun 16 from Fort Myers to Chicago, returning Thu, Jun 18, priced at $313 found 1 hour ago
Delta
Thu, Nov 26 - Tue, Dec 1
RSW
Fort Myers
ORD
Chicago
$315 Roundtrip, just found
$315
Roundtrip
just found
Select Delta flight, departing Thu, Nov 26 from Fort Myers to Chicago, returning Tue, Dec 1, priced at $315 just found
Southwest Airlines
Sat, May 30 - Tue, Jun 9
RSW
Fort Myers
ORD
Chicago
$316 Roundtrip, found 1 day ago
$316
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, May 30 from Fort Myers to Chicago, returning Tue, Jun 9, priced at $316 found 1 day ago
Sun Country Airlines
Wed, Jul 29 - Mon, Aug 3
RSW
Fort Myers
ORD
Chicago
$319 Roundtrip, just found
$319
Roundtrip
just found
Select Sun Country Airlines flight, departing Wed, Jul 29 from Fort Myers to Chicago, returning Mon, Aug 3, priced at $319 just found

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $444
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $444

Frequently asked questions

How much does a flight from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $135 and cheap return flights from $295 Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights typically cost between $122 and $740, and return flights often range between $242 and $1052. 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 Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The cheapest month to fly from RSW to ORD is June 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're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
4 airlines operate nonstop service from RSW to ORD:

  • United operates around 52 direct flights from RSW to ORD every week
  • American Airlines operates around 27 direct flights from RSW to ORD every week
  • Spirit Airlines operates around 17 direct flights from RSW to ORD every week
  • Frontier Airlines operates around 8 direct flights from RSW to ORD every week

How do I find cheap flights from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.), 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 airline to fly with from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Fort Myers, FL (RSW) to Chicago, IL (ORD) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, Frontier Airlines typically offers the lowest fares. American Airlines offers the most daily flights from RSW to ORD, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare 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.
How many flights per day from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 13 nonstop flights per day from Southwest Florida Intl. (RSW) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Fort Myers, FL (RSW - Southwest Florida Intl.) to Chicago, IL (ORD - O'Hare Intl.) typically departs at around 5:00 AM, operated by Southwest Airlines. This seasonal service is available in April, May, and June, allowing you to start your day early in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Fort Myers, FL (RSW) to Chicago, IL (ORD) are in the early morning, from 6am to 9am. About 27% of passengers prefer this time window. Many major carriers, including American Airlines and Delta, offer flights during this window. This timing works well because it allows you to arrive in Chicago with plenty of time to enjoy the day ahead.
How long does it take to fly from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Direct flights from RSW to ORD usually take about 3 hours 20 minutes, traveling roughly 1,123 miles. If you opt for a connecting flight, expect to add around 3 hours 40 minutes to your journey. 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 Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
First class seats are offered on the RSW to ORD route. First class cabins are available on:

  • American Airlines
  • United Airlines
  • Delta Air Lines
  • Spirit Airlines

How much is a business class flight from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A direct, return business class ticket from Fort Myers, FL (RSW) to Chicago, IL (ORD) typically costs between $1,214 - $1,895. A non-stop, one-way business class flight is usually around $656 - $976. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.) 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.
What airports do you fly into for Chicago from Southwest Florida Intl. (RSW)?
When traveling from Southwest Florida Intl. (RSW) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like Charlotte-Douglas Intl. (CLT), Hartsfield-Jackson Atlanta Intl. (ATL), Liberty Intl. (EWR) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.) 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 Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages 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 Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Fort Myers, FL (RSW-Southwest Florida Intl.) to Chicago, IL (ORD-O'Hare Intl.) 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
Southwest Florida Intl.
Destination airport
O'Hare Intl.
Roundtrip price
$295
Distance
1122 mi
Average flight time
2 hours 20 mins

Book with confidence

Fort Myers to Chicago Flights

The cheapest times to fly from Fort Myers to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Fort Myers to Chicago are during the month of June. You can find some of the cheapest flights from Fort Myers to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Fort Myers to Chicago

Sunday is one of the best days to book for cheap flights from Fort Myers to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Fort Myers to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Fort Myers to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $135 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Fort Myers to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Fort Myers to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Fort Myers to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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