$34 Cheap Flights from Fort Myers (RSW) to Chicago (ORD)

View $34 flight on Sat, Feb 28, 2026Opens in a new window

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

    notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
    deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
    trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

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

Prices were available within the past 7 days and start at $34 for one-way flights and $90 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Jan 31 - Sat, Feb 28
RSW
Fort Myers
ORD
Chicago
$90 Roundtrip, found 3 hours ago
$90
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Sat, Jan 31 from Fort Myers to Chicago, returning Sat, Feb 28, priced at $90 found 3 hours ago
Frontier Airlines
Sat, Feb 14 - Sat, Feb 21
RSW
Fort Myers
ORD
Chicago
$90 Roundtrip, just found
$90
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Feb 14 from Fort Myers to Chicago, returning Sat, Feb 21, priced at $90 just found
Spirit Airlines
Wed, Feb 25 - Sat, Feb 28
RSW
Fort Myers
ORD
Chicago
$91 Roundtrip, just found
$91
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Feb 25 from Fort Myers to Chicago, returning Sat, Feb 28, priced at $91 just found
Frontier Airlines
Sat, Feb 14 - Sat, Feb 21
RSW
Fort Myers
ORD
Chicago
$95 Roundtrip, just found
$95
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Feb 14 from Fort Myers to Chicago, returning Sat, Feb 21, priced at $95 just found
United
Thu, Jan 8 - Sat, Jan 10
RSW
Fort Myers
ORD
Chicago
$97 Roundtrip, found 15 hours ago
$97
Roundtrip
found 15 hours ago
Select United flight, departing Thu, Jan 8 from Fort Myers to Chicago, returning Sat, Jan 10, priced at $97 found 15 hours ago
Spirit Airlines
Fri, Oct 31 - Sun, Nov 16
RSW
Fort Myers
ORD
Chicago
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Oct 31 from Fort Myers to Chicago, returning Sun, Nov 16, priced at $100 found 1 day ago
Frontier Airlines
Sat, Jan 10 - Mon, Jan 19
RSW
Fort Myers
ORD
Chicago
$106 Roundtrip, just found
$106
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jan 10 from Fort Myers to Chicago, returning Mon, Jan 19, priced at $106 just found
United
Wed, Jan 7 - Sat, Jan 10
RSW
Fort Myers
ORD
Chicago
$107 Roundtrip, found 13 hours ago
$107
Roundtrip
found 13 hours ago
Select United flight, departing Wed, Jan 7 from Fort Myers to Chicago, returning Sat, Jan 10, priced at $107 found 13 hours ago
Spirit Airlines
Tue, Jan 6 - Sat, Jan 10
RSW
Fort Myers
ORD
Chicago
$109 Roundtrip, found 8 hours ago
$109
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Tue, Jan 6 from Fort Myers to Chicago, returning Sat, Jan 10, priced at $109 found 8 hours ago
Southwest Airlines
Sat, Feb 14 - Tue, Feb 17
RSW
Fort Myers
ORD
Chicago
$113 Roundtrip, found 5 hours ago
$113
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, Feb 14 from Fort Myers to Chicago, returning Tue, Feb 17, priced at $113 found 5 hours ago

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

February is typically the cheapest month to fly

From $68 - $240 per traveler.

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. Closest option available. Average driving time to city center is 16 minutes. Flights from $208
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $208

Frequently asked questions

How much does a flight from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $34 or cheap return flight from $90 from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD)?
Planning your getaway for January may help you find better deals, as it's the cheapest month for flights between RSW and ORD. You'll typically find the lowest prices during off-peak months.
Which airlines fly direct from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD)?
You can pick from 4 airlines that operate direct flights from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD). These include:

  • United Airlines
  • American Airlines
  • Spirit Airlines

What is the cheapest airline that flies from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD)?
The cheapest airline to offer flights between Southwest Florida Intl. Airport (RSW) and O'Hare Intl. Airport (ORD) will change depending on when you want to travel. Frontier Airlines and Spirit Airlines are just some good options offering reasonable prices. Use Expedia's search tool to compare airlines in one place and find the right RSW to ORD flight that fits your budget.
How many flights per day from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD)?
When jetting out of Southwest Florida Intl. Airport (RSW), you can take your pick from an average of 8 daily nonstop flights to O'Hare Intl. Airport (ORD).
What are the most popular departure times for flights from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD)?
Flights between RSW and ORD tend to be busiest at 12 PM. If you want a quieter experience and potentially cheaper prices, choose a time outside the usual busy windows.
What day of the week has the most flights from RSW to ORD?
Jet off on a Thursday if you're looking for the best choice of flights from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD)?
Hop on the earliest flight at around 7:20AM UTC-5, leaving from Southwest Florida Intl. Airport (RSW). You'll be flying for roughly 3h 17m, reaching O'Hare Intl. Airport (ORD) at approximately 9:37AM UTC-6.
How long does it take to fly from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD)?
The average flight duration from RSW to ORD is 3 hours and 13 minutes, covering a distance of 1,100 mi.
What airline has the least delays from RSW to ORD?
United Airlines has the best performance for on-time direct flights from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD), with an on-time score of 81%. Use the Expedia App to view your journey status before you leave and get real-time updates about any trip changes.
What is the best time to fly from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD)?
To avoid possible delays on the Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD) route, aim to fly before 3 PM. Departures after this time are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Southwest Florida Intl. Airport (RSW)?
Hop on a direct flight from Southwest Florida Intl. Airport (RSW) to Chicago and land at O'Hare Intl. Airport (ORD). An alternative point of entry into this city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD) last-minute?
Booking your ticket from RSW to ORD shortly before your journey is generally more expensive. However, if there's some wiggle room with your travel times and dates, you could bag a cheap last-minute fare.
Is it cheaper to book a RSW to ORD flight and hotel package?
You can save money by securing a RSW to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. After selecting your ideal flights and accommodations, consider adding extras such as tours, car rentals and activities.
Can I cancel or change the date of my flight from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD)?
In most cases, you're able to cancel or reschedule your RSW to ORD flight. However, additional fees may apply, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's policies and fees on flight changes, or if you want further details, visit our Customer Service portal.

Travel information

Origin airport
Southwest Florida Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United
Roundtrip price
$87
Distance
1122 mi
Average flight time
2 hours 11 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 January. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $34 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

Explore a world of travel with Expedia

*Available to One Key members.