$32 Cheap Flights from Fort Myers (RSW) to Chicago (ORD)

View $32 flight on Wed, Aug 6, 2025Opens 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 $32 for one-way flights and $80 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed, Aug 6 - Thu, Aug 7
RSW
Fort Myers
ORD
Chicago
$80 Roundtrip, found 1 hour ago
$80
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Aug 6 from Fort Myers to Chicago, returning Thu, Aug 7, priced at $80 found 1 hour ago
Spirit Airlines
Fri, Oct 31 - Tue, Nov 4
RSW
Fort Myers
ORD
Chicago
$96 Roundtrip, found 1 hour ago
$96
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Fri, Oct 31 from Fort Myers to Chicago, returning Tue, Nov 4, priced at $96 found 1 hour ago
Spirit Airlines
Sun, Oct 5 - Mon, Oct 6
RSW
Fort Myers
ORD
Chicago
$101 Roundtrip, found 1 hour ago
$101
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sun, Oct 5 from Fort Myers to Chicago, returning Mon, Oct 6, priced at $101 found 1 hour ago
Spirit Airlines
Wed, Aug 6 - Sat, Aug 9
RSW
Fort Myers
ORD
Chicago
$110 Roundtrip, found 2 hours ago
$110
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, Aug 6 from Fort Myers to Chicago, returning Sat, Aug 9, priced at $110 found 2 hours ago
Spirit Airlines
Sat, Aug 30 - Sun, Aug 31
RSW
Fort Myers
ORD
Chicago
$121 Roundtrip, found 1 hour ago
$121
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Aug 30 from Fort Myers to Chicago, returning Sun, Aug 31, priced at $121 found 1 hour ago
Spirit Airlines
Sat, Aug 2 - Mon, Aug 4
RSW
Fort Myers
ORD
Chicago
$126 Roundtrip, found 2 hours ago
$126
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, Aug 2 from Fort Myers to Chicago, returning Mon, Aug 4, priced at $126 found 2 hours ago
American Airlines
Thu, Sep 4 - Mon, Sep 8
RSW
Fort Myers
ORD
Chicago
$128 Roundtrip, found 1 hour ago
$128
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Sep 4 from Fort Myers to Chicago, returning Mon, Sep 8, priced at $128 found 1 hour ago
United
Sat, Sep 13 - Sun, Sep 14
RSW
Fort Myers
ORD
Chicago
$134 Roundtrip, found 1 hour ago
$134
Roundtrip
found 1 hour ago
Select United flight, departing Sat, Sep 13 from Fort Myers to Chicago, returning Sun, Sep 14, priced at $134 found 1 hour ago
Southwest Airlines
Thu, Aug 7 - Mon, Aug 11
RSW
Fort Myers
ORD
Chicago
$137 Roundtrip, found 2 hours ago
$137
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Thu, Aug 7 from Fort Myers to Chicago, returning Mon, Aug 11, priced at $137 found 2 hours ago
JetBlue Airways
Fri, Sep 5 - Tue, Sep 9
RSW
Fort Myers
ORD
Chicago
$211 Roundtrip, found 2 hours ago
$211
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Fri, Sep 5 from Fort Myers to Chicago, returning Tue, Sep 9, priced at $211 found 2 hours ago

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

January is typically the cheapest month to fly

From $58 - $322 per traveler.

Graph displaying average flight prices per month

Flights from Fort Myers (RSW) to Chicago (ORD)
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
$79
Distance
1122 mi
Average flight time
2 hours 15 mins

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 August. 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 $32 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.

 

Frequently asked questions

How much does a flight from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD) cost?
Snag cheap return fares starting at $90 from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Spirit Airlines flight leaving RSW on August 4 2025 and touching down at ORD. The price was last updated on July 8 2025 and has not changed since.
What is the cheapest month to fly from RSW to ORD?
The cheapest flights from RSW to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 RSW to ORD?
Jet off from RSW to ORD with Spirit Airlines. This carrier currently has the cheapest one-way ticket on this route, starting from $45. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from RSW on October 3 2025. Prices were last updated on July 8 2025 and have not changed since.
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.

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