$58 Cheap Flights from Chicago (ORD) to Fort Myers (RSW)

View $58 flight on Thu, May 29, 2025Opens in a new window

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Find available prices by choosing your travel dates.

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

Prices were available within the past 7 days and start at $58 for one-way flights and $134 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Oct 21 - Tue, Oct 28
ORD
Chicago
RSW
Fort Myers
$134 Roundtrip, just found
$134
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Oct 21 from Chicago to Fort Myers, returning Tue, Oct 28, priced at $134 just found
Spirit Airlines
Wed, Aug 27 - Sat, Sep 6
ORD
Chicago
RSW
Fort Myers
$140 Roundtrip, found 4 days ago
$140
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Aug 27 from Chicago to Fort Myers, returning Sat, Sep 6, priced at $140 found 4 days ago
Spirit Airlines
Thu, May 29 - Mon, Jun 2
ORD
Chicago
RSW
Fort Myers
$145 Roundtrip, just found
$145
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 29 from Chicago to Fort Myers, returning Mon, Jun 2, priced at $145 just found
Spirit Airlines
Mon, May 19 - Sun, May 25
ORD
Chicago
RSW
Fort Myers
$148 Roundtrip, found 2 hours ago
$148
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Mon, May 19 from Chicago to Fort Myers, returning Sun, May 25, priced at $148 found 2 hours ago
Spirit Airlines
Thu, May 22 - Sun, May 25
ORD
Chicago
RSW
Fort Myers
$154 Roundtrip, just found
$154
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 22 from Chicago to Fort Myers, returning Sun, May 25, priced at $154 just found
Spirit Airlines
Thu, May 22 - Sun, May 25
ORD
Chicago
RSW
Fort Myers
$157 Roundtrip, just found
$157
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 22 from Chicago to Fort Myers, returning Sun, May 25, priced at $157 just found
Southwest Airlines
Sat, Jul 5 - Fri, Jul 11
ORD
Chicago
RSW
Fort Myers
$167 Roundtrip, found 9 hours ago
$167
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Sat, Jul 5 from Chicago to Fort Myers, returning Fri, Jul 11, priced at $167 found 9 hours ago
Delta
Tue, Jul 1 - Fri, Jul 11
ORD
Chicago
RSW
Fort Myers
$176 Roundtrip, just found
$176
Roundtrip
just found
Select Delta flight, departing Tue, Jul 1 from Chicago to Fort Myers, returning Fri, Jul 11, priced at $176 just found
American Airlines
Sat, Aug 30 - Sun, Sep 7
ORD
Chicago
RSW
Fort Myers
$179 Roundtrip, found 13 hours ago
$179
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Aug 30 from Chicago to Fort Myers, returning Sun, Sep 7, priced at $179 found 13 hours ago
United
Sat, Aug 30 - Sun, Sep 7
ORD
Chicago
RSW
Fort Myers
$179 Roundtrip, found 13 hours ago
$179
Roundtrip
found 13 hours ago
Select United flight, departing Sat, Aug 30 from Chicago to Fort Myers, returning Sun, Sep 7, priced at $179 found 13 hours ago

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) cost?
Cheap round-trip flights from O’Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) start at $130. 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 ORD on May 16 2025 and touching down at RSW. The price was last updated on April 22 2025 and has not changed since.
What is the cheapest month to fly from ORD to RSW?
The cheapest flights from ORD to RSW 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 O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
You can pick from 4 airlines that fly direct from O’Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW). Including:

  • United Airlines
  • American Airlines
  • Spirit Airlines

What is the cheapest airline that flies from ORD to RSW?
With prices starting from $65 for a one-way journey from ORD to RSW, Spirit Airlines is currently the cheapest carrier for this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on July 18 2025. Prices were last updated on April 22 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
When flying out of O’Hare Intl. Airport (ORD), you can take your pick from an average of 8 daily direct flights to Southwest Florida Intl. Airport (RSW).
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
Flights between ORD and RSW are busiest at 8 AM. If you’re after a less crowded experience and potentially cheaper tickets, look for a time when demand is lower.
What day of the week has the most flights from ORD to RSW?
Sunday offers the most flights from O’Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW). Consider jetting off on this day and you’ll have a greater chance of finding a schedule that works for you.
What is the earliest flight from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
The earliest flight taking off from O’Hare Intl. Airport (ORD) is at around 5:35AM UTC-6. Hop on this flight and you’ll land at Southwest Florida Intl. Airport (RSW) at approximately 9:29AM UTC-5. The overall travel time is 2h 54m.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
Typically, it takes 3 hours to cover the 1,100 mi from ORD to RSW.
What airline has the least delays from ORD to RSW?
Consider traveling with Frontier Airlines if you’d like to fly straight from O’Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) without any delays. This airline has the best track record for punctuality, with an on-time performance of 100%. Want to be notified if anything changes? You can check your flight status using the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
To avoid potential delays on the O’Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) route, travel before 3 PM. Later flights have a 22% higher chance of being 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 Fort Myers from O'Hare Intl. Airport (ORD)?
If you’re traveling on a direct flight from O’Hare Intl. Airport (ORD) to Fort Myers, Southwest Florida Intl. Airport (RSW) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) last-minute?
Waiting until just before your departure to book a flight from ORD to RSW generally means paying more. Although you may find some last-minute discounts, they aren’t always guaranteed. Allow some flexibility in your schedule for a better chance of getting a bargain.
Is it cheaper to book an ORD to RSW flight and hotel package?
Securing an ORD to RSW flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Select from our extensive range of hotels and then add flights, car rentals and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
If you booked your ORD to RSW flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you want more information.
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