$79 Cheap United flights Chicago (ORD) to Fort Myers (RSW)

View $79 flight on Sat, Aug 30, 2025Opens in a new window

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$79 Cheap United flights Chicago (ORD) to Fort Myers (RSW)

Prices were available within the past 7 days and start at $79 for one-way flights and $119 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sat, Aug 30 - Sun, Sep 7
ORD
Chicago
RSW
Fort Myers
$119 Roundtrip, just found
$119
Roundtrip
just found
Select United flight, departing Sat, Aug 30 from Chicago to Fort Myers, returning Sun, Sep 7, priced at $119 just found
United
Sun, Aug 31 - Thu, Sep 4
ORD
Chicago
RSW
Fort Myers
$120 Roundtrip, just found
$120
Roundtrip
just found
Select United flight, departing Sun, Aug 31 from Chicago to Fort Myers, returning Thu, Sep 4, priced at $120 just found
United
Tue, Oct 21 - Thu, Oct 23
ORD
Chicago
RSW
Fort Myers
$125 Roundtrip, just found
$125
Roundtrip
just found
Select United flight, departing Tue, Oct 21 from Chicago to Fort Myers, returning Thu, Oct 23, priced at $125 just found
United
Sat, Oct 25 - Mon, Oct 27
ORD
Chicago
RSW
Fort Myers
$129 Roundtrip, just found
$129
Roundtrip
just found
Select United flight, departing Sat, Oct 25 from Chicago to Fort Myers, returning Mon, Oct 27, priced at $129 just found
United
Mon, Sep 1 - Wed, Sep 3
ORD
Chicago
RSW
Fort Myers
$132 Roundtrip, just found
$132
Roundtrip
just found
Select United flight, departing Mon, Sep 1 from Chicago to Fort Myers, returning Wed, Sep 3, priced at $132 just found
United
Tue, Oct 21 - Mon, Oct 27
ORD
Chicago
RSW
Fort Myers
$135 Roundtrip, found 16 hours ago
$135
Roundtrip
found 16 hours ago
Select United flight, departing Tue, Oct 21 from Chicago to Fort Myers, returning Mon, Oct 27, priced at $135 found 16 hours ago
Flights from Chicago (ORD) to Fort Myers (RSW)
Origin airport
O'Hare Intl.
Destination airport
Southwest Florida Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United
Popular airline
JetBlue Airways
Distance
1122 mi

Frequently asked questions

How much is a United Airlines flight from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
Grab budget-friendly return United Airlines flights from $119 from ORD to RSW by sorting your results from "Price (lowest to highest)" on Expedia. Or look for deals from $79 for a one-way trip.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly from ORD to RSW with United Airlines?
August is one of the least expensive months to get away to Fort Myers with United Airlines. You could also find great deals on one-way and round-trip tickets in September.
What is the cheapest time to book flights from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) with United Airlines?
Look for cheap United Airlines flights from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) one to three months before your departure date. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. Regardless of fare type and journey, the best day to book a domestic flight is generally Sunday and the most expensive is typically Monday. Passengers who book on a Sunday can save 6% on average compared to those who book their travel on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.
Does United Airlines fly nonstop from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
Skip the layovers and fly from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) on any of United Airlines's 32 weekly direct flights. Make use of our "Nonstop" and "Airline" filters to find the United Airlines flight that'll get you to RSW at your preferred time.
How long does it take to fly from ORD to RSW with United Airlines?
It takes approximately 3h 5m to fly nonstop from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) with United Airlines.
Which day of the week has the most United Airlines flights from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
If it's flexibility you're after, Wednesday offers the most choice for United Airlines flights from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW). Take your pick of 5 different departures.
What is the earliest United Airlines flight from ORD to RSW?
Taking off from ORD at 7:15AM UTC-6, the earliest United Airlines flight to RSW lands at 11:21AM UTC-5. Traveling early means you'll be less likely to encounter delays.* Prefer to travel later? The last United Airlines flight from ORD to RSW departs at 4:15PM UTC-6 and touches down at 8:20PM UTC-5.*Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports does United Airlines fly into in Fort Myers?
Southwest Florida Intl. Airport (RSW) is the main Fort Myers hub for United Airlines flights from O'Hare Intl. Airport (ORD).
Why fly with United Airlines from ORD to RSW?
With a rewarding loyalty program, United Airlines is a top choice for many travelers departing from ORD to RSW. Plus, as a United Mileage Plus and One Key™ member booking through Expedia, you can earn OneKeyCash™* on eligible flights along with your airline miles.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
What type of plane does United Airlines fly from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
For the O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) route, United Airlines typically operates Boeing 737-800 and Airbus A321neo planes. Remember that last-minute changes can occur for operational purposes, meaning your flight may be on a different aircraft.
Can I change or cancel my United Airlines flight from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
It's usually possible to reschedule or cancel your flight, although additional fees may apply if you booked more than 24 hours ago. Need flexible options? Apply the "Changes included" and "No cancel fee" filters to find flights that won't penalize you if you need to alter your plans. To make modifications, visit "Trips," select your flight and click on "Manage Booking" for more information.

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