$90 Cheap United flights Fort Myers (RSW) to Chicago (ORD)

Grab budget-friendly return United Airlines flights from $156 from RSW to ORD by sorting your results from “Price (lowest to highest)” on Expedia. Or search for options from $90 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.

United Airlines flights to Chicago are generally cheaper in the off-peak months of January and February. Whether you’re searching for a round-trip or one-way ticket, you could land a better deal then.

Search for cheap United Airlines flights from Southwest Florida Intl. Airport (RSW) to O’Hare Intl. Airport (ORD) one to three months prior to your departure day. 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 itinerary, the best day to book a domestic flight is usually Sunday and the most expensive day 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.

United Airlines operates direct flights from Southwest Florida Intl. Airport (RSW) to O’Hare Intl. Airport (ORD), with 32 departures each week. Just choose the “Nonstop” and “Airline” filters during your search on Expedia to see all direct United Airlines flights to ORD.

The journey time for a nonstop United Airlines flight from Southwest Florida Intl. Airport (RSW) to O’Hare Intl. Airport (ORD) takes around 3h 17m.

Thursday has the most United Airlines flights from Southwest Florida Intl. Airport (RSW) to O’Hare Intl. Airport (ORD). With 5 daily departures, this is a great day to find something that will work for your schedule.

Leaving RSW at 7:20AM UTC-5, the first United Airlines flight to ORD arrives at 9:37AM UTC-6. Traveling early means you’ll be less likely to encounter delays.* Not an early riser? The last United Airlines flight from RSW to ORD departs at 6:05PM UTC-5 and touches down at 8:22PM UTC-6.*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.

O’Hare Intl. Airport (ORD) is the main arrival point for United Airlines flights from Southwest Florida Intl. Airport (RSW) to Chicago. But this carrier also travels to Midway Intl. Airport (MDW). Make sure you check Expedia’s “All Airports” option for your destination to see exactly what’s available for your journey to Chicago.

A rewarding loyalty program and the ability to rack up points through United Mileage Plus are the start of the reasons to jet off from RSW to ORD with United Airlines. Plus, when you join Expedia’s free One Key™ program, you can receive OneKeyCash™* on top of any airline loyalty program earnings. It’s yours to spend on future bookings.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

For the Southwest Florida Intl. Airport (RSW) to O’Hare Intl. Airport (ORD) route, United Airlines typically operates Boeing 737-900 and Airbus A321neo planes. Keep in mind that last-minute changes are possible for operational purposes, so your flight may be on a different aircraft.

Depending on your ticket type, a fee will generally apply if you cancel or change your flight more than 24 hours after confirmation. To find tickets with more flexibility, select our “Changes included” and “No cancel fee” boxes when you search for flights. For additional information on canceling or changing your reservation, go to “Trips,” select your flight and tick “Manage Booking.”