$99 Cheap United flights Jacksonville (JAX) to Chicago (ORD)

Landing cheap one-way United Airlines flights from JAX to ORD from $99 on Expedia is simple — just filter by “Price (lowest to highest).” Alternatively, check out our budget-friendly round-trip fares from $197 for your next exciting vacation.**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.

Browse for one-way or round-trip flights to Chicago in January or February. You could find lower fares with United Airlines during these off-peak travel months.

To find cheap United Airlines fares from Jacksonville Intl. Airport (JAX) to O’Hare Intl. Airport (ORD), start searching one to three months before your planned departure. Reserving domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also affect how much you pay. Sunday tends to be the most affordable, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your trip on a Sunday.**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.

Skip the layovers and fly from Jacksonville Intl. Airport (JAX) to O’Hare Intl. Airport (ORD) on any of United Airlines’s 20 direct weekly flights. Apply Expedia’s “Nonstop” and “Airline” filters to find the United Airlines flight that’ll take you to ORD at a time that suits you.

The journey time for a direct United Airlines flight from Jacksonville Intl. Airport (JAX) to O’Hare Intl. Airport (ORD) takes around 2h 47m.

If it’s flexibility you’re after, Thursday offers the most choice for United Airlines flights from Jacksonville Intl. Airport (JAX) to O’Hare Intl. Airport (ORD). You can select from 4 different departures.

The first flight from JAX to ORD with United Airlines leaves at 10:00AM UTC-5. You’ll touch down at 11:45AM UTC-6. The final United Airlines flight of the day leaves at 5:40PM UTC-5 and arrives at 7:10PM UTC-6. With 20% fewer cancellations for morning and mid-morning flights, starting your travel day early is often the best option.**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.

United Airlines flights from Jacksonville Intl. Airport (JAX) to Chicago arrive at O’Hare Intl. Airport (ORD) and Midway Intl. Airport (MDW). The main Chicago hub serviced by this airline is ORD. It’s worth comparing flights arriving at nearby airports on Expedia as they may have cheaper tickets.

Depart from JAX to ORD with United Airlines and you’ll enjoy a host of benefits including a rewarding loyalty program. When booking through Expedia as a United Mileage Plus and One Key™ member, you can also earn OneKeyCash™* to redeem on select future travel purchases.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

For the Jacksonville Intl. Airport (JAX) to O’Hare Intl. Airport (ORD) route, United Airlines typically operates Embraer 175 and Boeing 737-700 planes. Don’t forget that last-minute changes are possible for operational needs, meaning your flight may be on another aircraft.

Depending on the type of ticket you purchased, a fee is typically charged if you modify or cancel your booking 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. To learn more about changing or canceling your reservation, head to “Trips,” select your flight and click on “Manage Booking.”