Cheap flights from Charlottesville to Chicago from $189

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Charlottesville averaging around $379.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as $430. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Charlottesville because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $737.

Flying to Chicago O'Hare Intl Airport from Charlottesville at noon is the least expensive time of day to depart. momondo users have found prices as low as $405 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $494. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Charlottesville Albemarle to Chicago O'Hare Intl for the best Charlottesville Albemarle - Chicago O'Hare Intl flight prices

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Charlottesville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $417 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Charlottesville for as low as $209 on momondo.

There are 4 cabin classes available to choose from on Charlottesville to Chicago O'Hare Intl Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 10% on your flight if you consider stops on a Charlottesville to Chicago O'Hare Intl Airport flight.

As of August 2026, prices for Charlottesville to Chicago O'Hare Intl Airport flights are approximately 8% cheaper when compared to flights at the same time last year.

United Airlines and Delta are the most popular carriers operating from Charlottesville Albemarle to Chicago O'Hare Intl

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Charlottesville according to our data. United Airlines is the first choice among our users, with 63% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 6 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

Atlanta (ATL) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Atlanta (ATL) offer the lowest average round-trip price of $187.

Flights connecting via Charlotte (CLT) have the shortest average one-way travel time: 5h 01m.

Atlanta (ATL) has the shortest average layover time for this route: 1h 30m.

5 flights are operational daily from Charlottesville to Chicago O'Hare Intl Airport as of August 2026. The most popular departure time for this route is 6:00AM, with 60% of flights per day taking off at noon.

As of August 2026, there are 35 flights per week flying from Charlottesville to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.