Cheap flights from Charlottesville to Chicago from $99

The month of November is, on average, the cheapest month to fly to Chicago from Charlottesville, with most prices found around $303. If you’re not able to fly to Chicago in November, then October is your next best option. Flight prices from Charlottesville to Chicago during October average around $330.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $427. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Charlottesville to Chicago for around $730.

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Charlottesville to Chicago during this time can be as low as $406. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $485.

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

You are more likely to see cheaper flights to Chicago from Charlottesville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $416 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Charlottesville for as low as $209 on momondo.

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

Delta, American Airlines, and United Airlines are the most popular carriers operating from Charlottesville Albemarle to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Charlottesville according to our data. United Airlines is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago 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.

The number of flights available between Charlottesville and Chicago is 5 per day as of August 2026. The most frequent departure time is 6:00AM, with 60% of daily flights leaving in the afternoon.

35 flights are operational weekly from Charlottesville to Chicago as of August 2026. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.