$199 Find Cheap Flights from Charlottesville to Chicago - Compare and Save

Among airlines operating Charlottesville to Chicago flights:

• United Airlines: offers extra legroom; offers free seat selection
• American Airlines: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

2 airlines operate flights between Charlottesville and Chicago. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines

Flights from Charlottesville to Chicago usually depart from Charlottesville Albemarle (CHO) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

Here are some options for this route, based on selected ticket types and cabin classes:

• United Airlines: a cabin bag and a checked bag in Economy Class
• American Airlines: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Two cabin classes are available on flights from Charlottesville to Chicago:

• Economy Class
• First Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $340 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $390 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Connecting flights from Charlottesville to Chicago most commonly pass through:

• Charlotte Douglas (CLT) - 69% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 31% of one-stop connections
Together, these airports account for 100% of one-stop bookings on this route.

Yes. Being flexible with your travel dates can save you up to 59% on the Charlottesville to Chicago route. Wednesday is the cheapest departure day at $307 round-trip on average, while Sunday is the most expensive at $737, a difference of $430. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Morning is the busiest departure period on Charlottesville to Chicago flights, with 50% of flights leaving in that window. Afternoon departures account for 25%, evening flights for 25%, and night flights for 0%.

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

These are the earliest and latest flight times available from Charlottesville to Chicago:

• Earliest: departs at 6:00 am and lands at 8:10 am
• Latest: departs at 6:48 pm and lands at 8:58 pm.

The flight takes about 2h 10m.

Last-minute fares on this route - booked within 2 weeks of departure - run 29% above the route average of $389. Book 23 weeks before departure for the lowest fares.

A nonstop flight from Charlottesville to Chicago takes 2h 10m, covering 549 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $299 to $1,752. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Charlottesville to Chicago are currently lower than usual. Average one-way flight prices are about $246, which is 24% below the typical average for this route.

Flying via Charlotte Douglas (CLT) gives the shortest average 1-stop total travel time at 4h 56m, compared with 5h 11m via Atlanta Hartsfield-Jackson (ATL).

Chicago is 1 hour behind Charlottesville (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Dollar
• Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Round-trip flights from Charlottesville to Chicago range from $300 to $504, with an average of $389 over the past 12 months. Anything below $300 counts as a good deal.

American Airlines is the only airline on the Charlottesville to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.