Cheap Flights from Charlottesville to Chicago

Compare Charlottesville to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Find the cheapest month to fly from Charlottesville to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Charlottesville to Chicago flights are currently cheapest in April.

Direct flights from Charlottesville to Chicago

Charlottesville to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 4,421
Cheapest month to flyApril
Average flight time2 hrs, 10 mins
Most popular airlineUnited
Average flights per week85

Finding cheap flights from Charlottesville to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Charlottesville to Chicago is R 2,796. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 10 minutes is the average flight time from Charlottesville to Chicago.
United, SkyWest Airlines and Air New Zealand fly direct from Charlottesville to Chicago.
As of February 2026, there are 85 flights per week flying from Charlottesville to Chicago.
The cheapest month to fly from Charlottesville to Chicago is usually June.
If you're flying from Charlottesville Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from R 2,796.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Charlottesville Airport to Chicago on Tuesday, 30 June 2026.
Yes – the average flight time is 2 hours and 10 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In February, the average temperature is usually around -2°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Delta and United offer the cheapest flight tickets to Chicago.

Travelling from Charlottesville Albemarle Airport (CHO) to Chicago: what you need to know

  • The average length of a direct flight from Charlottesville Albemarle Airport to Chicago is 2 hours.

  • Charlottesville Albemarle Airport is located in Charlottesville. Following the UTC-5 timezone, Chicago is one hour behind Charlottesville.

  • Charlottesville Albemarle Airport (CHO) to O'Hare International Airport (ORD) is the most traveled route, with 16 weekly departures to pick from. If you have things to finalize before heading off, the last flight from CHO to ORD is with United Airlines at 17:50. Go for the first departure operated by United Airlines at 06:45 if you want to fly out earlier.

  • Leave plenty of time to catch your CHO to Chicago flight. As a general rule, arrive at least two hours before international departures and an hour ahead for domestic flights.

  • Heading off during a peak period like school or public holidays? Expect longer queues at security and check-in. To play it safe, arrive up to four hours before international flights and two hours before domestic departures.

  • Begin your trip at CHO and fly straight to O'Hare International Airport (ORD). That will be your arrival point when searching for Charlottesville Albemarle Airport to Chicago tickets.

  • Book your favourite seat with United Airlines. This well-known airline offers direct flights from Charlottesville Albemarle Airport to Chicago.

  • The journey from central Charlottesville to CHO takes around 1 hour 5 minutes on public transport. If you ride-share, drive or take a cab, you'll cover the 13 kilometres in 20 minutes or so, depending on traffic conditions.

  • Want a hassle-free start to your journey? Stay near CHO. Whether you're boarding an early flight from Charlottesville Albemarle Airport to Chicago or don't want departure day to feel hectic, these hotels are a convenient choice:

  • Charlottesville Albemarle Airport maintains a solid on-time record, so you're less likely to experience disruptions. Departures from CHO arrive at their destination as scheduled 80.42% of the time.

  • You'll find CHO at 100 Bowen Loop.

How to find the cheapest flights from Charlottesville Albemarle Airport (CHO) to Chicago

  • The lowest price we've seen for a one-way Charlottesville Albemarle Airport to Chicago flight is R 4,421. The cheapest price for a return flight is R 2,796. Keep in mind fares can change due to availability at the time of booking.

  • To score cheap flights from CHO to Chicago, reserve your journey three months before your departure date.

  • The best month for picking up cheap Charlottesville Albemarle Airport to Chicago tickets is July. Use the 'Whole month' tool to compare all available prices, then choose the dates that offer the lowest fares.

  • Save time searching for cheap flights from CHO to Chicago by setting up a Price Alert. We'll send you an email or notification on the app when a new low fare is offered.

  • Tailor your trip with filters. Choose your arrival and departure times, airlines and total journey duration. You can also sort your results by 'Fastest,' 'Best' or 'Cheapest' flights from Charlottesville Albemarle Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is around 40 kilometres from central Chicago. If you're opting for a ride-share or a cab, the drive takes about 35 minutes.

  • Travelling on public transport will take you around 55 minutes.

  • If you're arriving on a late flight from Charlottesville Albemarle Airport to Chicago, few things beat the convenience of staying close to the terminal. Pick up your bags from the carousel and then be showered and sleeping soon after at one of these accommodation options near ORD:

  • Grab an O'Hare International Airport rental car and discover Chicago and beyond with your own set of wheels. Routes Car Rentals, Dollar and Budget are popular outlets to choose from here.

  • Reserving your vehicle from O'Hare International Airport around four weeks ahead of your flight from CHO to Chicago can help you lock in the best possible rate.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Once your flight from Charlottesville Albemarle Airport to Chicago has arrived, you can make your way to the city centre in around 20 minutes by car. Central Chicago is roughly 19 kilometres from Chicago Midway International Airport (MDW).

  • The trip will take about 45 minutes on public transport.

  • There are some comfortable places to park your luggage (and yourself) near MDW. Settle in and get cosy after your CHO to Chicago flight at any of these well-located options:

  • Dollar, Hertz and Budget make picking up a Chicago Midway International Airport rental car quick and easy. These suppliers are located in or around the terminal and will get you on your way in no time.

  • Get first dibs on the best options. Booking your ride from MDW four weeks ahead of time often means more savings and a greater range of vehicles.

  • Chicago Midway International Airport is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Hop off your flight from Charlottesville Albemarle Airport to Chicago and make your way to your hotel or start sightseeing right away. The centre of Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 25 minutes to reach driving.

  • Public transport can take you there in about 4 hours 15 minutes.

  • If you don't want to travel to the centre, choose a hotel near RFD. Check in to one of these options after your CHO to Chicago flight:

  • Take control of the next leg of your trip by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National are some companies you can book with.

  • Booking a couple of weeks in advance of your flight from Charlottesville Albemarle Airport to Chicago is a smart move. Along with better deals, you'll be able to choose the vehicle make and model you prefer at RFD.

  • The address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your trip dates before booking your flight from Charlottesville Albemarle Airport to Chicago. The city comes alive during high season, but hotel rates are often higher and major attractions can be crowded. Go to Chicago in the off-season for a more relaxed vibe.

  • Before booking a Charlottesville Albemarle Airport to Chicago flight ticket, think about what kind of weather works for you. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • Look for cheap tickets from CHO to Chicago in January if you'd rather travel when it's cooler. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

Explore more of United States

  • Columbus is just one of the many cities in United States waiting to be explored once you've taken in the sights of Chicago. Around 451 kilometres away to the south-east, well-known attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • If you're ready to explore another side of United States, head for Indianapolis, roughly 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are among its highlights.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.