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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Flight deals from Charlottesville to Chicago

Looking for a cheap last-minute deal or the best return flight from Charlottesville Airport to Chicago? If you want to travel next month, return fares start from $359. Find the lowest prices on one-way and return tickets right here.

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 June.

Direct flights from Charlottesville to Chicago

Charlottesville to Chicago: Flight information

The things to know before you go.
Cheapest flight found$324
Cheapest month to flyJune
Average flight time2 hrs, 8 mins
Most popular airlineUnited
Average flights per week222

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 $344. 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 8 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 June 2026, there are 74 flights per week flying from Charlottesville to Chicago.
The cheapest month to fly from Charlottesville to Chicago is usually October.
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 $344.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Charlottesville Airport to Chicago on Wednesday, 28 October 2026.
Yes – the average flight time is 2 hours and 8 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 June, the average temperature is usually around 19°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, United offers the cheapest flight tickets to Chicago.

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

  • Expect to be in the air for 2 hours. That's the average time for a direct flight from Charlottesville Albemarle Airport to Chicago.

  • Chicago is one hour behind Charlottesville, where Charlottesville Albemarle Airport is located. Chicago runs on the UTC-6 timezone.

  • Charlottesville Albemarle Airport (CHO) to Chicago O'Hare International Airport (ORD) is the most popular route, with 23 flights a week to pick from. If you have things to do before heading off, the last flight from CHO to ORD is with United Airlines at 17:50. Choose the first departure with United Airlines at 06:45 if you want to fly out earlier.

  • For hassle-free travel, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This leaves you with plenty of time to board your CHO to Chicago flight.

  • During popular months such as November, it's wise to get to the airport even earlier. Arrive two hours before domestic departures and four hours ahead for international flights whenever you're travelling during a peak period in general.

  • You can book a direct Charlottesville Albemarle Airport to Chicago ticket. Start your journey at CHO and end it at Chicago O'Hare International Airport (ORD).

  • Book your ticket with United Airlines. This popular carrier offers direct flights from Charlottesville Albemarle Airport to Chicago.

  • The journey from central Charlottesville to CHO takes about 35 minutes on public transport. If you drive, ride-share or grab a taxi, you'll cover the 13 kilometres in 15 minutes or so, depending on traffic conditions.

  • Want a relaxed start to your trip? Stay near CHO. Whether you're catching an early flight from Charlottesville Albemarle Airport to Chicago or want to avoid feeling rushed, these hotels have you covered:

  • When it comes to Charlottesville Albemarle Airport's on-time performance, 79% of flights arrive within the expected time frame.

  • The address for CHO is 100 Bowen Loop.

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

  • $324 is the cheapest price we've found for a one-way Charlottesville Albemarle Airport to Chicago flight. A round-trip ticket right now is $344. Depending on when you want to go and the availability, these fares may change.

  • To secure cheap flights from CHO to Chicago, reserve your trip two months before your planned departure.

  • Plan your trip for July. That's the best month for scoring the biggest deals on Charlottesville Albemarle Airport to Chicago tickets. If you're flexible with your dates, use the 'Whole month' tool to find the lowest price across every month.

  • Never miss a deal on cheap flights from CHO to Chicago by creating a Price Alert. You'll get an email or notification through the app when a new discounted fare appears.

  • Find an affordable flight from Charlottesville Albemarle Airport to Chicago with the help of our filters. Choose your preferred duration, departure time and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) to the centre of Chicago takes about 30 minutes by car. The centre is roughly 27 kilometres away.

  • It takes around 45 minutes to get there by public transport.

  • 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. Grab your suitcases from the carousel and then be showered and sleeping soon after at one of these hotels near ORD:

  • Get the best deal by reserving your vehicle from Chicago O'Hare International Airport about four weeks before your flight from CHO to Chicago.

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

Chicago Midway International Airport (MDW)

  • After your flight from Charlottesville Albemarle Airport to Chicago has arrived, you can make your way to the city centre in around 25 minutes by car. Central Chicago is roughly 16 kilometres from Chicago Midway International Airport (MDW).

  • The journey will take about 30 minutes on public transport.

  • After stepping off your CHO to Chicago flight, tuck yourself in at a hotel close to MDW. These are some comfortable options that'll help you get into relaxation mode:

  • Get what you want, not just what's left over. Securing your ride from MDW four weeks ahead of time often means better deals and a wider range of vehicles.

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

Chicago Rockford International Airport (RFD)

  • Make your way to the city centre after your flight from Charlottesville Albemarle Airport to Chicago has landed. Central Chicago is about 145 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 40 minutes to reach by car.

  • Public transport can get you there in around 2 hours.

  • If you don't want to make the trip into the centre, find a hotel near RFD. Get comfortable at one of these options after your CHO to Chicago flight:

  • Booking a couple of weeks in advance of your flight from Charlottesville Albemarle Airport to Chicago is a good move. As well as better deals, you'll have a wider selection of vehicle makes and models at RFD.

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

Best time to go to Chicago

  • July is the busiest month for flights from Charlottesville Albemarle Airport to Chicago. To skip the crowds, plan your trip to Chicago in January.

  • Lock in a Charlottesville Albemarle Airport to Chicago plane ticket with a departure in July if you want to experience the city during its warmest month. You can expect temperatures to range from 16ºC (61ºF) to 28ºC (82ºF).

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for a cheap ticket from CHO to Chicago around that time if you want to travel when it's cooler.

More about Chicago

  • After booking your flight from Charlottesville Albemarle Airport to Chicago, choose a hotel that puts you right where the action is. Make one of these accommodation options your base for exploring Chicago:

  • There are so many things to do and see in this city it can be hard to know where to begin. Art Institute of Chicago, Millennium Park and Willis Tower are top attractions which should be on every Chicago itinerary.

Explore more of the United States

  • Columbus is just one of the many places in the United States waiting to be explored once you've seen Chicago. Around 451 kilometres away to the southeast, check out popular attractions including Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Indianapolis is another favourite destination in the United States and is around 257 kilometres southeast of Chicago. No trip is complete without seeing Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.