CHO - CHI

$209 Find Cheap Flights from Charlottesville to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Charlottesville to Chicago departing on 1/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Charlottesville to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Charlottesville to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$209
Overall average: $353
United Airlines
Thu 1/29Sat 1/31
CHO - ORD • Non-stop
Cheapest one-way
$224
Overall average: $258
United Airlines
Wed 1/21
CHO - ORD • Non-stop
Top airlines
United Airlines
Cheapest • from $209 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
CHO-ORD
Cheapest
CHO-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
5 weeks
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 38% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 28% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Charlottesville to Chicago (CHO-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Charlottesville to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Charlottesville to Chicago

Thu, Jan 29 - Sat, Jan 31
United Airlines Logo
2:17 pm - 3:33 pm
CHO
-
ORD
2h 16mnonstop
United Airlines Logo
1:55 pm - 5:02 pm
ORD
-
CHO
2h 07mnonstop
$209United Airlines
Thu, Jan 29 - Sun, Feb 1
United Airlines Logo
2:41 pm - 6:37 pm
CHO
-
ORD
4h 56m1 stop
United Airlines Logo
10:35 am - 1:42 pm
ORD
-
CHO
2h 07mnonstop
$219United Airlines
Thu, Feb 19 - Mon, Feb 23
United Airlines Logo
6:45 am - 7:57 am
CHO
-
ORD
2h 12mnonstop
United Airlines Logo
5:45 pm - 8:42 pm
ORD
-
CHO
1h 57mnonstop
$222United Airlines
Thu, Jan 29 - Sat, Jan 31
Delta Logo
6:00 am - 9:53 am
CHO
-
MDW
4h 53m1 stop
Delta Logo
6:25 am - 2:48 pm
MDW
-
CHO
7h 23m1 stop
$229Delta
Thu, Jan 29 - Sat, Jan 31
Delta Logo
5:30 pm - 11:56 pm
CHO
-
ORD
7h 26m1 stop
Delta Logo
11:20 am - 6:50 pm
ORD
-
CHO
6h 30m1 stop
$229Delta
Wed, Mar 4 - Mon, Mar 9
American Airlines Logo
4:44 pm - 10:20 pm
CHO
-
ORD
6h 36m1 stop
American Airlines Logo
8:10 am - 3:59 pm
ORD
-
CHO
6h 49m1 stop
$244American Airlines
Thu, Jan 1 - Mon, Jan 5
United Airlines Logo
10:50 am - 12:05 pm
CHO
-
ORD
2h 15mnonstop
United Airlines Logo
5:50 pm - 8:57 pm
ORD
-
CHO
2h 07mnonstop
$249United Airlines
Thu, Apr 23 - Mon, Apr 27
American Airlines Logo
8:14 pm - 11:50 pm
CHO
-
ORD
4h 36m1 stop
American Airlines Logo
6:16 am - 1:31 pm
ORD
-
CHO
6h 15m1 stop
$259American Airlines
Thu, Apr 23 - Mon, Apr 27
United Airlines Logo
7:00 am - 8:11 am
CHO
-
ORD
2h 11mnonstop
United Airlines Logo
7:15 am - 10:11 am
ORD
-
CHO
1h 56mnonstop
$264United Airlines
Thu, Feb 19 - Mon, Feb 23
Delta Logo
5:28 pm - 10:42 pm
CHO
-
MDW
6h 14m1 stop
Delta Logo
6:00 am - 1:58 pm
MDW
-
CHO
6h 58m1 stop
$369Delta
Booking Insights

KAYAK's insights & trends for Charlottesville to Chicago flights

Get data-powered insights and trends into flights from Charlottesville to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Charlottesville to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Charlottesville to Chicago costs $239 on the route between Charlottesville (CHO) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

What’s the cheapest day of the week to fly from Charlottesville to Chicago?

The average price of all round-trip flights from Charlottesville to Chicago clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Charlottesville to Chicago. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Charlottesville to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Charlottesville to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Charlottesville to Chicago is January, where tickets cost $279 (return) on average. On the other hand, the most expensive months are September and June, where the average cost of round-trip tickets is $544 and $498 respectively.

Can I save money by flying with a layover from Charlottesville to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $358, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Charlottesville to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Charlottesville to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Charlottesville to Chicago, you should book around 5 weeks before departure, which saves you about 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonDecember
Cheapest flight$209
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Charlottesville to Chicago O'Hare Airport

When to book flights from Charlottesville to Chicago

Are your dates flexible? Find out the best times to travel from Charlottesville to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Charlottesville to Chicago

  • What is the cheapest flight from Charlottesville to Chicago?

    In the last 3 days, the lowest price for a flight from Charlottesville to Chicago was $224 for a one-way ticket and $209 for a round-trip.

  • Do I need a passport to fly between Charlottesville and Chicago?

    No, a passport isn't needed to fly from Charlottesville to Chicago. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Charlottesville to Chicago?

    When flying out of Charlottesville you will be using Charlottesville Albemarle. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Charlottesville to Chicago?

    All the following airlines offer inflight Wi-Fi service on the Charlottesville to Chicago flight route: Lufthansa, United Airlines, American Airlines, Alaska Airlines, Delta, and Hawaiian Airlines.

  • Which aircraft models fly most regularly from Charlottesville to Chicago?

    The Canadair (Bombardier) Regional Jet CRJ-550 is the aircraft model that flies most regularly on the Charlottesville to Chicago flight route.

  • Which airline alliances offer flights from Charlottesville to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Charlottesville and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Charlottesville to Chicago?

    There are nonstop flights from Charlottesville to Chicago on a daily basis.

  • Which is the best airline for flights from Charlottesville to Chicago, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Charlottesville to Chicago are United Airlines and American Airlines. With an average price for the route of $386 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $273 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Charlottesville to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Charlottesville to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Charlottesville to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Charlottesville is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Charlottesville to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Charlottesville with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Charlottesville to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Charlottesville up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Charlottesville to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $259 or less one-way and $352 or less round-trip.

Prefer to fly direct from Charlottesville to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Charlottesville Albemarle to Chicago.
Find which airlines fly direct from Charlottesville Albemarle Airport to Chicago, which days they fly and book direct flights.

Direct departures

Charlottesville Albemarle to Chicago

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago to Charlottesville Albemarle

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the top airlines flying from Charlottesville to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Charlottesville to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Charlottesville to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9091 reviews
8.1Crew
7.1Entertainment
7.3Comfort
7.7Boarding
6.6Food
Airline reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

10.0 ExcellentRoger, Dec 2025
CAE - ORD
Read more United Airlines reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Everything you need to know for your flight from Charlottesville to Chicago

Information on your arrival and departure airports