CHO - CHI

$134 Find Cheap Flights from Charlottesville to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Charlottesville to Chicago departing on 10/18. 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

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
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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

Wed, Dec 3 - Sun, Dec 7
United Airlines Logo
2:09 pm - 3:21 pmCHO-ORD
2h 12mnonstop
United Airlines Logo
7:20 am - 10:15 amORD-CHO
1h 55mnonstop
$209United Airlines
Find Deal
Wed, Dec 3 - Sat, Dec 6
United Airlines Logo
10:35 am - 2:25 pmCHO-ORD
4h 50m1 stop
United Airlines Logo
7:20 am - 10:15 amORD-CHO
1h 55mnonstop
$219United Airlines
Find Deal
Sat, Oct 18 - Wed, Oct 22
United Airlines Logo
7:00 am - 8:05 amCHO-ORD
2h 05mnonstop
United Airlines Logo
7:49 am - 10:48 amORD-CHO
1h 59mnonstop
$227United Airlines
Find Deal
Thu, Oct 16 - Tue, Oct 21
Delta Logo
5:35 am - 9:40 amCHO-MDW
5h 05m1 stop
Delta Logo
6:00 am - 11:11 amMDW-CHO
4h 11m1 stop
$229Delta
Find Deal
Sat, Oct 4 - Wed, Oct 8
United Airlines Logo
12:38 pm - 1:47 pmCHO-ORD
2h 09mnonstop
United Airlines Logo
8:50 am - 1:53 pmORD-CHO
4h 03m1 stop
$229United Airlines
Find Deal
Sat, Oct 4 - Tue, Oct 7
Delta Logo
11:55 am - 3:26 pmCHO-MDW
4h 31m1 stop
Delta Logo
6:00 am - 1:50 pmMDW-CHO
6h 50m1 stop
$239Delta
Find Deal
Sat, Oct 4 - Tue, Oct 7
Delta Logo
11:55 am - 4:31 pmCHO-ORD
5h 36m1 stop
Delta Logo
5:20 am - 11:11 amORD-CHO
4h 51m1 stop
$239Delta
Find Deal
Fri, Oct 3 - Sun, Oct 5
American Airlines Logo
6:51 pm - 11:12 pmCHO-ORD
5h 21m1 stop
American Airlines Logo
5:00 am - 10:48 amORD-CHO
4h 48m1 stop
$250American Airlines
Find Deal
Wed, Oct 15 - Mon, Oct 20
American Airlines Logo
1:58 pm - 8:39 pmCHO-ORD
7h 41m1 stop
American Airlines Logo
5:22 am - 10:31 amORD-CHO
4h 09m1 stop
$264American Airlines
Find Deal
Fri, Oct 17 - Mon, Oct 20
American Airlines Logo
7:57 pm - 11:53 pmCHO-ORD
4h 56m1 stop
American Airlines Logo
5:22 am - 10:31 amORD-CHO
4h 09m1 stop
$274American Airlines
Find Deal

Everything you should know

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
9 weeks
in advance
Our data shows that travelers who book at least 9 weeks in advance save around 48% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 30% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$209
Overall average: $374
United Airlines
Wed 12/3Sun 12/7
CHO - ORD • Non-stop
Cheapest non-stop
$209
Typical prices: $279-469
United Airlines
Wed 12/3Sat 12/6
CHO - ORD • Non-stop
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!
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 $259 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, Sunday 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 February, where tickets cost $281 (return) on average. On the other hand, the most expensive months are June and September, where the average cost of round-trip tickets is $503 and $488 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 $409, 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 9 weeks before departure, which saves you about 48% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$134
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 3% 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 $134 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?

    Alaska Airlines, American Airlines, Delta, and Hawaiian Airlines offer inflight Wi-Fi service on the Charlottesville to Chicago flight route.

  • 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?

    Star Alliance is the only airline alliance operating flights between Charlottesville and Chicago.

  • 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 $408 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 $242 or less one-way and $360 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 8929 reviews
6.6Food
7.3Comfort
7.1Entertainment
7.7Boarding
8.1Crew
Airline reviews

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

2.0 MediocreAnonymous, Aug 2025RSW - ORD
Read more United Airlines reviews

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

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.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

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

Information on your arrival and departure airports

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