CHO - CHI

$116 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 7/4. 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.
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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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Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Charlottesville to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Charlottesville to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
United Airlines Logo
7:59 pm - 11:30 pmCHO-ORD
4h 31m1 stop
United Airlines Logo
7:23 am - 10:25 amORD-CHO
2h 02mnonstop
$219United Airlines
Find Deal
Fri, May 23 - Mon, May 26
Delta Logo
5:43 pm - 9:27 pmCHO-MDW
4h 44m1 stop
Delta Logo
6:00 am - 2:14 pmMDW-CHO
7h 14m1 stop
$229Delta
Find Deal
Fri, May 30 - Mon, Jun 2
Delta Logo
5:30 pm - 10:41 pmCHO-ORD
6h 11m1 stop
Delta Logo
5:35 am - 10:53 amORD-CHO
4h 18m1 stop
$229Delta
Find Deal
Wed, Jun 4 - Tue, Jun 10
United Airlines Logo
7:59 pm - 11:15 pmCHO-ORD
4h 16m1 stop
United Airlines Logo
7:10 am - 10:10 amORD-CHO
2h 00mnonstop
$239United Airlines
Find Deal
Fri, May 16 - Sun, May 18
United Airlines Logo
7:00 am - 8:05 amCHO-ORD
2h 05mnonstop
United Airlines Logo
7:23 am - 10:25 amORD-CHO
2h 02mnonstop
$244United Airlines
Find Deal
Tue, May 27 - Sun, Jun 1
United Airlines Logo
8:15 pm - 11:15 pmCHO-ORD
4h 00m1 stop
United Airlines Logo
4:00 pm - 11:00 pmORD-CHO
6h 00m1 stop
$248United Airlines
Find Deal
Fri, Oct 17 - Sat, Oct 25
United Airlines Logo
7:59 pm - 11:15 pmCHO-ORD
4h 16m1 stop
United Airlines Logo
8:50 am - 1:38 pmORD-CHO
3h 48m1 stop
$249United Airlines
Find Deal
Fri, May 16 - Sun, May 18
American Airlines Logo
6:16 am - 10:41 amCHO-ORD
5h 25m1 stop
American Airlines Logo
5:00 am - 10:32 amORD-CHO
4h 32m1 stop
$274American Airlines
Find Deal
Sat, May 17 - Sun, May 18
American Airlines Logo
8:18 pm - 11:57 pmCHO-ORD
4h 39m1 stop
American Airlines Logo
7:05 am - 12:44 pmORD-CHO
4h 39m1 stop
$304American Airlines
Find Deal
Thu, Sep 25 - Sun, Sep 28
American Airlines Logo
2:13 pm - 9:13 pmCHO-ORD
8h 00m1 stop
American Airlines Logo
5:00 am - 10:32 amORD-CHO
4h 32m1 stop
$348American Airlines
Find Deal
Fri, May 23 - Mon, May 26
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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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Charlottesville to Chicago.

Our data shows that the cheapest route for a return flight from Charlottesville to Chicago cost $248 and was between Charlottesville (CHO) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $248.

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 Tuesday 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 $280 (return) on average. On the other hand, the most expensive months are November and September, where the average cost of round-trip tickets is $428 and $389 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 $611, 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 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonFebruary
High seasonAugust
Cheapest flight$116
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 6% increase in price.
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 $116 for a one-way ticket and $219 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?

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

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

    The Embraer 175 (Enhanced Winglets) 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 $380 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 $270 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 $276 or less one-way and $353 or less round-trip.

Prefer to fly direct from Charlottesville 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
See more direct flights

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 8696 reviews
6.6Food
7.7Boarding
8.1Crew
7.1Entertainment
7.3Comfort
Airline reviews

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.

10.0 ExcellentDr. Joseph, Apr 2025IAH - ORD
Read more United Airlines reviews

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

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was perfect except the pad at the top of the seat back. It pushes my head forward into a very uncomfortable position and it is not removable.

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

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

Information on your arrival and departure airports

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