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 4/25. 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
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Everything you should know

Cheapest round-trip
$269
Typical prices: $291-$463
United Airlines
Fri 5/8Sun 5/10
CHO - ORD • 1 stop
Cheapest non-stop
$278
Typical prices: $289-$547
United Airlines
Tue 4/7Sat 4/11
CHO - ORD • Non-stop
Top airlines
Cheapest • from $269 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with United Airlines. Average duration is 2h 11m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $295 (round-trip)
Shortest trip • 4h 46m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 25% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 36% price drop
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

Fri, May 8 - Sun, May 10
United Airlines Logo
8:23 pm - 11:44 pm
CHO
-
ORD
4h 21m
1 stop
United Airlines Logo
4:25 pm - 11:28 pm
ORD
-
CHO
6h 03m
1 stop
$269United Airlines
Thu, May 14 - Sat, May 16
United Airlines Logo
2:55 pm - 4:06 pm
CHO
-
ORD
2h 11mnonstop
United Airlines Logo
12:55 pm - 7:25 pm
ORD
-
CHO
5h 30m
1 stop
$271United Airlines
Tue, Apr 7 - Sat, Apr 11
United Airlines Logo
5:54 pm - 7:05 pm
CHO
-
ORD
2h 11mnonstop
United Airlines Logo
9:50 pm - 12:53 am
ORD
-
CHO
2h 03mnonstop
$278United Airlines
Fri, Apr 17 - Fri, Apr 24
United Airlines Logo
8:25 pm - 11:43 pm
CHO
-
ORD
4h 18m
1 stop
United Airlines Logo
6:55 am - 10:00 am
ORD
-
CHO
2h 05mnonstop
$279United Airlines
Wed, May 20 - Sat, May 23
United Airlines Logo
2:55 pm - 4:06 pm
CHO
-
ORD
2h 11mnonstop
United Airlines Logo
5:45 pm - 8:55 pm
ORD
-
CHO
2h 10mnonstop
$280United Airlines
Fri, May 8 - Mon, Aug 24
American Airlines Logo
5:08 am - 10:44 am
CHO
-
ORD
6h 36m
1 stop
American Airlines Logo
6:00 am - 2:28 pm
ORD
-
CHO
7h 28m
1 stop
$284American Airlines
Thu, Aug 27 - Sat, Aug 29
Delta Logo
3:05 pm - 9:46 pm
CHO
-
MDW
7h 41m
1 stop
Delta Logo
6:00 am - 11:16 am
MDW
-
CHO
4h 16m
1 stop
$289Delta
Tue, Apr 7 - Sat, Apr 11
American Airlines Logo
7:13 pm - 11:54 pm
CHO
-
ORD
5h 41m
1 stop
American Airlines Logo
7:15 am - 3:12 pm
ORD
-
CHO
6h 57m
1 stop
$293American Airlines
Fri, May 8 - Sun, May 10
Delta Logo
2:25 pm - 9:09 pm
CHO
-
MDW
7h 44m
1 stop
Delta Logo
6:23 am - 1:46 pm
MDW
-
CHO
6h 23m
1 stop
$324Delta
Thu, Sep 3 - Sat, Sep 5
Delta Logo
3:05 pm - 9:46 pm
CHO
-
MDW
7h 41m
1 stop
Delta Logo
6:00 am - 11:16 am
MDW
-
CHO
4h 16m
1 stop
$348Delta
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 $279 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 Monday 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 $249 (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 $494 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $366 on average.

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 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$134
Best time to beat the crowds with an average 2% 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 $134 for a one-way ticket and $269 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: American Airlines, United Airlines, Alaska Airlines, Delta, Hawaiian Airlines, and Lufthansa.

  • 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 $390 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 $343 and an overall rating of 7.1.

  • 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 $243 or less one-way and $366 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 9428 reviews
8.1Crew
7.7Boarding
7.1Entertainment
7.3Comfort
6.6Food
Airline reviews

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

10.0 ExcellentDr. Joseph, Feb 2026
DCA - ORD
Read more United Airlines reviews

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

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

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

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

Information on your arrival and departure airports