CHO - CHI

$184 Find Cheap Flights from Charlottesville to Chicago - Compare and Save

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 8/1. 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: $609-$334
United Airlines
Sat 9/12Mon 9/14
CHO - ORD • Non-stop
Cheapest non-stop
$269
Typical prices: $209-$449
United Airlines
Sat 11/14Mon 11/16
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 10m
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 $298 (round-trip)
Shortest trip • 4h 25m (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 33% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 26% 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

Sat, Sep 12 - Mon, Sep 14
United Airlines Logo
6:22 pm - 7:32 pm
CHO
-
ORD
2h 10mnonstop
United Airlines Logo
6:55 am - 10:01 am
ORD
-
CHO
2h 06mnonstop
$269United Airlines
Thu, Sep 17 - Mon, Sep 21
United Airlines Logo
6:45 am - 7:55 am
CHO
-
ORD
2h 10mnonstop
United Airlines Logo
4:00 pm - 11:44 pm
ORD
-
CHO
6h 44m
1 stop
$279United Airlines
Fri, Sep 11 - Wed, Sep 16
United Airlines Logo
6:45 am - 7:55 am
CHO
-
ORD
2h 10mnonstop
United Airlines Logo
6:55 am - 10:01 am
ORD
-
CHO
2h 06mnonstop
$284United Airlines
Wed, Sep 2 - Thu, Sep 10
Delta Logo
4:30 pm - 10:36 pm
CHO
-
MDW
7h 06m
1 stop
Delta Logo
6:05 am - 11:18 am
MDW
-
CHO
4h 13m
1 stop
$289Delta
Wed, Sep 2 - Wed, Sep 9
American Airlines Logo
6:02 am - 12:15 pm
CHO
-
ORD
7h 13m
1 stop
American Airlines Logo
5:20 am - 11:51 am
ORD
-
CHO
5h 31m
1 stop
$289American Airlines
Sat, Sep 5 - Fri, Sep 11
United Airlines Logo
2:57 pm - 6:37 pm
CHO
-
ORD
4h 40m
1 stop
United Airlines Logo
6:55 am - 10:01 am
ORD
-
CHO
2h 06mnonstop
$290United Airlines
Fri, Nov 6 - Mon, Nov 9
United Airlines Logo
1:55 pm - 2:53 pm
CHO
-
ORD
1h 58mnonstop
United Airlines Logo
4:25 pm - 10:57 pm
ORD
-
CHO
5h 32m
1 stop
$294United Airlines
Fri, Aug 14 - Mon, Aug 17
American Airlines Logo
7:21 pm - 11:52 pm
CHO
-
ORD
5h 31m
1 stop
American Airlines Logo
5:05 am - 12:11 pm
ORD
-
CHO
6h 06m
1 stop
$304American Airlines
Fri, Aug 7 - Mon, Aug 10
Delta Logo
5:38 pm - 10:36 pm
CHO
-
MDW
5h 58m
1 stop
Delta Logo
6:05 am - 11:32 am
MDW
-
CHO
4h 27m
1 stop
$309Delta
Tue, Jun 30 - Sat, Jul 4
Delta Logo
6:00 am - 10:09 am
CHO
-
MDW
5h 09m
1 stop
Delta Logo
6:00 am - 11:27 am
MDW
-
CHO
4h 27m
1 stop
$329Delta
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.

How much is a round-trip flight from Charlottesville to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Charlottesville to Chicago departing in September.

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 $290 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 Wednesday 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 $165 (return) on average. On the other hand, the most expensive months are May and March, where the average cost of round-trip tickets is $274 and $249 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 $423, 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 33% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonJune
Cheapest flight$184
Best time to beat the crowds but there is an average 33% increase in price.
Most popular time to fly and prices are also 10% 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 5 days, the lowest price for a flight from Charlottesville to Chicago was $184 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, JetBlue, 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.

  • 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 $318 or less one-way and $418 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 airline 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 9859 reviews
7.7Boarding
8.1Crew
7.1Entertainment
6.6Food
7.3Comfort
Airline reviews

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

2.0 MediocreLynn, Jun 2026
DCA - ORD
Read more United Airlines reviews

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

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

Information on your arrival and departure airports