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Cheap flights from Charlottesville to Chicago from $207

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Charlottesville to Chicago departing on 5/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Charlottesville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
6:40 am - 7:51 am
CHO
-
ORD
2h 11mnonstop
United Airlines Logo
1:00 pm - 7:39 pm
ORD
-
CHO
5h 39m
1 stop
$253United Airlines
Fri, Apr 3 - Tue, Apr 7
United Airlines Logo
10:50 am - 4:51 pm
CHO
-
ORD
7h 01m
1 stop
United Airlines Logo
7:10 am - 10:09 am
ORD
-
CHO
1h 59mnonstop
$254United Airlines
Fri, Mar 6 - Sat, Mar 14
Delta Logo
4:31 pm - 9:23 am
CHO
-
ORD
17h 52m
1 stop
Delta Logo
7:14 am - 3:51 pm
ORD
-
CHO
7h 37m
1 stop
$256Delta
Fri, May 1 - Tue, May 5
Delta Logo
2:25 pm - 6:35 pm
CHO
-
ORD
5h 10m
1 stop
Delta Logo
6:00 am - 2:29 pm
ORD
-
CHO
7h 29m
1 stop
$258Delta
Fri, May 8 - Tue, Aug 25
American Airlines Logo
8:10 pm - 11:54 pm
CHO
-
ORD
4h 44m
1 stop
American Airlines Logo
6:55 am - 2:28 pm
ORD
-
CHO
6h 33m
1 stop
$259American Airlines
Fri, May 8 - Tue, Aug 25
United Airlines Logo
8:23 pm - 11:44 pm
CHO
-
ORD
4h 21m
1 stop
United Airlines Logo
8:45 am - 1:53 pm
ORD
-
CHO
4h 08m
1 stop
$262United Airlines
Thu, May 7 - Sun, May 10
Delta Logo
5:28 pm - 11:56 pm
CHO
-
ORD
7h 28m
1 stop
Delta Logo
5:30 am - 11:13 am
ORD
-
CHO
4h 43m
1 stop
$264Delta
Fri, Mar 6 - Fri, Mar 13
United Airlines Logo
8:20 am - 9:31 am
CHO
-
ORD
2h 11mnonstop
United Airlines Logo
6:55 am - 9:53 am
ORD
-
CHO
1h 58mnonstop
$269United Airlines
Wed, Apr 29 - Mon, May 4
American Airlines Logo
8:10 pm - 11:54 pm
CHO
-
ORD
4h 44m
1 stop
American Airlines Logo
6:00 am - 2:28 pm
ORD
-
CHO
7h 28m
1 stop
$274American Airlines
Fri, May 8 - Mon, Aug 24
Delta Logo
2:30 pm - 8:16 pm
CHO
-
ORD
6h 46m
1 stop
Delta Logo
7:44 pm - 2:47 pm
ORD
-
CHO
18h 03m
1 stop
$277Delta
Thu, Apr 30 - Fri, May 1

Delta flights from Charlottesville to Chicago O'Hare Intl Airport

Our best Delta deals on Charlottesville to Chicago O'Hare Intl Airport flight tickets
Delta
May 1
CHO4:31 pmCharlottesville Albemarle
17h 52m
1 stop
ORD9:23 amChicago O'Hare Intl
May 5
ORD7:14 amChicago O'Hare Intl
7h 37m
1 stop
CHO3:51 pmCharlottesville Albemarle
$256
Delta
May 8
CHO2:25 pmCharlottesville Albemarle
5h 10m
1 stop
ORD6:35 pmChicago O'Hare Intl
Aug 25
ORD6:00 amChicago O'Hare Intl
7h 29m
1 stop
CHO2:29 pmCharlottesville Albemarle
$258
Delta
Mar 6
CHO5:28 pmCharlottesville Albemarle
7h 28m
1 stop
ORD11:56 pmChicago O'Hare Intl
Mar 13
ORD5:30 amChicago O'Hare Intl
4h 43m
1 stop
CHO11:13 amCharlottesville Albemarle
$264

United Airlines flights from Charlottesville to Chicago O'Hare Intl Airport

Our best United Airlines deals on Charlottesville to Chicago O'Hare Intl Airport flight tickets
United Airlines
Apr 3
CHO6:40 amCharlottesville Albemarle
2h 11m
ORD7:51 amChicago O'Hare Intl
Apr 7
ORD1:00 pmChicago O'Hare Intl
5h 39m
1 stop
CHO7:39 pmCharlottesville Albemarle
$253
United Airlines
Mar 6
CHO10:50 amCharlottesville Albemarle
7h 01m
1 stop
ORD4:51 pmChicago O'Hare Intl
Mar 14
ORD7:10 amChicago O'Hare Intl
1h 59m
CHO10:09 amCharlottesville Albemarle
$254
United Airlines
May 7
CHO8:23 pmCharlottesville Albemarle
4h 21m
1 stop
ORD11:44 pmChicago O'Hare Intl
May 10
ORD8:45 amChicago O'Hare Intl
4h 08m
1 stop
CHO1:53 pmCharlottesville Albemarle
$262

momondo Fare Finder

 
Customize your flight search to find flights from Charlottesville to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 24, 2026.
Use the filters below to find and compare flights from Charlottesville to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 4/3

6:40 am-7:51 am

Nonstop2h 11m

Chicago O'Hare Intl

Tue 4/7

1:00 pm-7:39 pm

1 stop5h 39m

$253

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 3/6

10:50 am-4:51 pm

1 stop7h 01m

Chicago O'Hare Intl

Sat 3/14

7:10 am-10:09 am

Nonstop1h 59m

$254

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 5/1

4:31 pm-9:23 am

1 stop17h 52m

Chicago O'Hare Intl

Tue 5/5

7:14 am-3:51 pm

1 stop7h 37m

$256

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 5/8

2:25 pm-6:35 pm

1 stop5h 10m

Chicago O'Hare Intl

Tue 8/25

6:00 am-2:29 pm

1 stop7h 29m

$258

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 5/8

8:10 pm-11:54 pm

1 stop4h 44m

Chicago O'Hare Intl

Tue 8/25

6:55 am-2:28 pm

1 stop6h 33m

$259

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 5/7

8:23 pm-11:44 pm

1 stop4h 21m

Chicago O'Hare Intl

Sun 5/10

8:45 am-1:53 pm

1 stop4h 08m

$262

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 3/6

5:28 pm-11:56 pm

1 stop7h 28m

Chicago O'Hare Intl

Fri 3/13

5:30 am-11:13 am

1 stop4h 43m

$264

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 4/29

8:20 am-9:31 am

Nonstop2h 11m

Chicago O'Hare Intl

Mon 5/4

6:55 am-9:53 am

Nonstop1h 58m

$269

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 5/8

8:10 pm-11:54 pm

1 stop4h 44m

Chicago O'Hare Intl

Mon 8/24

6:00 am-2:28 pm

1 stop7h 28m

$274

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 4/30

2:30 pm-8:16 pm

1 stop6h 46m

Chicago O'Hare Intl

Fri 5/1

7:44 pm-2:47 pm

1 stop18h 03m

$277

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Charlottesville to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Charlottesville averaging around $349.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $426. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Charlottesville because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $687.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Charlottesville at noon is the least expensive time of day to depart. momondo users have found prices as low as $376 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $478. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Charlottesville Albemarle to Chicago O'Hare Intl flight route?

Fly from Charlottesville Albemarle to Chicago O'Hare Intl for the best Charlottesville Albemarle - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Charlottesville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $393 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Charlottesville for as low as $283 on momondo.

What cabin class options are available on Charlottesville Albemarle to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Charlottesville Albemarle to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Charlottesville to Chicago O'Hare Intl Airport flights?

You could potentially save up to 57% on your flight if you consider stops on a Charlottesville to Chicago O'Hare Intl Airport flight.

How have Charlottesville to Chicago O'Hare Intl Airport flight prices changed over time?

As of February 2026, prices for Charlottesville to Chicago O'Hare Intl Airport flights are approximately 158% more expensive when compared to flights at the same time last year.

When to book flights from Charlottesville to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Charlottesville to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Charlottesville to Chicago O'Hare Intl Airport (CHO to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Charlottesville to Chicago O'Hare Intl Airport

Best Price Found

$233

Fastest flight time

2h 10m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Charlottesville in the past 72 hours is $233. The best round-trip flight deal from Charlottesville to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $374.
The fastest flight from Charlottesville to Chicago O'Hare Intl Airport takes 2h 10m
Direct flights go from Charlottesville to Chicago O'Hare Intl Airport every day.
Search flight deals

  • How far is Charlottesville Albemarle to Chicago O'Hare Intl by plane?

    There are 567.7 mi between Charlottesville Albemarle and Chicago O'Hare Intl. Typically, this will take 2h 10m by plane in normal conditions.

  • When did momondo last update prices for flights from Charlottesville Albemarle Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Charlottesville Albemarle Airport to Chicago O'Hare Intl Airport are updated daily.

  • How many operators does momondo search for flights from Charlottesville Albemarle Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Charlottesville Albemarle Airport to Chicago O'Hare Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Charlottesville Albemarle Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Charlottesville to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Charlottesville to Chicago O'Hare Intl Airport?

Best airlines flying from Charlottesville to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Charlottesville to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $209Free CancellationRating
7.4
9,344 reviews
Search United Airlines flights
American AirlinesPriceFrom $228Free CancellationRating
7.2
11,344 reviews
Search American Airlines flights

  • United Airlines Flights From Charlottesville to Chicago O'Hare Intl Airport

    United Airlines is one of the most popular airlines flying from Charlottesville to Chicago O'Hare Intl Airport, operating 19 flights/week on average for this route. A good United Airlines flight deal for Charlottesville to Chicago O'Hare Intl Airport starts from $209 round-trip, up to an average price of $384. Our users have rated United Airlines at 7.4/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Kenosha
Orland Park
Oak Brook
Joliet
Racine
Janesville
Hammond
Aurora
Tinley Park
Elgin
South Holland

Why use momondo?

Why should I use momondo to find a flight deal from Charlottesville to Chicago?

It is quick and easy to find Charlottesville to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Charlottesville to Chicago with flexible booking policies on momondo?

All flight searches from Charlottesville to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Charlottesville to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Charlottesville to Chicago.

I’m not ready to book a flight from Charlottesville to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Charlottesville. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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