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Cheap flights from Charlottesville to Chicago from $144

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 4/15. 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
10:50 am - 4:51 pm
CHO
-
ORD
7h 01m
1 stop
United Airlines Logo
2:30 pm - 7:42 pm
ORD
-
CHO
4h 12m
1 stop
$258United Airlines
Fri, Mar 20 - Mon, Mar 23
United Airlines Logo
6:40 am - 7:51 am
CHO
-
ORD
2h 11mnonstop
United Airlines Logo
9:50 pm - 12:53 am
ORD
-
CHO
2h 03mnonstop
$259United Airlines
Mon, Mar 30 - Mon, Apr 6
United Airlines Logo
8:30 am - 9:42 am
CHO
-
ORD
2h 12mnonstop
United Airlines Logo
7:10 am - 10:09 am
ORD
-
CHO
1h 59mnonstop
$262United Airlines
Wed, Mar 18 - Sun, Mar 22
American Airlines Logo
8:10 pm - 11:54 pm
CHO
-
ORD
4h 44m
1 stop
American Airlines Logo
6:25 pm - 12:12 am
ORD
-
CHO
4h 47m
1 stop
$264American Airlines
Fri, May 8 - Sat, Aug 22
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
$268American Airlines
Fri, May 8 - Mon, Aug 24
United Airlines Logo
6:20 am - 9:49 am
CHO
-
ORD
4h 29m
1 stop
United Airlines Logo
7:10 am - 10:09 am
ORD
-
CHO
1h 59mnonstop
$272United Airlines
Wed, Mar 18 - Sun, Mar 22
American Airlines Logo
8:10 pm - 11:54 pm
CHO
-
ORD
4h 44m
1 stop
American Airlines Logo
4:56 pm - 12:12 am
ORD
-
CHO
6h 16m
1 stop
$274American Airlines
Fri, May 8 - Sat, Aug 22
Delta Logo
2:27 pm - 6:53 pm
CHO
-
ORD
5h 26m
1 stop
Delta Logo
2:59 pm - 10:48 pm
ORD
-
CHO
6h 49m
1 stop
$278Delta
Tue, Mar 31 - Sat, Apr 4
United Airlines Logo
2:49 pm - 4:00 pm
CHO
-
ORD
2h 11mnonstop
United Airlines Logo
9:50 pm - 12:53 am
ORD
-
CHO
2h 03mnonstop
$279United Airlines
Thu, Apr 16 - Sat, Apr 18
United Airlines Logo
10:45 am - 11:57 am
CHO
-
ORD
2h 12mnonstop
United Airlines Logo
9:15 pm - 12:09 am
ORD
-
CHO
1h 54mnonstop
$280United Airlines
Fri, Mar 13 - Sat, Mar 21

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
Mar 16
CHO6:06 pmCharlottesville Albemarle
6h 48m
1 stop
ORD11:54 pmChicago O'Hare Intl
Mar 24
ORD5:30 amChicago O'Hare Intl
4h 43m
1 stop
CHO11:13 amCharlottesville Albemarle
$288
Delta
Mar 6
CHO2:34 pmCharlottesville Albemarle
7h 05m
1 stop
ORD8:39 pmChicago O'Hare Intl
Mar 17
ORD5:30 amChicago O'Hare Intl
4h 43m
1 stop
CHO11:13 amCharlottesville Albemarle
$304
Delta
Mar 19
CHO7:00 amCharlottesville Albemarle
7h 33m
1 stop
ORD1:33 pmChicago O'Hare Intl
Mar 23
ORD2:40 pmChicago O'Hare Intl
6h 57m
1 stop
CHO10:37 pmCharlottesville Albemarle
$314

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

Our best American Airlines deals on Charlottesville to Chicago O'Hare Intl Airport flight tickets
American Airlines
May 8
CHO8:10 pmCharlottesville Albemarle
4h 44m
1 stop
ORD11:54 pmChicago O'Hare Intl
Aug 24
ORD6:00 amChicago O'Hare Intl
7h 28m
1 stop
CHO2:28 pmCharlottesville Albemarle
$268
American Airlines
May 8
CHO5:08 amCharlottesville Albemarle
6h 36m
1 stop
ORD10:44 amChicago O'Hare Intl
Aug 25
ORD8:20 amChicago O'Hare Intl
5h 08m
1 stop
CHO2:28 pmCharlottesville Albemarle
$274
American Airlines
Mar 24
CHO8:02 amCharlottesville Albemarle
7h 14m
1 stop
ORD2:16 pmChicago O'Hare Intl
Mar 25
ORD11:55 amChicago O'Hare Intl
5h 06m
1 stop
CHO6:01 pmCharlottesville Albemarle
$307

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 March 3, 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 3/20

10:50 am-4:51 pm

1 stop7h 01m

Chicago O'Hare Intl

Mon 3/23

2:30 pm-7:42 pm

1 stop4h 12m

$258

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Mon 3/30

6:40 am-7:51 am

Nonstop2h 11m

Chicago O'Hare Intl

Mon 4/6

9:50 pm-12:53 am

Nonstop2h 03m

$259

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 3/18

8:30 am-9:42 am

Nonstop2h 12m

Chicago O'Hare Intl

Sun 3/22

7:10 am-10:09 am

Nonstop1h 59m

$262

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 5/8

8:10 pm-11:54 pm

1 stop4h 44m

Chicago O'Hare Intl

Sat 8/22

6:25 pm-12:12 am

1 stop4h 47m

$264

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

$268

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 3/18

6:20 am-9:49 am

1 stop4h 29m

Chicago O'Hare Intl

Sun 3/22

7:10 am-10:09 am

Nonstop1h 59m

$272

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 5/8

8:10 pm-11:54 pm

1 stop4h 44m

Chicago O'Hare Intl

Sat 8/22

4:56 pm-12:12 am

1 stop6h 16m

$274

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Tue 3/31

2:27 pm-6:53 pm

1 stop5h 26m

Chicago O'Hare Intl

Sat 4/4

2:59 pm-10:48 pm

1 stop6h 49m

$278

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 4/16

2:49 pm-4:00 pm

Nonstop2h 11m

Chicago O'Hare Intl

Sat 4/18

9:50 pm-12:53 am

Nonstop2h 03m

$279

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 3/13

10:45 am-11:57 am

Nonstop2h 12m

Chicago O'Hare Intl

Sat 3/21

9:15 pm-12:09 am

Nonstop1h 54m

$280

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 March 2026, prices for Charlottesville to Chicago O'Hare Intl Airport flights are approximately 4% cheaper 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

$238

Fastest flight time

2h 09m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Charlottesville in the past 72 hours is $238. The best round-trip flight deal from Charlottesville to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $371.
The fastest flight from Charlottesville to Chicago O'Hare Intl Airport takes 2h 09m
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 09m 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
9,377 reviews
Search United Airlines flights
American AirlinesPriceFrom $228Free CancellationRating
7.1
11,375 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 12 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 $387. 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
Naperville
Rosemont
New Buffalo
Orland Park
Kenosha
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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