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Cheap flights from Charlottesville to Chicago from $209

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Charlottesville to Chicago departing on 10/4. 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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Find the cheapest flights from Charlottesville to Chicago

Cheap round-trip flights

United Airlines Logo
12:38 pm - 1:47 pmCHO-ORD
2h 09mnonstop
United Airlines Logo
6:30 pm - 9:50 pmORD-CHO
2h 20mnonstop
$209United Airlines
Find Deal
Sat, Oct 4 - Mon, Oct 6
United Airlines Logo
8:29 pm - 11:15 pmCHO-ORD
3h 46m1 stop
United Airlines Logo
7:49 am - 10:48 amORD-CHO
1h 59mnonstop
$219United Airlines
Find Deal
Mon, Sep 29 - Mon, Oct 6
United Airlines Logo
8:29 pm - 11:15 pmCHO-ORD
3h 46m1 stop
United Airlines Logo
12:55 pm - 6:52 pmORD-CHO
4h 57m1 stop
$229United Airlines
Find Deal
Mon, Sep 29 - Mon, Oct 6
United Airlines Logo
8:29 pm - 11:15 pmCHO-ORD
3h 46m1 stop
United Airlines Logo
7:25 am - 10:20 amORD-CHO
1h 55mnonstop
$236United Airlines
Find Deal
Thu, Oct 23 - Mon, Oct 27
United Airlines Logo
8:10 pm - 11:44 pmCHO-ORD
4h 34m1 stop
United Airlines Logo
7:20 am - 10:15 amORD-CHO
1h 55mnonstop
$237United Airlines
Find Deal
Mon, Nov 24 - Fri, Dec 12
United Airlines Logo
5:41 pm - 6:51 pmCHO-ORD
2h 10mnonstop
United Airlines Logo
5:55 pm - 11:44 pmORD-CHO
4h 49m1 stop
$239United Airlines
Find Deal
Wed, Sep 17 - Sat, Sep 20
American Airlines Logo
9:58 am - 2:47 pmCHO-ORD
5h 49m1 stop
American Airlines Logo
12:33 pm - 5:46 pmORD-CHO
4h 13m1 stop
$249American Airlines
Find Deal
Sat, Sep 27 - Sat, Oct 4
American Airlines Logo
10:52 am - 2:17 pmCHO-ORD
4h 25m1 stop
American Airlines Logo
10:30 am - 5:39 pmORD-CHO
6h 09m1 stop
$259American Airlines
Find Deal
Thu, Dec 11 - Sat, Dec 13
American Airlines Logo
2:42 pm - 7:01 pmCHO-ORD
5h 19m1 stop
American Airlines Logo
5:00 am - 10:48 amORD-CHO
4h 48m1 stop
$264American Airlines
Find Deal
Thu, Sep 25 - Sun, Sep 28
Delta Logo
6:29 am - 4:28 pmCHO-ORD
10h 59m2 stops
Delta Logo
6:45 am - 2:24 pmORD-CHO
6h 39m1 stop
$277Delta
Find Deal
Wed, Nov 19 - Mon, Nov 24

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
Nov 19
CHO6:29 amCharlottesville Albemarle
10h 59m
2 stops
ORD4:28 pmChicago O'Hare Intl
Nov 24
ORD6:45 amChicago O'Hare Intl
6h 39m
1 stop
CHO2:24 pmCharlottesville Albemarle
$277
Find similar
Delta
Sep 10
CHO7:01 amCharlottesville Albemarle
6h 44m
2 stops
ORD12:45 pmChicago O'Hare Intl
Sep 16
ORD5:30 amChicago O'Hare Intl
4h 54m
1 stop
CHO11:24 amCharlottesville Albemarle
$729
Find similar
Delta
Sep 10
CHO4:08 pmCharlottesville Albemarle
7h 29m
1 stop
ORD10:37 pmChicago O'Hare Intl
Sep 12
ORD2:45 pmChicago O'Hare Intl
7h 16m
1 stop
CHO11:01 pmCharlottesville Albemarle
$807
Find similar

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
Oct 4
CHO12:38 pmCharlottesville Albemarle
2h 09m
ORD1:47 pmChicago O'Hare Intl
Oct 6
ORD6:30 pmChicago O'Hare Intl
2h 20m
CHO9:50 pmCharlottesville Albemarle
$209
Find similar
United Airlines
Sep 29
CHO8:29 pmCharlottesville Albemarle
3h 46m
1 stop
ORD11:15 pmChicago O'Hare Intl
Oct 6
ORD7:49 amChicago O'Hare Intl
1h 59m
CHO10:48 amCharlottesville Albemarle
$219
Find similar
United Airlines
Sep 29
CHO8:29 pmCharlottesville Albemarle
3h 46m
1 stop
ORD11:15 pmChicago O'Hare Intl
Oct 6
ORD12:55 pmChicago O'Hare Intl
4h 57m
1 stop
CHO6:52 pmCharlottesville Albemarle
$229
Find similar

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 September 3, 2025.
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

Sat 10/4

12:38 pm-1:47 pm

Nonstop2h 09m

Chicago O'Hare Intl

Mon 10/6

6:30 pm-9:50 pm

Nonstop2h 20m

$209

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Mon 9/29

8:29 pm-11:15 pm

1 stop3h 46m

Chicago O'Hare Intl

Mon 10/6

7:49 am-10:48 am

Nonstop1h 59m

$219

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Mon 9/29

8:29 pm-11:15 pm

1 stop3h 46m

Chicago O'Hare Intl

Mon 10/6

12:55 pm-6:52 pm

1 stop4h 57m

$229

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 10/23

8:29 pm-11:15 pm

1 stop3h 46m

Chicago O'Hare Intl

Mon 10/27

7:25 am-10:20 am

Nonstop1h 55m

$236

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Mon 11/24

8:10 pm-11:44 pm

1 stop4h 34m

Chicago O'Hare Intl

Fri 12/12

7:20 am-10:15 am

Nonstop1h 55m

$237

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 9/17

5:41 pm-6:51 pm

Nonstop2h 10m

Chicago O'Hare Intl

Sat 9/20

5:55 pm-11:44 pm

1 stop4h 49m

$239

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Sat 9/27

9:58 am-2:47 pm

1 stop5h 49m

Chicago O'Hare Intl

Sat 10/4

12:33 pm-5:46 pm

1 stop4h 13m

$249

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 12/11

10:52 am-2:17 pm

1 stop4h 25m

Chicago O'Hare Intl

Sat 12/13

10:30 am-5:39 pm

1 stop6h 09m

$259

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 9/25

2:42 pm-7:01 pm

1 stop5h 19m

Chicago O'Hare Intl

Sun 9/28

5:00 am-10:48 am

1 stop4h 48m

$264

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 11/19

6:29 am-4:28 pm

2 stops10h 59m

Chicago O'Hare Intl

Mon 11/24

6:45 am-2:24 pm

1 stop6h 39m

$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 January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Charlottesville averaging around $331.

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 $444. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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 $639.

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 in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $476 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $515. 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 $395 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 $322 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 9% on your flight if you consider stops on a Charlottesville to Chicago O'Hare Intl Airport flight.

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

$277

Fastest flight time

2h 04m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Charlottesville in the past 72 hours is $277. The best round-trip flight deal from Charlottesville to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $411.
The fastest flight from Charlottesville to Chicago O'Hare Intl Airport takes 2h 04m
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 1h 58m 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 $219Free CancellationRating
7.4
8,937 reviews
Search United Airlines flights
American AirlinesPriceFrom $228Free CancellationRating
7.2
10,000 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 20 flights/week on average for this route. A good United Airlines flight deal for Charlottesville to Chicago O'Hare Intl Airport starts from $219 round-trip, up to an average price of $403. 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
South Haven
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
Aurora
Janesville
Benton Harbor

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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