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Cheap flights from Charlottesville to Chicago from $174

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 5/4. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
11:50 am - 3:27 pm
CHO
-
MDW
4h 37m
1 stop
Delta Logo
6:00 am - 11:16 am
MDW
-
CHO
4h 16m
1 stop
$237Delta
Wed, Sep 9 - Sat, Sep 12
Delta Logo
4:31 pm - 10:15 pm
CHO
-
ORD
6h 44m
1 stop
Delta Logo
5:15 am - 11:17 am
ORD
-
CHO
5h 02m
1 stop
$237Delta
Mon, Apr 13 - Mon, Apr 20
Delta Logo
5:54 pm - 11:59 pm
CHO
-
ORD
7h 05m
1 stop
Delta Logo
8:15 am - 1:50 pm
ORD
-
CHO
4h 35m
1 stop
$263Delta
Thu, Apr 23 - Tue, Apr 28
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
$269American Airlines
Fri, May 8 - Tue, Aug 25
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
Fri, Apr 17 - Fri, Apr 24
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
Wed, May 20 - Sat, May 23
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
$284American Airlines
Fri, May 8 - Mon, Aug 24
United Airlines Logo
8:30 am - 9:36 am
CHO
-
ORD
2h 06mnonstop
United Airlines Logo
6:55 am - 9:53 am
ORD
-
CHO
1h 58mnonstop
$287United Airlines
Fri, May 15 - Sun, May 17
United Airlines Logo
8:30 am - 9:36 am
CHO
-
ORD
2h 06mnonstop
United Airlines Logo
6:55 am - 9:53 am
ORD
-
CHO
1h 58mnonstop
$288United Airlines
Fri, May 1 - Sun, May 3
American Airlines Logo
8:10 pm - 11:54 pm
CHO
-
ORD
4h 44m
1 stop
American Airlines Logo
7:10 am - 12:30 pm
ORD
-
CHO
4h 20m
1 stop
$289American Airlines
Fri, May 8 - Tue, Aug 25

American Airlines flights from Charlottesville to Chicago

Our best American Airlines deals on Charlottesville to Chicago flight tickets
American Airlines
May 8
CHO8:10 pmCharlottesville Albemarle
4h 44m
1 stop
ORD11:54 pmChicago O'Hare Intl
Aug 25
ORD6:00 amChicago O'Hare Intl
7h 28m
1 stop
CHO2:28 pmCharlottesville Albemarle
$269
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
$284
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
$289

United Airlines flights from Charlottesville to Chicago

Our best United Airlines deals on Charlottesville to Chicago flight tickets
United Airlines
Apr 17
CHO8:25 pmCharlottesville Albemarle
4h 18m
1 stop
ORD11:43 pmChicago O'Hare Intl
Apr 19
ORD6:55 amChicago O'Hare Intl
2h 05m
CHO10:00 amCharlottesville Albemarle
$279
United Airlines
May 20
CHO2:55 pmCharlottesville Albemarle
2h 11m
ORD4:06 pmChicago O'Hare Intl
May 23
ORD5:45 pmChicago O'Hare Intl
2h 10m
CHO8:55 pmCharlottesville Albemarle
$280
United Airlines
May 15
CHO8:30 amCharlottesville Albemarle
2h 06m
ORD9:36 amChicago O'Hare Intl
May 17
ORD6:55 amChicago O'Hare Intl
1h 58m
CHO9:53 amCharlottesville Albemarle
$287

momondo Fare Finder

 
Customize your flight search to find flights from Charlottesville to Chicago 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 18, 2026.
Use the filters below to find and compare flights from Charlottesville to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 9/9

11:50 am-3:27 pm

1 stop4h 37m

Chicago Midway

Sat 9/12

6:00 am-11:16 am

1 stop4h 16m

$237

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Mon 4/13

4:31 pm-10:15 pm

1 stop6h 44m

Chicago O'Hare Intl

Mon 4/20

5:15 am-11:17 am

1 stop5h 02m

$237

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 4/23

5:54 pm-11:59 pm

1 stop7h 05m

Chicago O'Hare Intl

Tue 4/28

8:15 am-1:50 pm

1 stop4h 35m

$263

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

6:00 am-2:28 pm

1 stop7h 28m

$269

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 4/17

8:25 pm-11:43 pm

1 stop4h 18m

Chicago O'Hare Intl

Fri 4/24

6:55 am-10:00 am

Nonstop2h 05m

$279

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 5/20

2:55 pm-4:06 pm

Nonstop2h 11m

Chicago O'Hare Intl

Sat 5/23

5:45 pm-8:55 pm

Nonstop2h 10m

$280

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

$284
Quickest round-trip

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 5/15

8:30 am-9:36 am

Nonstop2h 06m

Chicago O'Hare Intl

Sun 5/17

6:55 am-9:53 am

Nonstop1h 58m

$287

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 5/1

8:30 am-9:36 am

Nonstop2h 06m

Chicago O'Hare Intl

Sun 5/3

6:55 am-9:53 am

Nonstop1h 58m

$288

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

7:10 am-12:30 pm

1 stop4h 20m

$289

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

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 typical price of a round-trip flight between Charlottesville and Chicago?

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Charlottesville, with most prices found around $249. If you’re not able to fly to Chicago in January, then November is your next best option. Flight prices from Charlottesville to Chicago during November average around $306.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $436. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Charlottesville to Chicago for around $690.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Charlottesville to Chicago during this time can be as low as $378. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $474.

What is the cheapest Charlottesville Albemarle to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Charlottesville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $400 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Charlottesville for as low as $209 on momondo.

What cabin class options are available on Charlottesville Albemarle to Chicago flights?

There are 4 cabin classes available to choose from on Charlottesville Albemarle to Chicago 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 flights?

You could potentially save up to 57% on your flight if you consider stops on a Charlottesville to Chicago flight.

When to book flights from Charlottesville to Chicago

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

Cheap Charlottesville to Chicago (CHO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Charlottesville to Chicago

Best Price Found

$243

Fastest flight time

2h 06m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Charlottesville in the past 72 hours is $243. The best round-trip flight deal from Charlottesville to Chicago found on momondo in the last 72 hours is $366.
The fastest flight from Charlottesville to Chicago takes 2h 06m
Direct flights go from Charlottesville to Chicago every day.
There are 3 airports in Chicago. From Charlottesville there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • How far is Charlottesville Albemarle to Chicago by plane?

    A flight from Charlottesville Albemarle to Chicago will travel around 551.8 mi. Typically, this will take 2h 06m by plane in normal conditions.

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

    Prices for flights from Charlottesville Albemarle Airport to Chicago were last updated today.

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

  • How old do you have to be to fly from Charlottesville Albemarle Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Charlottesville Albemarle Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago 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. 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?

  • What is the most popular airline from Charlottesville to Chicago?

Best airlines flying from Charlottesville to Chicago

Compare and see reviews for airlines that fly from Charlottesville to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $209Free CancellationRating
7.4
9,435 reviews
Search United Airlines flights
American AirlinesPriceFrom $228Free CancellationRating
7.1
11,468 reviews
Search American Airlines flights

  • United Airlines Flights From Charlottesville to Chicago

    United Airlines operates around 28 flights from Charlottesville to Chicago every week. The average price of these flights found in the last 72 hours has been $393, but momondo users have found United Airlines deals from Charlottesville to Chicago from as low as $209 round-trip. United Airlines has been scored 7.4/10 in 9,435 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Charlottesville to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. momondo enables you to select and highlight flights to Chicago from Charlottesville with this policy.

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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport