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$184+ Cheap flights from Charlottesville (CHO) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — CHI
Aug 19 — Aug 261
Wed 8/19
Wed 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Charlottesville Albemarle to Chicago are usually found in January or November, booked 79 days in advance, depart on a Saturday or Thursday and return on a Saturday

Cheap flight deals from Charlottesville to Chicago

Cheapest flights from Charlottesville to Chicago
Explore the most affordable flight options available from Charlottesville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 20, 2026.

This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:42 pm
CHO
-
ORD
Nonstop2h 10m
American Airlines
Wed 12/22:01 pm
ORD
-
CHO
Nonstop2h 10m
American Airlines
Deal found 7/19$269
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:50 am
CHO
-
ORD
Nonstop2h 07m
United Airlines
Tue 9/85:59 pm
ORD
-
CHO
Nonstop2h 11m
United Airlines
Deal found 7/20$284
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:30 pm
CHO
-
MDW
1 stop7h 06m
Delta
Thu 9/104:30 pm
MDW
-
CHO
1 stop4h 26m
Delta
Deal found 7/16$289
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:17 pm
CHO
-
ORD
1 stop5h 34m
Delta
Thu 9/101:50 pm
ORD
-
CHO
1 stop7h 06m
Delta
Deal found 7/16$289
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:25 am
CHO
-
ORD
1 stop4h 11m
United Airlines
Sun 8/96:55 am
ORD
-
CHO
Nonstop2h 01m
United Airlines
Deal found 7/16$290
This United Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:59 pm
CHO
-
ORD
1 stop4h 33m
United Airlines
Mon 10/198:45 am
ORD
-
CHO
Nonstop2h 12m
United Airlines
Deal found 7/18$294
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:16 pm
CHO
-
ORD
1 stop4h 44m
American Airlines
Sat 9/126:45 am
ORD
-
CHO
1 stop7h 23m
American Airlines
Deal found 7/17$295
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:46 am
CHO
-
ORD
Nonstop2h 05m
United Airlines
Mon 11/27:02 am
ORD
-
CHO
Nonstop1h 56m
United Airlines
Deal found 7/19$296
This United Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/12:56 pm
CHO
-
ORD
1 stop6h 36m
United Airlines
Mon 8/106:55 am
ORD
-
CHO
Nonstop2h 01m
United Airlines
Deal found 7/17$299
This American Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:21 pm
CHO
-
ORD
1 stop5h 31m
American Airlines
Sun 8/165:05 am
ORD
-
CHO
1 stop4h 28m
American Airlines
Deal found 7/17$304
This United Airlines deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:25 am
CHO
-
ORD
1 stop4h 11m
United Airlines
Sun 8/96:55 am
ORD
-
CHO
Nonstop2h 01m
United Airlines
Deal found 7/16$306
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:57 pm
CHO
-
ORD
Nonstop2h 07m
United Airlines
Fri 8/286:59 am
ORD
-
CHO
Nonstop2h 06m
United Airlines
Deal found 7/20$307

Find flight deals from Charlottesville to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Charlottesville (CHO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(American Airlines)

One-way from

$184
(American Airlines)

Popular in

June

Cheapest in

January

Average price

$473

Good round-trip deal

$427 or less

Good one-way deal

$339 or less
Provider with most accurate pricing for Charlottesville Albemarle-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Charlottesville Albemarle-Chicago (CHI) flights.
Search Deals
From Charlottesville Albemarle to Chicago (CHI)
Search Deals
One-way flight from Charlottesville Albemarle to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($74 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Charlottesville Albemarle to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Charlottesville Albemarle to Chicago (CHI).
Search Deals

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated July 20, 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
Quickest round-trip

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 11/4

2:20 pm-3:18 pm

Nonstop1h 58m

Chicago O'Hare Intl

Mon 11/9

7:02 am-9:58 am

Nonstop1h 56m

$269

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 9/10

6:25 am-9:38 am

1 stop4h 13m

Chicago O'Hare Intl

Sun 9/13

6:55 am-10:01 am

Nonstop2h 06m

$279

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sat 9/5

4:26 pm-10:36 pm

1 stop7h 10m

Chicago Midway

Tue 9/8

6:05 am-11:18 am

1 stop4h 13m

$289

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 11/5

5:31 pm-10:25 pm

1 stop5h 54m

Chicago Midway

Tue 11/10

6:00 am-2:27 pm

1 stop7h 27m

$289

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sat 10/3

4:20 pm-10:44 pm

1 stop7h 24m

Chicago Midway

Wed 10/14

6:00 am-11:14 am

1 stop4h 14m

$289

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 8/20

5:38 pm-10:36 pm

1 stop5h 58m

Chicago Midway

Mon 8/24

6:05 am-1:52 pm

1 stop6h 47m

$344

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Fri 9/11

4:20 pm-10:44 pm

1 stop7h 24m

Chicago Midway

Sun 9/13

6:05 am-11:18 am

1 stop4h 13m

$344

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Sat 8/1

5:52 pm-7:00 pm

Nonstop2h 08m

Chicago O'Hare Intl

Sat 8/8

6:55 am-9:56 am

Nonstop2h 01m

$345

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 8/26

5:57 pm-7:04 pm

Nonstop2h 07m

Chicago O'Hare Intl

Sun 8/30

6:59 am-10:05 am

Nonstop2h 06m

$349

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 9/10

6:25 am-9:38 am

1 stop4h 13m

Chicago O'Hare Intl

Sat 9/12

6:55 am-10:01 am

Nonstop2h 06m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/15

Showing 1-10 of 36 resultsSorted by cheapest first
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  • Most accurate provider: When it comes to deals on Charlottesville-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Charlottesville-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Charlottesville-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Charlottesville-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Charlottesville-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Charlottesville to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Charlottesville with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Charlottesville to Chicago?

Currently, November is the cheapest month in which you can book a flight from Charlottesville to Chicago (average of $293). Flying from Charlottesville to Chicago in September is currently the most expensive (average of $476). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHO to CHI?

Find hourly flight availability from Charlottesville to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 20, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 17% on flights from Charlottesville to Chicago by exploring options for tickets at noon.

Weekly flight availability from Charlottesville to Chicago

Explore weekly flight availability from Charlottesville to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 20, 2026.

The most flights from CHO to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).

How much does it cost to fly round-trip from Charlottesville to Chicago?

How far ahead should I book a flight from Charlottesville to Chicago?

To ensure you get the cheapest price possible for a flight from Charlottesville to Chicago, you should look to book at least 28 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 20, 2026.
Peruse reviews from past customers who have flown with United Airlines from Charlottesville to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
10,013 reviews

Food

6.6

Entertainment

7.1

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
10,013 reviews
United Airlines
7.4
Good
10,013 reviews

Food

6.6

Entertainment

7.1

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Charlottesville to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Charlottesville to Chicago?

    Located just 7.6 mi from the city center, Charlottesville Albemarle is the airport most travelers will use when flying to Chicago from Charlottesville. Booking flights from Albemarle (CHO) to Chicago should be relatively easy as there are 5 daily outbound flights to Chicago from 2 different airlines.

  • How long is the flight from Charlottesville to Chicago?

    For as low as $269, United Airlines can have you in Chicago from Charlottesville in 1h 58m. There are 565 mi between Charlottesville and Chicago. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Charlottesville to Chicago round-trip?

    Cheapflights users have booked flights from Charlottesville to Chicago round-trip from $209. Another airline that can offer you cheap pricing is American Airlines. You may be able to fly from Charlottesville to Chicago for 46% less than the average price by searching for these airlines.

  • What are the most reliable airlines from Charlottesville to Chicago?

    No one likes to see their flight delayed. When booking a flight from Charlottesville to Chicago consider choosing Air New Zealand (78%), SkyWest Airlines (69%) or United Airlines (69%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Charlottesville to Chicago?

    On average you can expect to pay $460 for a flight from Charlottesville to Chicago. The cheapest flight overall is $234 while the most popular route, (Charlottesville Albemarle - Chicago O'Hare Intl) is currently priced at $269.

  • Can I find deals for flights from Charlottesville to Chicago that include hotel bookings?

    Yes. In addition to deals on Charlottesville to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Charlottesville to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Charlottesville to Chicago.

  • Can I find deals for business class flights from Charlottesville to Chicago?

    Yes. Cheapflights offers flight deals from Charlottesville to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Charlottesville to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Charlottesville to Chicago (average of $293). Flying from Charlottesville to Chicago in September is currently the most expensive (average of $476). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Top 2 airlines flying from Charlottesville to Chicago

Discover the top 2 airlines that operate flights from Charlottesville to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$209Average$405FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$288Average$423FlexibilityNo cancel feeOn-time71%

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