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$125+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — CHI
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Charlottesville Albemarle to Chicago are usually found in February or December, booked 77 days in advance, depart on a Wednesday or Thursday and return on a Tuesday

Cheap 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 August 14, 2025.

Round-trip from

$224
(Delta)

One-way from

$125
(Delta)

Popular in

June

Cheapest in

February

Average price

$389

Good round-trip deal

$493 or less

Good one-way deal

$295 or less
From Charlottesville Albemarle to Chicago (CHI)
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One-way flight from Charlottesville Albemarle to Chicago (CHI)
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Highest demand for flights based on searches. 14% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Charlottesville Albemarle to Chicago (CHI).
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Price to beat on a one-way flight from Charlottesville Albemarle to Chicago (CHI).
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Find 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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/14. 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.
Sat 11/156:00 amCHO - ORD
1 stop5h 03mDelta
Sat 12/67:00 amORD - CHO
1 stop6h 24mDelta
Deal found 8/14$224
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/122:42 pmCHO - ORD
1 stop5h 19mAmerican Airlines
Mon 9/155:00 amORD - CHO
1 stop4h 21mAmerican Airlines
Deal found 8/14$229
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 11/18:56 amCHO - ORD
1 stop6h 17mAmerican Airlines
Mon 11/35:00 amORD - CHO
1 stop5h 47mAmerican Airlines
Deal found 8/14$239
This American Airlines deal was found by Cheapflights users on 8/13. 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 9/196:51 pmCHO - ORD
1 stop5h 21mAmerican Airlines
Sun 9/215:00 amORD - CHO
1 stop4h 48mAmerican Airlines
Deal found 8/13$249
This United Airlines deal was found by Cheapflights users on 8/14. 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 8/275:41 pmCHO - ORD
Nonstop2h 06mUnited Airlines
Sun 8/316:15 pmORD - CHO
Nonstop2h 11mUnited Airlines
Deal found 8/14$259
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 10/44:53 pmCHO - ORD
1 stop7h 19mAmerican Airlines
Sat 10/118:15 amORD - CHO
1 stop5h 23mAmerican Airlines
Deal found 8/14$264
This Delta deal was found by Cheapflights users on 8/13. 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.
Tue 10/76:01 pmCHO - MDW
1 stop5h 13mDelta
Sat 10/114:23 pmMDW - CHO
1 stop5h 26mDelta
Deal found 8/13$269
This United Airlines deal was found by Cheapflights users on 8/12. 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 8/305:41 pmCHO - ORD
Nonstop2h 06mUnited Airlines
Sat 8/309:31 pmORD - CHO
2 stops11h 16mUnited Airlines
Deal found 8/12$274
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Mon 8/255:14 pmCHO - ORD
1 stop4h 26mAmerican Airlines
Sat 8/309:20 amORD - CHO
1 stop7h 23mAmerican Airlines
Deal found 8/14$279
This United Airlines deal was found by Cheapflights users on 8/14. 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 9/278:29 pmCHO - ORD
1 stop3h 46mUnited Airlines
Sat 10/48:45 amORD - CHO
Nonstop2h 12mUnited Airlines
Deal found 8/14$289
This Delta deal was found by Cheapflights users on 8/14. 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.
Thu 10/166:01 pmCHO - MDW
1 stop5h 13mDelta
Tue 10/216:00 amMDW - CHO
1 stop6h 50mDelta
Deal found 8/14$294
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/258:04 pmCHO - ORD
1 stop4h 35mAmerican Airlines
Sun 9/285:00 amORD - CHO
1 stop4h 48mAmerican Airlines
Deal found 8/14$294

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 August 14, 2025.
Use the filters below to find and compare flights from Charlottesville to Chicago that are best for you.

Fly from

Charlottesville

Fly to

Chicago

Route

Depart

Return

Price

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Sat 11/15

6:00 am-10:03 am

1 stop5h 03m

Chicago O'Hare Intl

Sat 12/6

7:00 am-2:24 pm

1 stop6h 24m

$224

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 9/25

8:04 pm-11:39 pm

1 stop4h 35m

Chicago O'Hare Intl

Mon 9/29

5:00 am-10:21 am

1 stop4h 21m

$229

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 8/28

7:00 am-8:05 am

Nonstop2h 05m

Chicago O'Hare Intl

Mon 9/1

7:19 am-10:24 am

Nonstop2h 05m

$229

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sat 1/17

4:05 pm-9:46 pm

1 stop6h 41m

Chicago Midway

Tue 1/20

6:00 am-2:26 pm

1 stop7h 26m

$229

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 9/11

5:00 am-9:25 am

1 stop5h 25m

Chicago O'Hare Intl

Thu 9/18

5:00 am-12:28 pm

1 stop6h 28m

$229

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Sat 11/1

8:56 am-2:13 pm

1 stop6h 17m

Chicago O'Hare Intl

Mon 11/3

5:00 am-11:47 am

1 stop5h 47m

$229

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 9/24

12:15 pm-7:17 pm

1 stop8h 02m

Chicago O'Hare Intl

Sat 9/27

6:00 pm-11:35 pm

1 stop4h 35m

$229

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 9/12

2:42 pm-7:01 pm

1 stop5h 19m

Chicago O'Hare Intl

Sat 9/20

8:37 am-2:52 pm

1 stop5h 15m

$229

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Mon 9/1

5:48 am-10:04 am

1 stop5h 16m

Chicago O'Hare Intl

Wed 9/3

5:45 am-11:11 am

1 stop4h 26m

$229

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 11/20

7:58 pm-11:40 pm

1 stop4h 42m

Chicago O'Hare Intl

Sun 11/23

5:00 am-10:25 am

1 stop4h 25m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 30 results
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2
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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

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

Use this chart to determine the optimal time to book a round-trip flight from Charlottesville to Chicago. Price data was last updated on August 8, 2025.

To ensure you get the cheapest price possible for a flight from Charlottesville to Chicago, you should look to book at least 77 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.

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

Currently, August is the cheapest month in which you can book a flight from Charlottesville to Chicago (average of $245). Flying from Charlottesville to Chicago in March is currently the most expensive (average of $321). 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 August 14, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 8% 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 August 14, 2025.

The most flights from CHO to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

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 August 14, 2025.
Peruse reviews from past customers who have flown with United Airlines and American 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
8,916 reviews

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

Crew

8.1

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
8,916 reviews
United Airlines
7.4
Good
8,916 reviews

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

Crew

8.1

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!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,916 reviews

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

Crew

8.1

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 3 daily outbound flights to Chicago from 2 different airlines.

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

    Cheapflights users have booked flights from Charlottesville to Chicago round-trip from $219. Another airline that can offer you cheap pricing is American Airlines. You may be able to fly from Charlottesville to Chicago for 44% 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 SkyWest Airlines (64%), United Airlines (64%) or Air New Zealand (58%) 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 $788 for a flight from Charlottesville to Chicago. The cheapest flight overall is $229 while the most popular route, (Charlottesville Albemarle - Chicago O'Hare Intl) is currently priced at $209.

  • 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, August is the cheapest month in which you can book a flight from Charlottesville to Chicago (average of $245). Flying from Charlottesville to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Charlottesville to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$219Average$405FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$228Average$308FlexibilityNo cancel feeOn-time71%

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