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$209+ Cheap flights from Charlottesville (CHO) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — CHI
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 79 days in advance, depart on a Thursday or Wednesday and return on a Thursday

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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(United Airlines)

Popular in

June

Cheapest in

February

Average price

$484

Good round-trip deal

$310 or less

Good one-way deal

$228 or less
Provider with most accurate pricing for Charlottesville Albemarle-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Charlottesville Albemarle-Chicago (CHI) flights.
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From Charlottesville Albemarle to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 29, 2025.

This United Airlines deal was found by Cheapflights users on 9/29. 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 10/237:00 amCHO - ORD
Nonstop2h 05mUnited Airlines
Tue 10/287:25 amORD - CHO
Nonstop1h 55mUnited Airlines
Deal found 9/29$209
This United Airlines deal was found by Cheapflights users on 9/26. 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 10/177:00 amCHO - ORD
Nonstop2h 05mUnited Airlines
Mon 10/201:55 pmORD - CHO
Nonstop2h 12mUnited Airlines
Deal found 9/26$227
This Delta deal was found by Cheapflights users on 9/29. 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 10/235:35 amCHO - MDW
1 stop5h 05mDelta
Tue 10/286:00 amMDW - CHO
1 stop4h 11mDelta
Deal found 9/29$229
This Delta deal was found by Cheapflights users on 9/27. 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.
Sun 10/125:35 amCHO - MDW
1 stop5h 05mDelta
Tue 10/215:04 pmMDW - CHO
1 stop4h 45mDelta
Deal found 9/27$239
This American Airlines deal was found by Cheapflights users on 9/28. 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 10/167:57 pmCHO - ORD
1 stop4h 56mAmerican Airlines
Tue 10/216:00 amORD - CHO
1 stop6h 54mAmerican Airlines
Deal found 9/28$239
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Wed 10/157:18 pmCHO - ORD
1 stop4h 36mAmerican Airlines
Sat 10/185:20 amORD - CHO
1 stop4h 11mAmerican Airlines
Deal found 9/29$249
This American Airlines deal was found by Cheapflights users on 9/26. 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 10/177:57 pmCHO - ORD
1 stop4h 56mAmerican Airlines
Mon 10/205:22 amORD - CHO
1 stop4h 09mAmerican Airlines
Deal found 9/26$264
This Delta deal was found by Cheapflights users on 9/29. 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 10/165:35 amCHO - MDW
1 stop5h 05mDelta
Tue 10/215:04 pmMDW - CHO
1 stop4h 45mDelta
Deal found 9/29$269
This Delta deal was found by Cheapflights users on 9/27. 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 12/1711:15 amCHO - ORD
1 stop6h 33mDelta
Mon 1/55:50 amORD - CHO
1 stop4h 23mDelta
Deal found 9/27$269
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/245:48 pmCHO - ORD
Nonstop2h 07mUnited Airlines
Tue 10/287:25 amORD - CHO
Nonstop1h 55mUnited Airlines
Deal found 9/28$270
This United Airlines deal was found by Cheapflights users on 9/27. 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 11/78:10 pmCHO - ORD
1 stop4h 33mUnited Airlines
Sat 11/157:25 amORD - CHO
Nonstop1h 55mUnited Airlines
Deal found 9/27$274
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/237:00 amCHO - ORD
Nonstop2h 05mUnited Airlines
Sun 10/267:25 amORD - CHO
Nonstop1h 55mUnited Airlines
Deal found 9/28$279

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 September 29, 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

Wed 12/3

6:10 am-11:51 am

1 stop6h 41m

Chicago O'Hare Intl

Mon 12/8

7:20 am-10:15 am

Nonstop1h 55m

$219

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 12/16

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Mon 1/5

6:00 am-11:13 am

1 stop4h 13m

$229

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 11/19

6:06 pm-11:40 pm

1 stop6h 34m

Chicago Midway

Wed 12/3

6:00 am-2:22 pm

1 stop7h 22m

$229

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 10/24

8:29 pm-11:15 pm

1 stop3h 46m

Chicago O'Hare Intl

Tue 10/28

1:00 pm-7:31 pm

1 stop5h 31m

$229

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 12/16

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Tue 1/6

6:00 am-11:13 am

1 stop4h 13m

$229

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Fri 10/24

6:01 pm-10:14 pm

1 stop5h 13m

Chicago Midway

Tue 10/28

6:00 am-11:11 am

1 stop4h 11m

$229

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 10/24

6:01 pm-11:58 pm

1 stop6h 57m

Chicago O'Hare Intl

Mon 10/27

4:05 pm-10:49 pm

1 stop5h 44m

$229

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 12/18

6:00 am-10:14 am

1 stop5h 14m

Chicago O'Hare Intl

Tue 1/6

5:50 am-11:13 am

1 stop4h 23m

$229

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Wed 10/15

6:01 pm-10:14 pm

1 stop5h 13m

Chicago Midway

Tue 10/21

5:04 pm-10:49 pm

1 stop4h 45m

$239

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sun 10/12

5:35 am-9:40 am

1 stop5h 05m

Chicago Midway

Tue 10/21

5:04 pm-10:49 pm

1 stop4h 45m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/28

Showing 1-10 of 43 results
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Compare providers for flights from Charlottesville to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Charlottesville to Chicago in September.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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

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 September 26, 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 September 29, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 6% 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 September 29, 2025.

The most flights from CHO to CHI are scheduled on a Sunday (7 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?

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 September 29, 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
8,924 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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 $229, United Airlines can have you in Chicago from Charlottesville in 4h 54m. There are 552 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 $219. Another airline that can offer you cheap pricing is American Airlines. You may be able to fly from Charlottesville to Chicago for 45% 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 (74%), United Airlines (74%) or Air New Zealand (63%) 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 $562 for a flight from Charlottesville to Chicago. The cheapest flight overall is $138 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

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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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$219Average$386FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$228Average$308FlexibilityNo cancel feeOn-time71%

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