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$83+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — CHI
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 Wednesday or Thursday 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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$175
(Delta)

One-way from

$83
(Delta)

Popular in

September

Cheapest in

January

Average price

$279

Good round-trip deal

$339 or less

Good one-way deal

$278 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)
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One-way flight from Charlottesville Albemarle to Chicago (CHI)
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Highest demand for flights based on searches. 11% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 8, 2026.

This Delta deal was found by Cheapflights users on 1/8. 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.
Fri 2/66:00 amCHO - MDW
1 stop4h 53mDelta
Tue 2/106:00 amMDW - CHO
1 stop7h 12mDelta
Deal found 1/8$165
This Delta deal was found by Cheapflights users on 1/8. 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.
Fri 2/63:02 pmCHO - ORD
1 stop4h 47mDelta
Tue 2/102:50 pmORD - CHO
1 stop7h 01mDelta
Deal found 1/8$165
This Delta deal was found by Cheapflights users on 1/7. 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 1/2911:58 amCHO - MDW
1 stop6h 31mDelta
Sun 2/16:00 amMDW - CHO
1 stop4h 18mDelta
Deal found 1/7$175
This Delta deal was found by Cheapflights users on 1/7. 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 1/297:00 amCHO - ORD
1 stop7h 26mDelta
Sun 2/15:30 amORD - CHO
1 stop4h 48mDelta
Deal found 1/7$175
This Delta deal was found by Cheapflights users on 1/7. 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 3/45:28 pmCHO - ORD
1 stop7h 28mDelta
Mon 3/92:40 pmORD - CHO
1 stop6h 57mDelta
Deal found 1/7$195
This United Airlines deal was found by Cheapflights users on 1/8. 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 2/62:17 pmCHO - ORD
Nonstop2h 16mUnited Airlines
Tue 2/1010:35 amORD - CHO
Nonstop2h 07mUnited Airlines
Deal found 1/8$209
This Delta deal was found by Cheapflights users on 1/8. 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 4/256:00 amCHO - MDW
1 stop4h 56mDelta
Thu 4/306:30 amMDW - CHO
1 stop6h 19mDelta
Deal found 1/8$217
This Delta deal was found by Cheapflights users on 1/8. 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 1/223:02 pmCHO - ORD
1 stop6h 58mDelta
Thu 1/297:05 amORD - CHO
1 stop6h 07mDelta
Deal found 1/8$217
This Delta deal was found by Cheapflights users on 1/8. 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 1/2911:58 amCHO - MDW
1 stop6h 31mDelta
Mon 2/26:00 amMDW - CHO
1 stop7h 12mDelta
Deal found 1/8$222
This Delta deal was found by Cheapflights users on 1/8. 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 2/226:00 amCHO - ORD
1 stop5h 14mDelta
Sun 3/15:25 amORD - CHO
1 stop4h 45mDelta
Deal found 1/8$222
This Delta deal was found by Cheapflights users on 1/7. 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 2/127:00 amCHO - ORD
1 stop7h 23mDelta
Sun 2/155:25 amORD - CHO
1 stop4h 45mDelta
Deal found 1/7$227
This United Airlines deal was found by Cheapflights users on 1/7. 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 2/125:38 pmCHO - ORD
Nonstop2h 12mUnited Airlines
Sun 2/151:02 pmORD - CHO
1 stop4h 45mUnited Airlines
Deal found 1/7$228

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 January 8, 2026.
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 - MDW

CHOMDW

Charlottesville Albemarle

Fri 2/6

6:00 am-9:53 am

1 stop4h 53m

Chicago Midway

Tue 2/10

6:00 am-2:12 pm

1 stop7h 12m

$165

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sat 2/14

4:00 pm-10:31 pm

1 stop7h 31m

Chicago Midway

Wed 2/18

6:00 am-1:46 pm

1 stop6h 46m

$165

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Fri 1/30

6:00 am-9:53 am

1 stop4h 53m

Chicago Midway

Sun 2/1

6:00 am-11:18 am

1 stop4h 18m

$175

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 1/29

11:58 am-5:29 pm

1 stop6h 31m

Chicago Midway

Sun 2/1

6:00 am-11:18 am

1 stop4h 18m

$175

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 1/29

7:00 am-1:26 pm

1 stop7h 26m

Chicago O'Hare Intl

Mon 2/2

6:00 am-1:54 pm

1 stop6h 54m

$175

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 3/4

5:28 pm-11:56 pm

1 stop7h 28m

Chicago O'Hare Intl

Mon 3/9

2:40 pm-10:37 pm

1 stop6h 57m

$195

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 5/20

5:40 pm-6:38 pm

Nonstop1h 58m

Chicago O'Hare Intl

Sun 5/24

10:35 am-1:31 pm

Nonstop1h 56m

$209

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Sat 4/25

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Thu 4/30

6:30 am-1:49 pm

1 stop6h 19m

$217

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 2/6

2:17 pm-3:33 pm

Nonstop2h 16m

Chicago O'Hare Intl

Mon 2/9

2:35 pm-7:44 pm

1 stop4h 09m

$219

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Sun 2/22

6:00 am-10:14 am

1 stop5h 14m

Chicago O'Hare Intl

Sun 3/1

5:25 am-11:10 am

1 stop4h 45m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/8

Showing 1-10 of 36 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 January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Charlottesville-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 January 2, 2026.

To ensure you get the cheapest price possible for a flight from Charlottesville to Chicago, you should look to book at least 24 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, March is the cheapest month in which you can book a flight from Charlottesville to Chicago (average of $48). Flying from Charlottesville to Chicago in June is currently the most expensive (average of $133). 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 January 8, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 26% 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 January 8, 2026.

The most flights from CHO to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 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 January 8, 2026.
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
9,139 reviews

Overall

7.4

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
United Airlines
7.4
Good
9,139 reviews
United Airlines
7.4
Good
9,139 reviews

Overall

7.4

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
American Airlines
7.2
Good
11,095 reviews
United Airlines
7.4
Good
9,139 reviews

Overall

7.4

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.

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 4 daily outbound flights to Chicago from 2 different airlines.

  • How long is the flight from Charlottesville to Chicago?

    For as low as $209, Delta 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 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 Air New Zealand (55%), SkyWest Airlines (45%) or United Airlines (45%) 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 $769 for a flight from Charlottesville to Chicago. The cheapest flight overall is $188 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, March is the cheapest month in which you can book a flight from Charlottesville to Chicago (average of $48). Flying from Charlottesville to Chicago in June is currently the most expensive (average of $133). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$209Average$380FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$228Average$293FlexibilityNo cancel feeOn-time71%

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