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$194+ 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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — CHI
Mar 30 — Apr 61
Mon 3/30
Mon 4/6
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 Wednesday

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 February 28, 2026.

This Delta deal was found by Cheapflights users on 2/25. 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 8/63:05 pm
CHO
-
ORD
1 stop6h 13m
Delta
Mon 8/108:15 am
ORD
-
CHO
1 stop7h 34m
Delta
Deal found 2/25$249
This Delta deal was found by Cheapflights users on 2/24. 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 4/175:54 pm
CHO
-
MDW
1 stop5h 34m
Delta
Sat 4/1810:41 am
MDW
-
CHO
1 stop4h 44m
Delta
Deal found 2/24$258
This United Airlines deal was found by Cheapflights users on 2/25. 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 4/108:25 pm
CHO
-
ORD
1 stop4h 18m
United Airlines
Sun 4/128:45 am
ORD
-
CHO
1 stop4h 08m
United Airlines
Deal found 2/25$258
This American Airlines deal was found by Cheapflights users on 2/24. 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 5/88:10 pm
CHO
-
ORD
1 stop4h 44m
American Airlines
Tue 8/255:20 am
ORD
-
CHO
1 stop6h 10m
American Airlines
Deal found 2/24$259
This United Airlines deal was found by Cheapflights users on 2/24. 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 4/92:49 pm
CHO
-
ORD
Nonstop2h 11m
United Airlines
Sun 4/126:55 am
ORD
-
CHO
Nonstop2h 05m
United Airlines
Deal found 2/24$260
This United Airlines deal was found by Cheapflights users on 2/25. 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 4/38:20 am
CHO
-
ORD
Nonstop2h 11m
United Airlines
Sat 4/411:10 am
ORD
-
CHO
Nonstop2h 00m
United Airlines
Deal found 2/25$264
This United Airlines deal was found by Cheapflights users on 2/26. 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.
Sun 3/158:29 pm
CHO
-
ORD
1 stop4h 15m
United Airlines
Sun 3/227:10 am
ORD
-
CHO
Nonstop1h 59m
United Airlines
Deal found 2/26$268
This American Airlines deal was found by Cheapflights users on 2/24. 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 3/187:57 pm
CHO
-
ORD
1 stop5h 09m
American Airlines
Mon 3/236:44 pm
ORD
-
CHO
1 stop4h 11m
American Airlines
Deal found 2/24$269
This American Airlines deal was found by Cheapflights users on 2/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:10 pm
CHO
-
ORD
1 stop4h 44m
American Airlines
Sat 8/226:25 pm
ORD
-
CHO
1 stop4h 47m
American Airlines
Deal found 2/27$274
This United Airlines deal was found by Cheapflights users on 2/24. 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.
Tue 3/316:20 am
CHO
-
ORD
1 stop4h 18m
United Airlines
Sat 4/49:35 pm
ORD
-
CHO
Nonstop2h 03m
United Airlines
Deal found 2/24$279
This United Airlines deal was found by Cheapflights users on 2/27. 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 3/1310:45 am
CHO
-
ORD
Nonstop2h 12m
United Airlines
Sat 3/219:15 pm
ORD
-
CHO
Nonstop1h 54m
United Airlines
Deal found 2/27$280
This United Airlines deal was found by Cheapflights users on 2/27. 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.
Sat 3/76:45 am
CHO
-
ORD
Nonstop2h 12m
United Airlines
Sat 3/147:10 am
ORD
-
CHO
Nonstop1h 59m
United Airlines
Deal found 2/27$284

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 February 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(Delta)

One-way from

$194
(American Airlines)

Popular in

September

Cheapest in

January

Average price

$384

Good round-trip deal

$374 or less

Good one-way deal

$233 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. 10% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 28, 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

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Fri 4/17

5:54 pm-10:28 pm

1 stop5h 34m

Chicago Midway

Sat 4/18

10:41 am-4:25 pm

1 stop4h 44m

$258

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 8/13

3:05 pm-8:17 pm

1 stop6h 12m

Chicago O'Hare Intl

Sun 8/16

8:15 am-4:49 pm

1 stop7h 34m

$279

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Tue 3/31

6:20 am-9:38 am

1 stop4h 18m

Chicago O'Hare Intl

Sat 4/4

6:01 pm-11:29 pm

1 stop4h 28m

$299

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Thu 4/23

5:54 pm-10:28 pm

1 stop5h 34m

Chicago Midway

Sat 4/25

5:21 pm-10:55 pm

1 stop4h 34m

$304

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 3/13

8:29 pm-11:44 pm

1 stop4h 15m

Chicago O'Hare Intl

Mon 3/23

9:15 pm-12:09 am

Nonstop1h 54m

$309

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Sun 3/15

8:30 am-9:42 am

Nonstop2h 12m

Chicago O'Hare Intl

Mon 3/23

9:15 pm-12:09 am

Nonstop1h 54m

$324

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 5/8

8:23 pm-11:44 pm

1 stop4h 21m

Chicago O'Hare Intl

Sat 8/22

7:15 am-10:11 am

Nonstop1h 56m

$344

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 6/5

6:30 am-7:42 am

Nonstop2h 12m

Chicago O'Hare Intl

Mon 6/8

6:40 am-9:41 am

Nonstop2h 01m

$345

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 3/13

8:29 pm-11:44 pm

1 stop4h 15m

Chicago O'Hare Intl

Mon 3/16

7:10 am-10:09 am

Nonstop1h 59m

$349

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 6/17

6:25 am-9:36 am

1 stop4h 11m

Chicago O'Hare Intl

Sun 6/21

6:40 am-9:41 am

Nonstop2h 01m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/24

Showing 1-10 of 45 resultsSorted by cheapest first
1
2
3
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5
  • 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 February 20, 2026.

To ensure you get the cheapest price possible for a flight from Charlottesville to Chicago, you should look to book at least 29 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, January is the cheapest month in which you can book a flight from Charlottesville to Chicago (average of $57). Flying from Charlottesville to Chicago in June is currently the most expensive (average of $134). 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 February 28, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 21% 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 February 28, 2026.

The most flights from CHO to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 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 February 28, 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
9,363 reviews

Overall

7.4

Food

6.6

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,363 reviews
United Airlines
7.4
Good
9,363 reviews

Overall

7.4

Food

6.6

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,367 reviews
United Airlines
7.4
Good
9,363 reviews

Overall

7.4

Food

6.6

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 $299, Delta can have you in Chicago from Charlottesville in 4h 18m. 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 SkyWest Airlines (72%), United Airlines (72%) or Air New Zealand (64%) 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 $741 for a flight from Charlottesville to Chicago. The cheapest flight overall is $168 while the most popular route, (Charlottesville Albemarle - Chicago O'Hare Intl) is currently priced at $199.

  • 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, January is the cheapest month in which you can book a flight from Charlottesville to Chicago (average of $57). Flying from Charlottesville to Chicago in June is currently the most expensive (average of $134). 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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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 February 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$209Average$384FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$228Average$293FlexibilityNo cancel feeOn-time71%

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