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

Cheapflights users have booked flights from Charlottesville to Chicago round-trip from $229. Other airlines that can offer you cheap pricing are American Airlines, from $229, and United Airlines, from $239. You may be able to fly from Charlottesville to Chicago for 36% less than the average price by searching for these airlines.

What are the cheapest airlines to fly from Charlottesville to Chicago one-way?

$224 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $226 and $234, respectively.

What is the cheapest day to fly from Charlottesville to Chicago?

Travelers seeking maximum savings on their Charlottesville to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the cheapest flights from Charlottesville to Chicago?

On average you can expect to pay $899 for a flight from Charlottesville to Chicago. The cheapest flight overall is $243 while the most popular route, (Charlottesville Albemarle - Chicago O'Hare Intl) is currently priced at $229.

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 Republic Airways (100%), United Airlines (85%) or SkyWest Airlines (80%) as they are the most reliable in getting you off to your destination on time.

What is the cheapest day to fly round-trip from Charlottesville to Chicago?

Users have found that leaving on a Tuesday can be a cost-effective option. It’s possible to save up to 52% on your flight compared to booking on days when demand is much higher.

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

Find a great deal and save up to 161% by booking at least 58 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Charlottesville to Chicago within the next two weeks, with the cheapest ticket starting at $269.

What is the cheapest month to fly from Charlottesville to Chicago?

February is one of the best times of the year to fly to Chicago from Charlottesville. Prices for February average $363 per person but you can even find prices for as low as $209. The most expensive prices can be found in the month of November. Opting for a February flight can save you 17% on your journey compared to booking in November

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.

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.

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.

$224+ Flights from Charlottesville to Chicago

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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

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Cheapflights Tip: The best prices from Charlottesville Albemarle to Chicago are usually found in February or July, booked 62 days in advance, depart on a Wednesday or Thursday and return on a Tuesday

Cheap flight deals from Charlottesville to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$229 (Delta)
One-way from	$224 (United Airlines)
Popular in	November
Cheapest in	February
Average price	$375
Good round-trip deal	$373 or less
Good one-way deal	$276 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. 4% potential increase in price ($18 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 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 April 17, 2025.

Fri 5/302:59 pmCHO - MDW

1 stop7h 28mDelta

Mon 6/26:00 amMDW - CHO

1 stop7h 14mDelta

Deal found 4/17

$229

Wed 6/1112:00 pmCHO - ORD

1 stop6h 52mDelta

Sun 6/155:35 amORD - CHO

1 stop4h 18mDelta

Deal found 4/17

$229

Thu 5/16:45 amCHO - ORD

Nonstop2h 08mUnited Airlines

Mon 5/54:25 pmORD - CHO

1 stop6h 05mUnited Airlines

Deal found 4/17

$239

Thu 6/198:07 pmCHO - ORD

1 stop4h 50mAmerican Airlines

Sun 6/225:29 amORD - CHO

1 stop6h 06mAmerican Airlines

Deal found 4/17

$359

Best flights from Charlottesville to Chicago
Discover carefully curated flight deals from Charlottesville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2025.

Fri 5/302:59 pmCHO - MDW

1 stop7h 28mDelta

Mon 6/26:00 amMDW - CHO

1 stop7h 14mDelta

Deal found 4/17

$229

Fri 5/308:24 pmCHO - ORD

1 stop4h 47mAmerican Airlines

Mon 6/25:00 amORD - CHO

1 stop6h 53mAmerican Airlines

Deal found 4/17

$229

Thu 5/16:45 amCHO - ORD

Nonstop2h 08mUnited Airlines

Mon 5/54:25 pmORD - CHO

1 stop6h 05mUnited Airlines

Deal found 4/17

$239

Thu 5/111:30 amCHO - ORD

1 stop7h 53mDelta

Sat 5/311:15 amORD - CHO

1 stop4h 45mDelta

Deal found 4/17

$249

Last-minute flights from Charlottesville to Chicago
Discover last-minute flight deals from Charlottesville to Chicago. Data last updated April 17, 2025 and is based on user searches.

Sat 4/265:40 pmCHO - ORD

Nonstop2h 08mUnited Airlines

Sun 4/277:15 amORD - CHO

Nonstop2h 00mUnited Airlines

Deal found 4/17

$289

Sat 4/266:15 amCHO - ORD

1 stop5h 21mAmerican Airlines

Sun 4/275:10 amORD - CHO

1 stop4h 13mAmerican Airlines

Deal found 4/17

$394

Sat 4/265:40 pmCHO - MDW

1 stop5h 42mDelta

Sun 4/276:04 amMDW - CHO

1 stop5h 46mDelta

Deal found 4/17

$534

Thu 5/15:47 pmCHO - ORD

Nonstop2h 08mUnited Airlines

Mon 5/57:10 amORD - CHO

Nonstop2h 00mUnited Airlines

Deal found 4/17

$229

Thu 5/111:30 amCHO - ORD

1 stop7h 53mDelta

Sat 5/311:15 amORD - CHO

1 stop4h 45mDelta

Deal found 4/17

$249

Fri 5/302:59 pmCHO - MDW

1 stop7h 28mDelta

Mon 6/26:00 amMDW - CHO

1 stop7h 14mDelta

Deal found 4/17

$229

One-way flights from Charlottesville to Chicago
Search for one-way flight options from Charlottesville to Chicago. Find affordable one-way fares based on user searches. Data last updated April 17, 2025.

Tue 5/206:45 amCHO - ORD

Nonstop2h 08mUnited Airlines

Deal found 4/16

$224

Fri 7/43:06 pmCHO - ORD

1 stop8h 39mAmerican Airlines

Deal found 4/16

$226

Fri 7/45:40 pmCHO - MDW

1 stop5h 05mDelta

Deal found 4/17

$234

Sat 6/145:40 pmCHO - ORD

1 stop7h 19mDelta

Deal found 4/17

$234

Cheapflights Fare Finder

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 5/30

2:59 pm-9:27 pm

1 stop7h 28m

Chicago Midway

Mon 6/2

6:00 am-2:14 pm

1 stop7h 14m

$229

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 6/11

12:00 pm-5:52 pm

1 stop6h 52m

Chicago O'Hare Intl

Sun 6/15

5:35 am-10:53 am

1 stop4h 18m

$229

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 5/1

6:45 am-7:53 am

Nonstop2h 08m

Chicago O'Hare Intl

Mon 5/5

4:25 pm-11:30 pm

1 stop6h 05m

$239

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Thu 6/19

8:07 pm-11:57 pm

1 stop4h 50m

Chicago O'Hare Intl

Sun 6/22

5:29 am-12:35 pm

1 stop6h 06m

$359

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 7/4

3:06 pm-10:45 pm

1 stop8h 39m

$226

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Fri 7/4

5:40 pm-9:45 pm

1 stop5h 05m

$234

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Sat 6/14

5:40 pm-11:59 pm

1 stop7h 19m

$234

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 7/4

6:10 am-2:55 pm

2 stops9h 45m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Compare providers for flights from Charlottesville to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Charlottesville to Chicago in April.

Provider	Price Accuracy	Trust Score*
eDreams	Price Accuracy3 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*2 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?

To ensure you get the cheapest price possible for a flight from Charlottesville to Chicago, you should look to book at least 57 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?

Unlike in the morning, when flights are generally more expensive, you can save up to 3% on flights from Charlottesville to Chicago by exploring options for tickets at noon.

Weekly flight availability from Charlottesville to Chicago

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).

Rainfall in Chicago by month

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Charlottesville to Chicago, such as Delta, United Airlines and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,917 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta

8.0

Very good

7,917 reviews

Delta

8.0

Very good

7,917 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines

7.4

Good

8,667 reviews

Delta

8.0

Very good

7,917 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,917 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

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.
What are the cheapest airlines flying from Charlottesville to Chicago round-trip?
Cheapflights users have booked flights from Charlottesville to Chicago round-trip from $229. Other airlines that can offer you cheap pricing are American Airlines, from $229, and United Airlines, from $239. You may be able to fly from Charlottesville to Chicago for 36% less than the average price by searching for these airlines.
What are the cheapest airlines to fly from Charlottesville to Chicago one-way?
$224 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $226 and $234, respectively.
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 Republic Airways (100%), United Airlines (85%) or SkyWest Airlines (80%) 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 $899 for a flight from Charlottesville to Chicago. The cheapest flight overall is $243 while the most popular route, (Charlottesville Albemarle - Chicago O'Hare Intl) is currently priced at $229.
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

Merrillville

Hammond

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Porter

Lansing

Valparaiso

Chesterton

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Top 2 airlines flying from Charlottesville to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$148	Average$316	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$219	Average$379	FlexibilityNo cancel fee	On-time69%

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$224+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Charlottesville to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Charlottesville Albemarle to Chicago are usually found in February or July, booked 62 days in advance, depart on a Wednesday or Thursday and return on a Tuesday

Cheap flight deals from Charlottesville to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Charlottesville to Chicago

Cheapest flights from Charlottesville to ChicagoExplore 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 April 17, 2025.

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 April 17, 2025.

Cheapflights Fare Finder

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

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 April.

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.

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 April 11, 2025.

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

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 April 17, 2025.

Weekly flight availability from Charlottesville to Chicago

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Charlottesville to Chicago, such as Delta, United Airlines and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

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?

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

What are the cheapest airlines to fly from Charlottesville to Chicago one-way?

What are the most reliable airlines from Charlottesville to Chicago?

What are the cheapest flights from Charlottesville to Chicago?

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

How can I find direct flights from Charlottesville to Chicago?

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

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

Traveling to a place near Charlottesville?

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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.

Top 2 airlines flying from Charlottesville to Chicago

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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 April 17, 2025.