What is the cheapest airline that flies from Charlottesville Albemarle to Chicago?

Delta, American Airlines, and United Airlines are the most popular carriers operating from Charlottesville Albemarle to Chicago

Which layover airport has the shortest travel time from Charlottesville to Chicago?

Flights connecting via New York (LGA) have the shortest average one-way travel time: 4h 48m.

Which layover airport offers the lowest fares from Charlottesville to Chicago?

Flights via Charlotte (CLT) offer the lowest average round-trip price of $248.

Which airport is the most popular layover for flights between Charlottesville and Chicago?

New York (LGA) was the most common stop: 83% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest connection time from Charlottesville to Chicago?

New York (LGA) has the shortest average layover time for this route: 0h 37m.

How many flights depart from Charlottesville to Chicago on average per day?

The number of flights available between Charlottesville and Chicago is 3 per day as of August 2025. The most frequent departure time is 7:00AM, with 50% of daily flights leaving at noon.

How many flights depart from Charlottesville to Chicago on average per week?

26 flights are operational weekly from Charlottesville to Chicago as of August 2025. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.

What airlines fly to Chicago?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Charlottesville according to our data. United Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Charlottesville Albemarle Airport to Chicago?

Prices for flights from Charlottesville Albemarle Airport to Chicago were last updated today.

How many operators does momondo search for flights from Charlottesville Albemarle Airport to Chicago?

There are 2 operators available for flights from Charlottesville Albemarle Airport to Chicago as of August 2025.

How old do you have to be to fly from Charlottesville Albemarle Airport to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Charlottesville Albemarle Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$125 Cheap Flights from Charlottesville to Chicago in 2025

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Find the cheapest flights from Charlottesville to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:00 am - 10:03 amCHO-ORD

5h 03m1 stop

7:00 am - 2:24 pmORD-CHO

6h 24m1 stop

$224Delta

Find Deal

Sat, Nov 15 - Sat, Dec 6

4:05 pm - 9:46 pmCHO-MDW

6h 41m1 stop

6:00 am - 2:26 pmMDW-CHO

7h 26m1 stop

$229Delta

Find Deal

Sat, Jan 17 - Tue, Jan 20

1:18 pm - 6:34 pmCHO-ORD

6h 16m1 stop

9:51 am - 3:59 pmORD-CHO

5h 08m1 stop

$229American Airlines

Find Deal

Sat, Sep 13 - Wed, Sep 17

8:56 am - 2:13 pmCHO-ORD

6h 17m1 stop

5:00 am - 11:47 amORD-CHO

5h 47m1 stop

$239American Airlines

Find Deal

Sat, Nov 1 - Mon, Nov 3

6:51 pm - 11:12 pmCHO-ORD

5h 21m1 stop

5:00 am - 10:48 amORD-CHO

4h 48m1 stop

$249American Airlines

Find Deal

Fri, Sep 19 - Sun, Sep 21

5:41 pm - 6:47 pmCHO-ORD

2h 06mnonstop

6:15 pm - 9:26 pmORD-CHO

2h 11mnonstop

$259United Airlines

Find Deal

Wed, Aug 27 - Sun, Aug 31

2:35 pm - 6:25 pmCHO-ORD

4h 50m1 stop

6:15 pm - 9:26 pmORD-CHO

2h 11mnonstop

$269United Airlines

Find Deal

Wed, Aug 27 - Sun, Aug 31

6:01 pm - 10:14 pmCHO-MDW

5h 13m1 stop

4:23 pm - 10:49 pmMDW-CHO

5h 26m1 stop

$269Delta

Find Deal

Tue, Oct 7 - Sat, Oct 11

5:41 pm - 6:47 pmCHO-ORD

2h 06mnonstop

9:31 pm - 9:47 amORD-CHO

11h 16m2 stops

$274United Airlines

Find Deal

Sat, Aug 30 - Sat, Aug 30

8:29 pm - 11:15 pmCHO-ORD

3h 46m1 stop

8:45 am - 11:57 amORD-CHO

2h 12mnonstop

$289United Airlines

Find Deal

Sat, Sep 27 - Sat, Oct 4

United Airlines flights from Charlottesville to Chicago

Our best United Airlines deals on Charlottesville to Chicago flight tickets

United Airlines

Aug 28

CHO7:00 amCharlottesville Albemarle

2h 05m

ORD8:05 amChicago O'Hare Intl

Sep 1

ORD7:19 amChicago O'Hare Intl

2h 05m

CHO10:24 amCharlottesville Albemarle

$229

Find similar

United Airlines

Aug 27

CHO5:41 pmCharlottesville Albemarle

2h 06m

ORD6:47 pmChicago O'Hare Intl

Aug 31

ORD6:15 pmChicago O'Hare Intl

2h 11m

CHO9:26 pmCharlottesville Albemarle

$259

Find similar

United Airlines

Aug 27

CHO2:35 pmCharlottesville Albemarle

4h 50m

1 stop

ORD6:25 pmChicago O'Hare Intl

Aug 31

ORD6:15 pmChicago O'Hare Intl

2h 11m

CHO9:26 pmCharlottesville Albemarle

$269

Find similar

American Airlines flights from Charlottesville to Chicago

Our best American Airlines deals on Charlottesville to Chicago flight tickets

American Airlines

Sep 13

CHO1:18 pmCharlottesville Albemarle

6h 16m

1 stop

ORD6:34 pmChicago O'Hare Intl

Sep 17

ORD9:51 amChicago O'Hare Intl

5h 08m

1 stop

CHO3:59 pmCharlottesville Albemarle

$229

Find similar

American Airlines

Nov 1

CHO8:56 amCharlottesville Albemarle

6h 17m

1 stop

ORD2:13 pmChicago O'Hare Intl

Nov 3

ORD5:00 amChicago O'Hare Intl

5h 47m

1 stop

CHO11:47 amCharlottesville Albemarle

$239

Find similar

American Airlines

Aug 27

CHO2:17 pmCharlottesville Albemarle

5h 12m

1 stop

ORD6:29 pmChicago O'Hare Intl

Aug 30

ORD9:20 amChicago O'Hare Intl

7h 23m

1 stop

CHO5:43 pmCharlottesville Albemarle

$249

Find similar

Fly from

Fly to

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 - 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

Sat 9/13

1:18 pm-6:34 pm

1 stop6h 16m

Chicago O'Hare Intl

Wed 9/17

9:51 am-3:59 pm

1 stop5h 08m

$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

$239

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Fri 9/19

6:51 pm-11:12 pm

1 stop5h 21m

Chicago O'Hare Intl

Sun 9/21

5:00 am-10:48 am

1 stop4h 48m

$249

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 8/27

5:41 pm-6:47 pm

Nonstop2h 06m

Chicago O'Hare Intl

Sun 8/31

6:15 pm-9:26 pm

Nonstop2h 11m

$259

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Wed 8/27

2:35 pm-6:25 pm

1 stop4h 50m

Chicago O'Hare Intl

Sun 8/31

6:15 pm-9:26 pm

Nonstop2h 11m

$269

CharlottesvilleChicago

CHO - MDW

CHOMDW

Charlottesville Albemarle

Tue 10/7

6:01 pm-10:14 pm

1 stop5h 13m

Chicago Midway

Sat 10/11

4:23 pm-10:49 pm

1 stop5h 26m

$269

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Sat 8/30

5:41 pm-6:47 pm

Nonstop2h 06m

Chicago O'Hare Intl

Sat 8/30

9:31 pm-9:47 am

2 stops11h 16m

$274

CharlottesvilleChicago

CHO - ORD

CHOORD

Charlottesville Albemarle

Sat 9/27

8:29 pm-11:15 pm

1 stop3h 46m

Chicago O'Hare Intl

Sat 10/4

8:45 am-11:57 am

Nonstop2h 12m

$289

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Charlottesville to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

Other information

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Charlottesville, with most prices found around $280. If you’re not able to fly to Chicago in February, then December is your next best option. Flight prices from Charlottesville to Chicago during December average around $327.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $435. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Charlottesville to Chicago for around $640.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Charlottesville to Chicago during this time can be as low as $476. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $514.

What is the cheapest Charlottesville Albemarle to Chicago flight route?

Fly from Charlottesville Albemarle to Chicago O'Hare Intl for the best Charlottesville Albemarle - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Charlottesville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $401 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Charlottesville for as low as $322 on momondo.

What cabin class options are available on Charlottesville Albemarle to Chicago flights?

There are 4 cabin classes available to choose from on Charlottesville Albemarle to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Charlottesville to Chicago flights?

You could potentially save up to 28% on your flight if you consider stops on a Charlottesville to Chicago flight.

When to book flights from Charlottesville to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Charlottesville to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Charlottesville to Chicago (CHO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Charlottesville to Chicago

Best Price Found	$125
Fastest flight time	2h 05m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Charlottesville in the past 72 hours is $125. The best round-trip flight deal from Charlottesville to Chicago found on momondo in the last 72 hours is $224.

The fastest flight from Charlottesville to Chicago takes 2h 05m

Direct flights go from Charlottesville to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

How far is Charlottesville Albemarle to Chicago by plane?
A flight from Charlottesville Albemarle to Chicago will travel around 551.8 mi. Typically, this will take 2h 05m by plane in normal conditions.
When did momondo last update prices for flights from Charlottesville Albemarle Airport to Chicago?
Prices for flights from Charlottesville Albemarle Airport to Chicago were last updated today.
How many operators does momondo search for flights from Charlottesville Albemarle Airport to Chicago?
There are 2 operators available for flights from Charlottesville Albemarle Airport to Chicago as of August 2025.
How old do you have to be to fly from Charlottesville Albemarle Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Charlottesville Albemarle Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Charlottesville to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Charlottesville to Chicago is Canadair (Bombardier) Regional Jet CRJ-550, representing 56.83% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 12.02%, Canadair (Bombardier) Regional Jet at 3.83%, and Boeing 737 MAX 8 at 2.19%.
What is the most popular airline from Charlottesville to Chicago?
momondo data reveals that the most frequently booked airline on the route from Charlottesville to Chicago is United Airlines, representing 90% of all bookings. The subsequent popular airline is American Airlines at 10%.

Best airlines flying from Charlottesville to Chicago

Compare and see reviews for airlines that fly from Charlottesville to Chicago with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $219	Free Cancellation	Rating 7.4 8,916 reviews		Search United Airlines flights
American Airlines	PriceFrom $228	Free Cancellation	Rating 7.2 10,000 reviews		Search American Airlines flights

United Airlines Flights From Charlottesville to Chicago
United Airlines operates around 13 flights from Charlottesville to Chicago every week. The average price of these flights found in the last 72 hours has been $405, but momondo users have found United Airlines deals from Charlottesville to Chicago from as low as $219 round-trip. United Airlines has been scored 7.4/10 in 8,916 reviews.

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Schererville

Valparaiso

Crown Point

Munster

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Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Charlottesville to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Charlottesville to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Charlottesville to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Charlottesville with this policy.

How can momondo help me find flights from Charlottesville to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Charlottesville to Chicago.

I’m not ready to book a flight from Charlottesville to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Charlottesville. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Cheap flights from Charlottesville to Chicago from $125

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Charlottesville to Chicago departing on 8/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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United Airlines flights from Charlottesville to Chicago

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Our best American Airlines deals on Charlottesville to Chicago flight tickets

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How to get the cheapest flight ticket from Charlottesville to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Charlottesville to Chicago during this time can be as low as $476. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $514.

What is the cheapest Charlottesville Albemarle to Chicago flight route?

Fly from Charlottesville Albemarle to Chicago O'Hare Intl for the best Charlottesville Albemarle - Chicago flight prices

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

What cabin class options are available on Charlottesville Albemarle to Chicago flights?

There are 4 cabin classes available to choose from on Charlottesville Albemarle to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Charlottesville to Chicago flights?

You could potentially save up to 28% on your flight if you consider stops on a Charlottesville to Chicago flight.

What is the cheapest airline that flies from Charlottesville Albemarle to Chicago?

Delta, American Airlines, and United Airlines are the most popular carriers operating from Charlottesville Albemarle to Chicago

What airlines fly to Chicago?

Which airport is the most popular layover for flights between Charlottesville and Chicago?

New York (LGA) was the most common stop: 83% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Charlottesville to Chicago?

Flights via Charlotte (CLT) offer the lowest average round-trip price of $248.

Which layover airport has the shortest travel time from Charlottesville to Chicago?

Flights connecting via New York (LGA) have the shortest average one-way travel time: 4h 48m.

Which layover airport has the shortest connection time from Charlottesville to Chicago?

New York (LGA) has the shortest average layover time for this route: 0h 37m.

How many flights depart from Charlottesville to Chicago on average per day?

The number of flights available between Charlottesville and Chicago is 3 per day as of August 2025. The most frequent departure time is 7:00AM, with 50% of daily flights leaving at noon.

How many flights depart from Charlottesville to Chicago on average per week?

26 flights are operational weekly from Charlottesville to Chicago as of August 2025. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.

When to book flights from Charlottesville to Chicago

Cheap Charlottesville to Chicago (CHO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Charlottesville to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Charlottesville Albemarle to Chicago by plane?

When did momondo last update prices for flights from Charlottesville Albemarle Airport to Chicago?

How many operators does momondo search for flights from Charlottesville Albemarle Airport to Chicago?

How old do you have to be to fly from Charlottesville Albemarle Airport to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Charlottesville to Chicago?

What is the most popular airline from Charlottesville to Chicago?

Best airlines flying from Charlottesville to Chicago

Compare and see reviews for airlines that fly from Charlottesville to Chicago with momondo

United Airlines Flights From Charlottesville to Chicago

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Charlottesville to Chicago?

Can I find flights from Charlottesville to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Charlottesville to Chicago?

I’m not ready to book a flight from Charlottesville to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago