$99 Cheap Flights from Charlottesville (CHO) to Chicago (ORD)

View $99 flight on Tue, Oct 7, 2025Opens in a new window

Popular airlines from Charlottesville-Albemarle Airport (CHO) to Chicago O'Hare Intl. Airport (ORD)

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Charlottesville to Chicago (CHO-ORD)

Prices were available within the past 7 days and start at $99 for one-way flights and $179 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Sep 13 - Sat, Dec 13
CHO
Charlottesville
ORD
Chicago
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 13 from Charlottesville to Chicago, returning Sat, Dec 13, priced at $179 found 2 days ago
Delta
Wed, Oct 8 - Sat, Oct 25
CHO
Charlottesville
ORD
Chicago
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Oct 8 from Charlottesville to Chicago, returning Sat, Oct 25, priced at $197 found 5 days ago
American Airlines
Thu, Sep 18 - Mon, Sep 29
CHO
Charlottesville
ORD
Chicago
$209 Roundtrip, found 5 days ago
$209
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Sep 18 from Charlottesville to Chicago, returning Mon, Sep 29, priced at $209 found 5 days ago
Delta
Wed, Oct 8 - Sat, Oct 18
CHO
Charlottesville
ORD
Chicago
$213 Roundtrip, found 5 days ago
$213
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Oct 8 from Charlottesville to Chicago, returning Sat, Oct 18, priced at $213 found 5 days ago
American Airlines
Sat, Sep 13 - Sat, Dec 13
CHO
Charlottesville
ORD
Chicago
$214 Roundtrip, found 2 days ago
$214
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 13 from Charlottesville to Chicago, returning Sat, Dec 13, priced at $214 found 2 days ago
American Airlines
Sat, Sep 20 - Tue, Sep 30
CHO
Charlottesville
ORD
Chicago
$219 Roundtrip, found 5 days ago
$219
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Sep 20 from Charlottesville to Chicago, returning Tue, Sep 30, priced at $219 found 5 days ago
United
Thu, Sep 4 - Mon, Sep 8
CHO
Charlottesville
ORD
Chicago
$219 Roundtrip, found 3 hours ago
$219
Roundtrip
found 3 hours ago
Select United flight, departing Thu, Sep 4 from Charlottesville to Chicago, returning Mon, Sep 8, priced at $219 found 3 hours ago
American Airlines
Sat, Sep 6 - Sun, Sep 7
CHO
Charlottesville
ORD
Chicago
$229 Roundtrip, just found
$229
Roundtrip
just found
Select American Airlines flight, departing Sat, Sep 6 from Charlottesville to Chicago, returning Sun, Sep 7, priced at $229 just found
United
Fri, Sep 5 - Mon, Sep 8
CHO
Charlottesville
ORD
Chicago
$239 Roundtrip, found 6 hours ago
$239
Roundtrip
found 6 hours ago
Select United flight, departing Fri, Sep 5 from Charlottesville to Chicago, returning Mon, Sep 8, priced at $239 found 6 hours ago
United
Thu, Aug 21 - Tue, Aug 26
CHO
Charlottesville
ORD
Chicago
$240 Roundtrip, found 2 days ago
$240
Roundtrip
found 2 days ago
Select United flight, departing Thu, Aug 21 from Charlottesville to Chicago, returning Tue, Aug 26, priced at $240 found 2 days ago

Find the cheapest month to fly from Charlottesville (CHO) to Chicago (ORD)

September is typically the cheapest month to fly

From $199 - $516 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $619
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $619
Flights from Charlottesville (CHO) to Chicago (ORD)
Origin airport
Charlottesville-Albemarle
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$178
Distance
565 mi
Average flight time
1 hour 5 mins

Charlottesville to Chicago Flights

The cheapest times to fly from Charlottesville to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Charlottesville to Chicago are during the month of September. You can find some of the cheapest flights from Charlottesville to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Charlottesville to Chicago

Sunday is one of the best days to book for cheap flights from Charlottesville to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Charlottesville to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Charlottesville to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $99 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Charlottesville to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Charlottesville to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD) cost?
You can book cheap return fares starting at $279 from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving CHO on August 16 2025 and touching down at ORD. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from CHO to ORD?
The cheapest flights from CHO to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD)?
You can travel nonstop from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD) on a United Airlines flight.
What is the cheapest airline that flies from CHO to ORD?
With fares starting at $224 for a one-way journey from CHO to ORD, United is currently the cheapest airline flying this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from CHO on September 26 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD)?
Every day on average, 2 nonstop flights operate from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD). Select the departure date that fits your schedule best.
What are the most popular departure times for flights from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD)?
The 10 AM departures from CHO to ORD are the top choice for many travelers. These flights can come with a higher price due to their popularity. If you want to save on your trip, book during off-peak hours.
What day of the week has the most flights from CHO to ORD?
Friday offers the most flights from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD). Consider traveling on this day and you'll have a greater chance of finding a departure that fits your schedule.
What is the earliest flight from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD)?
The first flight of the day taking off from Charlottesville-Albemarle Airport (CHO) is at around 10:15AM UTC-5. Board this plane and you'll touch down at O'Hare Intl. Airport (ORD) at approximately 11:20AM UTC-6. The entire trip takes 2h 5m.
How long does it take to fly from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD)?
Flights from CHO to ORD have an average travel time of 2 hours and 5 minutes. The distance between these two airports is 570 mi.
What airline has the least delays from CHO to ORD?
United Airlines has the best performance for on-time direct flights from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD), with an on-time rating of 82%. Use the Expedia App to view your flight status before you head off and get real-time updates about any changes.
What is the best time to fly from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD)?
To reach O'Hare Intl. Airport (ORD) on time, opt for a flight that leaves from Charlottesville-Albemarle Airport (CHO) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Charlottesville-Albemarle Airport (CHO)?
If you're boarding a direct flight from Charlottesville-Albemarle Airport (CHO) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute bookings from CHO to ORD are usually more expensive. For the lowest rates, start searching for flights early. That being said, if you're flexible with your travel plans, you may land a cheap ticket right before your journey.
Is it cheaper to book a CHO to ORD flight and hotel package?
Compared with arranging hotels and flights separately, booking a CHO to ORD flight and hotel package with Expedia could result in significant savings. What's more, having everything in one easy place will take the hassle out of travel planning. Simply pick your flights and select from our wide range of stays, then personalize your trip with other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Charlottesville-Albemarle Airport (CHO) to O'Hare Intl. Airport (ORD)?
In most instances, you can modify or cancel your CHO to ORD flight. However, additional fees may apply, especially if your booking was made over 24 hours ago. Check your itinerary for the airline's fees and policies on flight changes, or if you need more details, visit our Customer Service portal.

Explore a world of travel with Expedia

Chicago nearby Airports

Chicago

Charlottesville to Midway Intl.
$196.37
Charlottesville nearby Airports

Weyers Cave

Shenandoah Valley Regional to Chicago
$292.17
*Available to One Key members.