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

View $99 flight on Tue, Nov 18, 2025Opens in a new window

Popular airlines from Charlottesville-Albemarle Airport (CHO) to Chicago Midway Airport (MDW)

Cheap Flights from Charlottesville to Chicago (CHO-MDW)

Prices were available within the past 7 days and start at $99 for one-way flights and $213 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Nov 8 - Mon, Nov 10
CHO
Charlottesville
MDW
Chicago
$213 Roundtrip, found 3 days ago
$213
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Nov 8 from Charlottesville to Chicago, returning Mon, Nov 10, priced at $213 found 3 days ago
Delta
Wed, Jan 7 - Sun, Jan 25
CHO
Charlottesville
MDW
Chicago
$217 Roundtrip, found 5 days ago
$217
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Jan 7 from Charlottesville to Chicago, returning Sun, Jan 25, priced at $217 found 5 days ago
Delta
Tue, Dec 9 - Tue, Dec 16
CHO
Charlottesville
MDW
Chicago
$229 Roundtrip, found 3 hours ago
$229
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Dec 9 from Charlottesville to Chicago, returning Tue, Dec 16, priced at $229 found 3 hours ago
Delta
Thu, Oct 23 - Mon, Oct 27
CHO
Charlottesville
MDW
Chicago
$232 Roundtrip, found 4 days ago
$232
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Oct 23 from Charlottesville to Chicago, returning Mon, Oct 27, priced at $232 found 4 days ago
Delta
Thu, Mar 19 - Sat, Apr 4
CHO
Charlottesville
MDW
Chicago
$237 Roundtrip, found 5 days ago
$237
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Mar 19 from Charlottesville to Chicago, returning Sat, Apr 4, priced at $237 found 5 days ago
Delta
Sun, Oct 12 - Sat, Oct 25
CHO
Charlottesville
MDW
Chicago
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Oct 12 from Charlottesville to Chicago, returning Sat, Oct 25, priced at $239 found 1 day ago
Delta
Tue, Nov 4 - Sat, Nov 22
CHO
Charlottesville
MDW
Chicago
$242 Roundtrip, found 5 days ago
$242
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Nov 4 from Charlottesville to Chicago, returning Sat, Nov 22, priced at $242 found 5 days ago
Delta
Thu, Dec 11 - Mon, Dec 15
CHO
Charlottesville
MDW
Chicago
$247 Roundtrip, found 5 days ago
$247
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Dec 11 from Charlottesville to Chicago, returning Mon, Dec 15, priced at $247 found 5 days ago
Delta
Sat, Jan 10 - Tue, Jan 27
CHO
Charlottesville
MDW
Chicago
$257 Roundtrip, found 5 days ago
$257
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jan 10 from Charlottesville to Chicago, returning Tue, Jan 27, priced at $257 found 5 days ago
Delta
Sun, Nov 23 - Wed, Nov 26
CHO
Charlottesville
MDW
Chicago
$267 Roundtrip, found 4 days ago
$267
Roundtrip
found 4 days ago
Select Delta flight, departing Sun, Nov 23 from Charlottesville to Chicago, returning Wed, Nov 26, priced at $267 found 4 days ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $314
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $314
Flights from Charlottesville (CHO) to Chicago (MDW)
Origin airport
Charlottesville-Albemarle
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$212
Distance
552 mi

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 November. 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 Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $99 or cheap return flight from $213 from Charlottesville-Albemarle Airport (CHO) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Charlottesville-Albemarle Airport (CHO) to Midway Intl. Airport (MDW)?
The cheapest month to fly from CHO to MDW is November, when demand is low. Off-peak months are typically when airlines offer lower prices between these airports.
What is the cheapest airline that flies from Charlottesville-Albemarle Airport (CHO) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from CHO to MDW, use Expedia's filter tool. Customize your search based on what matters most to you, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Charlottesville-Albemarle Airport (CHO) to Midway Intl. Airport (MDW)?
There are no daily nonstop flights departing from Charlottesville-Albemarle Airport (CHO) to Midway Intl. Airport (MDW). But you can book flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from CHO to MDW?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can change based on a number of factors, such as the season and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Charlottesville-Albemarle Airport (CHO) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Charlottesville-Albemarle Airport (CHO) to Midway Intl. Airport (MDW) route, aim to fly before 3 PM. Later flights have a 22% higher chance of cancellation.**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 on a direct flight from Charlottesville-Albemarle Airport (CHO) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Charlottesville-Albemarle Airport (CHO) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your trip to book your flight from CHO to MDW often results in higher prices. While you might find some last-minute discounts, there's no guarantee. Keep your travel schedule open for the best chance of snagging a bargain.
Is it cheaper to book a CHO to MDW flight and hotel package?
You can save money by booking a CHO to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. After selecting your ideal accommodations and flights, consider adding extras including tours, car rentals and activities.
Can I cancel or change the date of my flight from Charlottesville-Albemarle Airport (CHO) to Midway Intl. Airport (MDW)?
You can usually cancel or reschedule your CHO to MDW flight. However, for bookings made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more information on our Customer Service portal.

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*Available to One Key members.