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$304 Cheap Flights from Charlottesville (CHO) to Chicago (MDW)

View $304 flight on Fri, Dec 4, 2026Opens 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 $304 for one-way flights and $369 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Dec 4 - Wed, Dec 9
CHO
Charlottesville
MDW
Chicago
$369 Roundtrip, found 4 hours ago
$369
Roundtrip
found 4 hours ago
Select Delta flight, departing Fri, Dec 4 from Charlottesville to Chicago, returning Wed, Dec 9, priced at $369 found 4 hours ago
Delta
Mon, Mar 1 - Tue, Mar 30
CHO
Charlottesville
MDW
Chicago
$389 Roundtrip, found 15 hours ago
$389
Roundtrip
found 15 hours ago
Select Delta flight, departing Mon, Mar 1 from Charlottesville to Chicago, returning Tue, Mar 30, priced at $389 found 15 hours ago
Delta
Fri, Apr 30 - Mon, May 3
CHO
Charlottesville
MDW
Chicago
$409 Roundtrip, found 3 days ago
$409
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Apr 30 from Charlottesville to Chicago, returning Mon, May 3, priced at $409 found 3 days ago
Delta
Sat, Feb 13 - Tue, Feb 16
CHO
Charlottesville
MDW
Chicago
$416 Roundtrip, found 1 day ago
$416
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Feb 13 from Charlottesville to Chicago, returning Tue, Feb 16, priced at $416 found 1 day ago
Delta
Thu, Dec 17 - Sun, Dec 20
CHO
Charlottesville
MDW
Chicago
$419 Roundtrip, found 6 days ago
$419
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Dec 17 from Charlottesville to Chicago, returning Sun, Dec 20, priced at $419 found 6 days ago
Delta
Thu, May 6 - Sun, May 9
CHO
Charlottesville
MDW
Chicago
$424 Roundtrip, found 2 days ago
$424
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, May 6 from Charlottesville to Chicago, returning Sun, May 9, priced at $424 found 2 days ago
Delta
Sun, Dec 13 - Tue, Jan 19
CHO
Charlottesville
MDW
Chicago
$444 Roundtrip, found 6 hours ago
$444
Roundtrip
found 6 hours ago
Select Delta flight, departing Sun, Dec 13 from Charlottesville to Chicago, returning Tue, Jan 19, priced at $444 found 6 hours ago
Delta
Wed, May 5 - Mon, May 10
CHO
Charlottesville
MDW
Chicago
$445 Roundtrip, found 1 day ago
$445
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 5 from Charlottesville to Chicago, returning Mon, May 10, priced at $445 found 1 day ago
Delta
Fri, Dec 4 - Sun, Dec 6
CHO
Charlottesville
MDW
Chicago
$454 Roundtrip, found 4 days ago
$454
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Dec 4 from Charlottesville to Chicago, returning Sun, Dec 6, priced at $454 found 4 days ago
Delta
Sun, Dec 13 - Tue, Jan 19
CHO
Charlottesville
MDW
Chicago
$464 Roundtrip, found 6 hours ago
$464
Roundtrip
found 6 hours ago
Select Delta flight, departing Sun, Dec 13 from Charlottesville to Chicago, returning Tue, Jan 19, priced at $464 found 6 hours 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 $484
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $484

Frequently asked questions

How much does a flight from Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $304 and cheap return flights from $369 Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights typically cost between $239 and $1073, and return flights often range between $368 and $1436. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from CHO to MDW is December when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.)?
Enter CHO to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.)?
Delta is one of the cheapest airlines offering connecting flights from Charlottesville, VA (CHO) to Chicago, IL (MDW) starting from around $303.37. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Charlottesville-Albemarle Airport (CHO) to Midway International Airport (MDW) usually departs at around 5:35 AM, operated by Delta. This seasonal service is available in October and November, giving you an early start to your day in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Charlottesville-Albemarle (CHO) to Midway Intl. (MDW) are in the early morning, from 3am to 6am. About 32% of passengers prefer this time window. Delta Airlines offers flights during this period. This timing is favored as it allows you to arrive in Chicago with a full day ahead of you.
How long does it take to fly from Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.)?
Flying from CHO to MDW with a connection usually takes about 7 hours, traveling roughly 553 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the CHO to MDW route with Delta Air Lines.
How do I earn miles on a Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Keyâ„¢, you can also earn OneKeyCashâ„¢* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Charlottesville-Albemarle (CHO)?
When traveling from Charlottesville-Albemarle (CHO) to Chicago, you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD). Some flights may connect through major hubs like Washington Dulles Intl. (IAD), LaGuardia (LGA) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Charlottesville, VA (CHO-Charlottesville-Albemarle) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Charlottesville-Albemarle
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$368
Distance
552 mi

Book with confidence

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 December. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $304 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.

 

Charlottesville to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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