$174 Cheap Flights from Roanoke (ROA) to Chicago (ORD)

View $174 flight on Mon, Jul 13, 2026Opens in a new window

Popular airlines from Roanoke Regional Airport (ROA) to Chicago O'Hare Intl. Airport (ORD)

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

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

Cheap Flights from Roanoke to Chicago (ROA-ORD)

Prices were available within the past 7 days and start at $174 for one-way flights and $269 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, Jul 14 - Sat, Jul 18
ROA
Roanoke
ORD
Chicago
$269 Roundtrip, just found
$269
Roundtrip
just found
Select American Airlines flight, departing Tue, Jul 14 from Roanoke to Chicago, returning Sat, Jul 18, priced at $269 just found
United
Sat, May 23 - Thu, May 28
ROA
Roanoke
ORD
Chicago
$269 Roundtrip, found 1 hour ago
$269
Roundtrip
found 1 hour ago
Select United flight, departing Sat, May 23 from Roanoke to Chicago, returning Thu, May 28, priced at $269 found 1 hour ago
American Airlines
Tue, Jul 14 - Sat, Jul 18
ROA
Roanoke
ORD
Chicago
$279 Roundtrip, just found
$279
Roundtrip
just found
Select American Airlines flight, departing Tue, Jul 14 from Roanoke to Chicago, returning Sat, Jul 18, priced at $279 just found
United
Tue, Jul 14 - Sun, Jul 19
ROA
Roanoke
ORD
Chicago
$289 Roundtrip, found 1 hour ago
$289
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Jul 14 from Roanoke to Chicago, returning Sun, Jul 19, priced at $289 found 1 hour ago
Delta
Tue, Jul 14 - Sat, Jul 18
ROA
Roanoke
ORD
Chicago
$289 Roundtrip, just found
$289
Roundtrip
just found
Select Delta flight, departing Tue, Jul 14 from Roanoke to Chicago, returning Sat, Jul 18, priced at $289 just found
American Airlines
Thu, May 21 - Sun, May 24
ROA
Roanoke
ORD
Chicago
$289 Roundtrip, found 11 hours ago
$289
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Thu, May 21 from Roanoke to Chicago, returning Sun, May 24, priced at $289 found 11 hours ago
American Airlines
Tue, Jul 14 - Sat, Jul 18
ROA
Roanoke
ORD
Chicago
$290 Roundtrip, just found
$290
Roundtrip
just found
Select American Airlines flight, departing Tue, Jul 14 from Roanoke to Chicago, returning Sat, Jul 18, priced at $290 just found
United
Fri, Sep 25 - Wed, Sep 30
ROA
Roanoke
ORD
Chicago
$292 Roundtrip, found 1 hour ago
$292
Roundtrip
found 1 hour ago
Select United flight, departing Fri, Sep 25 from Roanoke to Chicago, returning Wed, Sep 30, priced at $292 found 1 hour ago
United
Wed, Sep 23 - Sun, Sep 27
ROA
Roanoke
ORD
Chicago
$293 Roundtrip, found 2 days ago
$293
Roundtrip
found 2 days ago
Select United flight, departing Wed, Sep 23 from Roanoke to Chicago, returning Sun, Sep 27, priced at $293 found 2 days ago
United
Tue, Jul 14 - Sat, Jul 18
ROA
Roanoke
ORD
Chicago
$297 Roundtrip, just found
$297
Roundtrip
just found
Select United flight, departing Tue, Jul 14 from Roanoke to Chicago, returning Sat, Jul 18, priced at $297 just found

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 $664
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $664

Frequently asked questions

How much does a flight from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights and cheap return flights from $269 Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights typically cost between $231 and $697, and return flights often range between $326 and $1018. 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 Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare 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 Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.)?
February is typically the cheapest month to fly from Roanoke, VA (ROA) to Chicago, IL (ORD), with average return fares around $292. This is about 24% lower than the average price throughout the year, as demand tends to drop after the holiday season. Other cheap months to fly from Roanoke to Chicago include January and August.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.)?
2 airlines operate nonstop service from ROA to ORD:

  • United operates around 26 direct flights from ROA to ORD every week
  • American Airlines operates around 7 direct flights from ROA to ORD every week

What is the cheapest airline that flies from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.)?
United is one of the cheapest airlines offering nonstop flights from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.) with return tickets starting from around $184. This is a convenient option if you prefer a direct flight. 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 Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare 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 airline to fly with from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Roanoke, VA (ROA) to Chicago, IL (ORD) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, United typically offers the lowest fares. American Airlines offers the most daily flights from Roanoke to Chicago, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly from Roanoke (ROA) to Chicago (ORD) is in January or February. January offers return flights for about $292, making it the cheapest month. February is also a good option, as it typically has lower travel demand. These months are ideal for travelers looking for budget-friendly fares and a more relaxed travel experience.*Prices based on flights available on Expedia in the last year.
How many flights per day from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.)?
You can find approximately 5 nonstop flights per day from Roanoke Regional (ROA) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Roanoke Regional Airport (ROA) to O'Hare International Airport (ORD) typically departs at around 5:00 AM, operated by American Airlines. This seasonal service is active in September and October, 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 Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Roanoke Regional (ROA) to O'Hare Intl. (ORD) are in the early morning, from 6am to 9am. About 38% of travelers prefer this time window. Many major carriers, including American Airlines, United, and Delta, provide flights during this time. This is a great option for those wanting to start their day early in Chicago.
How long does it take to fly from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.)?
A nonstop flight from ROA to ORD typically takes around 2 hours 20 minutes, covering approximately 530 miles. Connecting flights on this route usually add 2 hours 40 minutes to your travel time. 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 Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.)?
First class is available on flights from ROA to ORD. First class cabins are available on:

  • Delta Air Lines
  • United Airlines
  • American Airlines

How much is a business class flight from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.)?
A direct, return business class ticket from Roanoke, VA (ROA) to Chicago, IL (ORD) typically costs between $1,040 - $1,321. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare 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 Key™, you can also earn OneKeyCash™* 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 Roanoke Regional (ROA)?
From Roanoke Regional (ROA), you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Charlotte-Douglas Intl. (CLT), Philadelphia Intl. (PHL), 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 Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare 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 Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare 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 Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (ORD-O'Hare 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
Roanoke Regional
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$269
Distance
529 mi
Average flight time
1 hour 12 mins

Book with confidence

Roanoke to Chicago Flights

The cheapest times to fly from Roanoke 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 Roanoke to Chicago are during the month of July. You can find some of the cheapest flights from Roanoke to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Roanoke to Chicago

Sunday is one of the best days to book for cheap flights from Roanoke 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 Roanoke 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 Roanoke to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $174 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 Roanoke 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 Roanoke 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.

 

Roanoke to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

Explore a world of travel with Expedia