$170 Cheap Flights from Roanoke (ROA) to Chicago (ORD)

View $170 flight on Sat, Sep 13, 2025Opens in a new window

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

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Cheap Flights from Roanoke to Chicago (ROA-ORD)

Prices were available within the past 7 days and start at $170 for one-way flights and $209 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Fri, Aug 22 - Mon, Aug 25
ROA
Roanoke
ORD
Chicago
$209 Roundtrip, found 2 hours ago
$209
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Fri, Aug 22 from Roanoke to Chicago, returning Mon, Aug 25, priced at $209 found 2 hours ago
United
Thu, Sep 4 - Mon, Sep 8
ROA
Roanoke
ORD
Chicago
$209 Roundtrip, just found
$209
Roundtrip
just found
Select United flight, departing Thu, Sep 4 from Roanoke to Chicago, returning Mon, Sep 8, priced at $209 just found
United
Thu, Sep 4 - Mon, Sep 8
ROA
Roanoke
ORD
Chicago
$219 Roundtrip, just found
$219
Roundtrip
just found
Select United flight, departing Thu, Sep 4 from Roanoke to Chicago, returning Mon, Sep 8, priced at $219 just found
American Airlines
Sat, Aug 30 - Tue, Sep 2
ROA
Roanoke
ORD
Chicago
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Aug 30 from Roanoke to Chicago, returning Tue, Sep 2, priced at $220 found 1 day ago
United
Fri, Oct 3 - Sun, Oct 5
ROA
Roanoke
ORD
Chicago
$228 Roundtrip, found 12 hours ago
$228
Roundtrip
found 12 hours ago
Select United flight, departing Fri, Oct 3 from Roanoke to Chicago, returning Sun, Oct 5, priced at $228 found 12 hours ago
Delta
Sat, Oct 18 - Sat, Nov 8
ROA
Roanoke
ORD
Chicago
$229 Roundtrip, just found
$229
Roundtrip
just found
Select Delta flight, departing Sat, Oct 18 from Roanoke to Chicago, returning Sat, Nov 8, priced at $229 just found
United
Tue, Aug 19 - Sat, Aug 23
ROA
Roanoke
ORD
Chicago
$229 Roundtrip, just found
$229
Roundtrip
just found
Select United flight, departing Tue, Aug 19 from Roanoke to Chicago, returning Sat, Aug 23, priced at $229 just found
American Airlines
Fri, Nov 7 - Wed, Nov 12
ROA
Roanoke
ORD
Chicago
$230 Roundtrip, found 19 hours ago
$230
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Fri, Nov 7 from Roanoke to Chicago, returning Wed, Nov 12, priced at $230 found 19 hours ago
United
Mon, Nov 3 - Sat, Nov 8
ROA
Roanoke
ORD
Chicago
$237 Roundtrip, found 2 hours ago
$237
Roundtrip
found 2 hours ago
Select United flight, departing Mon, Nov 3 from Roanoke to Chicago, returning Sat, Nov 8, priced at $237 found 2 hours ago
Delta
Sat, Oct 18 - Wed, Nov 5
ROA
Roanoke
ORD
Chicago
$239 Roundtrip, just found
$239
Roundtrip
just found
Select Delta flight, departing Sat, Oct 18 from Roanoke to Chicago, returning Wed, Nov 5, priced at $239 just found

Find the cheapest month to fly from Roanoke (ROA) to Chicago (ORD)

September is typically the cheapest month to fly

From $199 - $447 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. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $239
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $239
Flights from Roanoke (ROA) to Chicago (ORD)
Origin airport
Roanoke Regional
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$209
Distance
529 mi
Average flight time
1 hour 5 mins

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 August. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $170 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.

 

Frequently asked questions

How much does a flight from Roanoke Regional Airport (ROA) to O'Hare Intl. Airport (ORD) cost?
You'll find affordable return tickets from Roanoke Regional Airport (ROA) to O'Hare Intl. Airport (ORD) starting at $209. Grab your seat and be on your way. 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 American Airlines flight leaving ROA on August 19 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 ROA to ORD?
The cheapest flights from ROA 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 Roanoke Regional Airport (ROA) to O'Hare Intl. Airport (ORD)?
You can fly directly from Roanoke Regional Airport (ROA) to O'Hare Intl. Airport (ORD) on a United Airlines flight.
What is the cheapest airline that flies from ROA to ORD?
Jet off from ROA to ORD with United. This airline currently has the cheapest one-way ticket on this route, starting at $224. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ROA on October 15 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from Roanoke Regional Airport (ROA) to O'Hare Intl. Airport (ORD)?
When taking off from Roanoke Regional Airport (ROA), you can pick from an average of 2 daily direct flights to O'Hare Intl. Airport (ORD).
What are the most popular departure times for flights from Roanoke Regional Airport (ROA) to O'Hare Intl. Airport (ORD)?
The 6 AM departures from ROA to ORD see the highest demand. Prices can be higher for these popular slots. If you're looking to save, pick a less crowded time to fly.
What day of the week has the most flights from ROA to ORD?
Depart on a Friday if you're searching for the best choice of flights from Roanoke Regional Airport (ROA) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Roanoke Regional Airport (ROA) to O'Hare Intl. Airport (ORD)?
Roanoke Regional Airport (ROA)'s first flight to O'Hare Intl. Airport (ORD) leaves at approximately 6:30AM UTC-5. With a flight time of 2h 21m, you'll land at around 7:51AM UTC-6.
How long does it take to fly from Roanoke Regional Airport (ROA) to O'Hare Intl. Airport (ORD)?
Flights from ROA to ORD have an average travel time of 2 hours and 17 minutes. The distance between the two is 530 mi.
What is the best time to fly from Roanoke Regional Airport (ROA) to O'Hare Intl. Airport (ORD)?
Select a flight from Roanoke Regional Airport (ROA) to O'Hare Intl. Airport (ORD) that takes off before 3 PM to reduce the likelihood of delays. Later departures have a 22% higher chance of being canceled, on average.**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 Roanoke Regional Airport (ROA)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Roanoke Regional Airport (ROA). Compare your options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Roanoke Regional Airport (ROA) to O'Hare Intl. Airport (ORD) last-minute?
Waiting until right before your break to book a ticket from ROA to ORD often results in higher prices. While you may find some last-minute deals, they aren't always guaranteed. Keep your travel schedule open to boost your chances of landing a bargain.
Is it cheaper to book a ROA to ORD flight and hotel package?
Booking a ROA to ORD flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip all in one place. Select from our impressive range of stays and then add car rentals, activities and flights 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 Regional Airport (ROA) to O'Hare Intl. Airport (ORD)?
In most instances, you're able to reschedule or cancel your ROA to ORD flight. However, there may be additional fees, especially if you booked more than 24 hours ago. Check your itinerary for the airline's guidelines and fees on flight changes, or if you'd like more information, visit our Customer Service portal.

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*Available to One Key members.