$199 Cheap Flights from Roanoke (ROA) to Chicago (ORD)

Roanoke (ROA) to Chicago (ORD) at a glance

Travel from Roanoke (ROA) to Chicago (ORD) with a range of airlines offering convenient options for this domestic short-haul journey. Discover affordable flights from Roanoke as you compare itineraries that suit your budget and schedule, allowing you to fully enjoy the iconic attractions and neighborhoods of Chicago. Check out key details for flights departing from Roanoke Regional Airport (ROA) to O'Hare International Airport (ORD).

• Fastest flight duration: around 2h 15m non-stop
• Route distance: roughly 500 miles (800 km)
• Flights per week: around 13 departures on average
• Typical fares (one-way): economy tickets often range from $105–$430, depending on seasonality and how far ahead you book

Flights from Roanoke Regional Airport (ROA) to O'Hare International Airport (ORD)

Based on recent travel patterns, here are the top airlines preferred by travelers flying from Roanoke to Chicago, featuring both non-stop and one-stop flight options. Common layovers include Charlotte-Douglas International Airport (CLT) with an approximate 1 hour and 15-minute stop, Washington Dulles International Airport (IAD) also around 1 hour and 15 minutes, and Philadelphia International Airport (PHL) with about a 1 hour and 45-minute layover. This flexibility allows you to compare prices, total travel times, and cabin classes for the best itinerary.

• United: This comprehensive airline provides both non-stop and one-stop options, with one-way ticket prices generally between $105 and $465. United operates around 73% of flights on this route, featuring a standard non-stop travel duration of 2 hours and 15 minutes.
• American Airlines: As a full-service airline, American Airlines offers non-stop and one-stop flights, with one-way fares typically ranging from $105 to $390. They represent about 25% of departures on this route, maintaining a usual non-stop flying time of 2 hours and 15 minutes.
• Delta: Delta operates one-stop services, with one-way prices usually falling between $130 and $675. This carrier accounts for roughly 2% of departures on this route, with an in-flight duration of 3 hours and 45 minutes, leading to an overall travel time of about 5 hours, including layover.

Travelers flying from Roanoke to Chicago can enhance their experience by upgrading to first class, available through United and American Airlines on this route.

Best time to fly from Roanoke (ROA) to Chicago (ORD)

The most popular months for travelers flying from Roanoke to Chicago are January, March, and April, when peak temperatures in Chicago reach up to 46°F in April. If you prefer quieter travel, consider June, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 67.3°F. For better deals, February usually offers the lowest average one-way fare around $181. Flight availability peaks in November, with approximately 17 flights per week, making it easier to find convenient departure times. January has the fewest flights, with approximately 10 flights per week.

• Cheapest time to fly: February usually offers good deals with average one-way fare around $181, roughly 14% cheaper than the yearly average.
• More budget-friendly months to fly: November, September, and December typically offer average one-way fares of around $192.
• Most flight options: November has the highest number of flights from Roanoke to Chicago, with approximately 17 flights per week, giving you more flexibility in scheduling your trip.

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative route from Roanoke (ROA) to Chicago (ORD)

• Lynchburg to Chicago (LYH-ORD): Lynchburg Regional Airport (LYH) is located roughly 43 miles from Roanoke Regional Airport (ROA). One-way economy fares for this route generally fall between $150 and $385, influenced by the season and how early tickets are booked. Travelers can choose from both non-stop and one-stop flights, with most connections occurring at Charlotte-Douglas International Airport (CLT). Major airlines operating on this route include American Airlines and United.

How to find the best prices for flights from Roanoke (ROA) to Chicago (ORD)

Getting some of the best deals on flights from Roanoke to Chicago is all about timing and flexibility. Here are some key tips to help you save:

1. Best times to book and fly: cheaper fares are usually found when booking 2 to 8 weeks in advance, which coincides with when most travelers make their reservations. Morning departures between 5 a.m. and 12 p.m. tend to be less expensive and are also the most popular flight times. Additionally, flying on Fridays offers both lower prices and is the busiest travel day.
2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at O'Hare International Airport from Roanoke Regional Airport

Chicago welcomes travelers from Roanoke with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:

• Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
• Car rental: Renting a car from O'Hare International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at O'Hare International Airport on Expedia.
• Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
• Public transportation: From O'Hare International Airport, O'Hare Station, a metro station, is located about 0.1 miles away on foot, while Rosemont Station, a train station, is about 2.2 miles away by car, providing convenient access to public transport options.

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 November. 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 $199 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.