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Cheap Flights from Roanoke to Chicago

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      Compare Roanoke to Chicago flight deals

      Find the cheapest month or even day of the year to fly to Chicago

      Book the best Chicago fare with no extra fees

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      Flight deals from Roanoke to Chicago

      Looking for a cheap last-minute deal or the best round-trip flight from Roanoke Airport to Chicago? If you want to travel next month, round-trip fares start from ฿11,658. Find the lowest prices on one-way and round-trip tickets right here.
      Chicago.฿11,331 per passenger.Departing Thu, Mar 25, returning Thu, Apr 1.Round-trip flight with United.Outbound direct flight with United departing from Roanoke on Thu, Mar 25, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Thu, Apr 1, arriving in Roanoke.Price includes taxes and charges.From ฿11,331, select.
      Chicago.฿11,331 per passenger.Departing Sat, Jan 23, returning Sat, Jan 30.Round-trip flight with United.Outbound direct flight with United departing from Roanoke on Sat, Jan 23, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Sat, Jan 30, arriving in Roanoke.Price includes taxes and charges.From ฿11,331, select.
      Chicago.฿11,684 per passenger.Departing Fri, Dec 25, returning Wed, Dec 30.Round-trip flight with United.Outbound direct flight with United departing from Roanoke on Fri, Dec 25, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Wed, Dec 30, arriving in Roanoke.Price includes taxes and charges.From ฿11,684, select.
      Chicago.฿11,784 per passenger.Departing Sat, Mar 20, returning Sat, Mar 27.Round-trip flight with United.Outbound direct flight with United departing from Roanoke on Sat, Mar 20, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Sat, Mar 27, arriving in Roanoke.Price includes taxes and charges.From ฿11,784, select.
      Chicago.฿11,784 per passenger.Departing Sat, Apr 3, returning Sat, Apr 10.Round-trip flight with United.Outbound direct flight with United departing from Roanoke on Sat, Apr 3, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Sat, Apr 10, arriving in Roanoke.Price includes taxes and charges.From ฿11,784, select.
      Chicago.฿12,132 per passenger.Departing Fri, Dec 25, returning Fri, Jan 1.Round-trip flight with United.Outbound direct flight with United departing from Roanoke on Fri, Dec 25, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Fri, Jan 1, arriving in Roanoke.Price includes taxes and charges.From ฿12,132, select.
      Chicago.฿12,132 per passenger.Departing Wed, Feb 10, returning Wed, Feb 17.Round-trip flight with United.Outbound direct flight with United departing from Roanoke on Wed, Feb 10, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Wed, Feb 17, arriving in Roanoke.Price includes taxes and charges.From ฿12,132, select.
      Chicago.฿12,153 per passenger.Departing Mon, Feb 22, returning Mon, Mar 1.Round-trip flight with United.Outbound direct flight with United departing from Roanoke on Mon, Feb 22, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Mon, Mar 1, arriving in Roanoke.Price includes taxes and charges.From ฿12,153, select.
      Chicago.฿12,830 per passenger.Departing Fri, May 28, returning Sun, Jun 6.Round-trip flight with United.Outbound direct flight with United departing from Roanoke on Fri, May 28, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Sun, Jun 6, arriving in Roanoke.Price includes taxes and charges.From ฿12,830, select.
      Chicago.฿13,136 per passenger.Departing Fri, Nov 27, returning Tue, Dec 1.Round-trip flight with United.Outbound direct flight with United departing from Roanoke on Fri, Nov 27, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Tue, Dec 1, arriving in Roanoke.Price includes taxes and charges.From ฿13,136, select.
      Chicago.฿13,981 per passenger.Departing Tue, Nov 24, returning Sat, Nov 28.Round-trip flight with United.Outbound direct flight with United departing from Roanoke on Tue, Nov 24, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Sat, Nov 28, arriving in Roanoke.Price includes taxes and charges.From ฿13,981, select.
      How did we find these deals? The deals you see here are the lowest prices for flight tickets from Roanoke to Chicago found in the last 4 days, and are subject to change and availability.

      Find the cheapest month to fly from Roanoke to Chicago

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Roanoke to Chicago flights are currently cheapest in January.
      Nov
      from ฿13,950
      Dec
      from ฿11,658
      Jan
      from ฿11,306
      Feb
      from ฿12,106
      Mar
      from ฿11,759
      Apr
      from ฿11,759
      May
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      Jun
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      Jul
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      Aug
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      Sep
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      Oct
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      Direct flights from Roanoke to Chicago

      Air New Zealand
      American Airlines
      ANA (All Nippon Airways)
      Emirates
      Envoy Air
      GoJet Airlines
      Lufthansa
      PSA Airlines
      Qatar Airways
      Republic Airways
      SkyWest Airlines
      United

      Alternative Roanoke to Chicago routes

      Looking for the cheapest, fastest or easiest route from Roanoke to Chicago? You could fly into the following airports instead.

      Chicago Midway

      14km from central Chicago
      Closest
      from ฿13,188
      Search flights

      Chicago O'Hare International

      25km from central Chicago
      Cheapest
      from ฿11,331
      Search flights

      Chicago Rockford

      127km from central Chicago
      Search flights

      Roanoke to Chicago: Flight information

      The things to know before you go.
      Cheapest flight found฿11,306
      Cheapest month to flyJanuary
      Average flight time2 hrs, 13 mins
      Most popular airlineUnited
      Average flights per week262

      Finding cheap flights from Roanoke to Chicago: Frequently asked questions

      There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.
      The best price we found for a round-trip flight from Roanoke to Chicago is ฿11,306. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      2 hours and 13 minutes is the average flight time from Roanoke to Chicago.
      United, SkyWest Airlines and American Airlines fly direct from Roanoke to Chicago.
      There are 131 flights per week flying from Roanoke to Chicago, as of November 2026.
      The cheapest month to fly from Roanoke to Chicago is usually January.
      If you're flying from Roanoke Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the center of Chicago. We've found flights to this airport from ฿11,306.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Roanoke Airport to Chicago on Saturday, January 23, 2027.
      Yes – the average flight time is 2 hours and 13 minutes.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

      In November, the average temperature is usually around 7°C. July is typically the warmest month in Chicago, when it usually averages around 27°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -5°C. The rainiest month is June.
      Currently, United offers the cheapest flight tickets to Chicago.

      How to find cheap flights to Chicago from Roanoke

      Looking for cheap tickets from Roanoke to Chicago? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

      • Simply hit "search." From Delta Air Lines to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Roanoke to Chicago. And with us, there are no hidden fees – what you see is what you pay.
      • Compare flight deals to Chicago from Roanoke from over 1,000 providers. Then choose the cheapest plane tickets or fastest journeys.
      • Flex your dates to find the best Roanoke–Chicago ticket prices. If you're flexible when it comes to your travel dates, use Skyscanner's "Whole month" tool to find the cheapest month, and even day to fly to Chicago from Roanoke.
      • Set up a Price Alert. You can easily track the fare of your cheap Roanoke–Chicago flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
      • Fly without stops. Only interested in direct flights between Roanoke and Chicago? Make sure to tick "Direct flights only" when performing a search. If there are direct flights available on the route, these will appear in the results.
      • Find the cheapest Business Class flights from Roanoke and Chicago. We scour the Internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just stumble on a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
      • Include nearby airports in your search. Widen your search for Roanoke to Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save the next time you travel.

        • Combine your flight to Chicago from Roanoke with hotels and car rental

        Once you've secured your cheap flight ticket from Roanoke to Chicago, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car rental companies at once so you get the best car rental price for your trip.


      Plan the rest of your trip from Roanoke to Chicago

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.