Title: Roanoke to Chicago cheap flights from $136 (ROA to CHI) - Expedia.com ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $136 Cheap Flights from Roanoke (ROA) to Chicago (CHI) [View $136 flight on Wed, Apr 22, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:ROA,to:MDW,departure:4/22/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:135.20&airProductToken=AQpvCjUIxJgBEgQyODE4GNEDIOBcKJiCiwMw94KLAzhFQABYAWoJTUFJTkJBU0lDcghYQVZTSDNCUQo2CMSYARIEMTA2MxjgXCDssAEoy4OLAzDAhIsDOEVAAVgBaglNQUlOQkFTSUNyCFhBVlNIM0JREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ## Popular airlines from Roanoke Regional Airport (ROA) to Chicago - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:CHI,departure:3/29/2026TANYT&leg2=from:CHI,to:ROA,departure:4/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:CHI,departure:3/29/2026TANYT&leg2=from:CHI,to:ROA,departure:4/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:CHI,departure:3/29/2026TANYT&leg2=from:CHI,to:ROA,departure:4/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) ## Today's featured flight deals from Roanoke Regional Airport (ROA) to Chicago Nonstop Carry-on included Lower price than typical - Roanoke (ROA)Chicago (ORD) Thu, Mar 19 Sun, Mar 22 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip just found 20% less than typical $444 [](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:ORD,departure:3/19/2026TANYT&leg2=from:ORD,to:ROA,departure:3/22/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-5b0d8e3367e54463bc8202cdd5eb8ff2-163-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gBtaOpXaoBBwoDUk9BEACyAQcKA0NISRAA~AQozCjEIwYIBEgQ0NzIzGNEDIK4cKMaEiAMw0IWIAzhCQABYAWoFQkFTSUNyCFMwRldaTkJaCjMKMQjBggESBDQ2NzMYrhwg0QMo_ayIAzDvrYgDOEJAAFgBagVCQVNJQ3IITjdGSFpOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=701.00&displayPrice=443.80&src=dflp) - Roanoke (ROA)Chicago (ORD) Thu, Apr 16 Sun, Apr 19 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip just found 30% less than typical $249 [](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:ORD,departure:4/16/2026TANYT&leg2=from:ORD,to:ROA,departure:4/19/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-924a559da1f5448e8459e1b6d65a12c4-702-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gB_KipXaoBBwoDUk9BEACyAQcKA09SRBAA~AQozCjEIwYIBEgQ0NzIzGNEDIK4cKLC_igMwxsCKAzhCQABYAWoFQkFTSUNyCFFWRkhaTkJWCjMKMQjBggESBDQ2NzMYrhwg0QMog-iKAzD66IoDOEJAAFgBagVCQVNJQ3IIUVZGSFpOQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=459.00&displayPrice=248.80&src=dflp) - Roanoke (ROA)Chicago (ORD) Sun, Mar 29 Wed, Apr 8 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 10-day trip found 15 hours ago 25% less than typical $269 [](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:ORD,departure:3/29/2026TANYT&leg2=from:ORD,to:ROA,departure:4/8/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-aece642e1e5448fcb525fb100e27e635-650-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gB3IOmXaoBBwoDUk9BEACyAQcKA0NISRAA~AQozCjEIwYIBEgQ0NzIzGNEDIK4cKIb1iAMwkPaIAzhCQABYAWoFQkFTSUNyCFFVRkhaTkJYCjMKMQjBggESBDQ2NzMYrhwg0QMoo-yJAzCa7YkDOEJAAFgBagVCQVNJQ3IIUVZGSFpOQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=474.00&displayPrice=268.81&src=dflp) - Roanoke (ROA)Chicago (ORD) Mon, Mar 23 Wed, Apr 1 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 9-day trip found 16 hours ago 20% less than typical $324 [](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:ORD,departure:3/23/2026TANYT&leg2=from:ORD,to:ROA,departure:4/1/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-a6787d97d02540d0abcc537addfae504-48-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gBquKlXaoBBwoDUk9BEACyAQcKA09SRBAB~AQozCjEIwYIBEgQ0NzIzGNEDIK4cKMaxiAMw0LKIAzhCQABYAWoFQkFTSUNyCE43RkhaTkJYCjMKMQjBggESBDQ2NzMYrhwg0QMov52JAzCvnokDOEJAAFgBagVCQVNJQ3IIUVVGSFpOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=525.00&displayPrice=323.80&src=dflp) - Roanoke (ROA)Chicago (ORD) Thu, Apr 23 Sun, Apr 26 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip found 9 hours ago 25% less than typical $249 [](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:ORD,departure:4/23/2026TANYT&leg2=from:ORD,to:ROA,departure:4/26/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-faa3c03b6e67441b8b351979273487d3-1684-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gBtbWnXaoBBwoDUk9BEACyAQcKA0NISRAA~AQozCjEIwYIBEgQ0NzIzGNEDIK4cKJCOiwMwpo-LAzhCQABYAWoFQkFTSUNyCFFWRkhaTkJWCjMKMQjBggESBDQ2NzMYrhwg0QMo47aLAzDat4sDOEJAAFgBagVCQVNJQ3IIUVZGSFpOQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=444.00&displayPrice=248.80&src=dflp) - Roanoke (ROA)Chicago (ORD) Thu, Apr 2 Sun, Apr 5 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip found 2 hours ago 25% less than typical $269 [](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:ORD,departure:4/2/2026TANYT&leg2=from:ORD,to:ROA,departure:4/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-90505138d6944b96a49e1d145ba5e114-694-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gB2_moXaoBBwoDUk9BEACyAQcKA0NISRAC~AQozCjEIwYIBEgQ0NzIzGNEDIK4cKIaiiQMwkKOJAzhCQABYAWoFQkFTSUNyCFFVRkhaTkJYCjMKMQjBggESBDQ2NzMYrhwg0QMov8qJAzCvy4kDOEJAAFgBagVCQVNJQ3IIUVZGSFpOQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=461.00&displayPrice=268.81&src=dflp) - Roanoke (ROA)Chicago (ORD) Fri, Apr 3 Mon, Apr 6 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip found 2 hours ago 20% less than typical $269 [](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:ORD,departure:4/3/2026TANYT&leg2=from:ORD,to:ROA,departure:4/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-7a9e95ef5fde4cc6a9c51734eacf9d54-297-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gB2_qoXaoBBwoDUk9BEACyAQcKA0NISRAC~AQozCjEIwYIBEgQ0NzIzGNEDIK4cKKatiQMwsK6JAzhCQABYAWoFQkFTSUNyCFFVRkhaTkJYCjMKMQjBggESBDQ2NzMYrhwg0QMo39WJAzDP1okDOEJAAFgBagVCQVNJQ3IIUVZGSFpOQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=443.00&displayPrice=268.81&src=dflp) - Roanoke (ROA)Chicago (ORD) Fri, Apr 24 Mon, Apr 27 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip found 9 hours ago 25% less than typical $249 [](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:ORD,departure:4/24/2026TANYT&leg2=from:ORD,to:ROA,departure:4/27/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-c7421313777946b88cc9506613e3b384-1677-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gB3KOnXaoBBwoDUk9BEACyAQcKA09SRBAA~AQozCjEIwYIBEgQ0NzIzGNEDIK4cKLCZiwMwxpqLAzhCQABYAWoFQkFTSUNyCFFWRkhaTkJWCjMKMQjBggESBDQ2NzMYrhwg0QMog8KLAzD6wosDOEJAAFgBagVCQVNJQ3IIUVZGSFpOQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=418.00&displayPrice=248.80&src=dflp) - Roanoke (ROA)Chicago (ORD) Thu, Apr 2 Mon, Apr 6 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 4-day trip found 2 hours ago 20% less than typical $269 [](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:ORD,departure:4/2/2026TANYT&leg2=from:ORD,to:ROA,departure:4/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-6f35e286326746c4b26f50abc394a1b9-77-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gBm_qoXaoBBwoDUk9BEACyAQcKA0NISRAC~AQozCjEIwYIBEgQ0NzIzGNEDIK4cKIaiiQMwkKOJAzhCQABYAWoFQkFTSUNyCFFVRkhaTkJYCjMKMQjBggESBDQ2NzMYrhwg0QMo39WJAzDP1okDOEJAAFgBagVCQVNJQ3IIUVZGSFpOQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=429.00&displayPrice=268.81&src=dflp) ## Cheap Flights from Roanoke to Chicago (ROA-CHI) Prices were available within the past 7 days and start at $136 for one-way flights and $241 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Apr 14 - Sat, Apr 18 ROA Roanoke ORD Chicago $241 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:ORD,departure:4/14/2026TANYT&leg2=from:ORD,to:ROA,departure:4/18/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:240.63&airProductToken=AQo4CjYI1YIBEgQ0NTE0GNEDIK4cKLiqigMwuauKAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4KOAo2CNWCARIENDYwORiuHCDRAyj73IoDMPXdigM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, May 23 - Tue, May 26 ROA Roanoke RFD Rockford $247 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:RFD,departure:5/23/2026TANYT&leg2=from:RFD,to:ROA,departure:5/26/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:246.94&airProductToken=AQpmCjEIwYIBEgQ0NzIzGNEDIK4cKPjejQMw_t-NAzhCQABYAWoFQkFTSUNyCFFWRkhaTkJWCjEIwYIBEgQ2NTc0GK4cILEZKMrgjQMwqeGNAzhCQAFYAWoFQkFTSUNyCFFWRkhaTkJWCmYKMQjBggESBDY1NzYYsRkgrhwov4WOAzCeho4DOEJAAFgBagVCQVNJQ3IIUVZGSFpOQlYKMQjBggESBDQ2NzMYrhwg0QMo04eOAzDPiI4DOEJAAVgBagVCQVNJQ3IIUVZGSFpOQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, May 20 - Wed, May 27 ROA Roanoke MDW Chicago $249 Roundtrip found 5 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:MDW,departure:5/20/2026TANYT&leg2=from:MDW,to:ROA,departure:5/27/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:248.40&airProductToken=AQpvCjUIxJgBEgQyODE4GNEDIOBcKJi9jQMw872NAzhFQABYAWoJTUFJTkJBU0lDcghYRlZOQTBCUQo2CMSYARIEMTA2MxjgXCDssAEo0b6NAzDEv40DOEVAAVgBaglNQUlOQkFTSUNyCFhGVk5BMEJRCm8KNgjEmAESBDE3MjgY7LABIOBcKNSRjgMw0pKOAzhFQABYAWoJTUFJTkJBU0lDcghYRlZOQTBCUQo1CMSYARIEMjM3MhjgXCDRAyj5k44DMNKUjgM4RUABWAFqCU1BSU5CQVNJQ3IIWEZWTkEwQlESDAgBEAEYASoCREwyABgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Jun 8 - Tue, Jun 16 ROA Roanoke ORD Chicago $249 Roundtrip found 5 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:ORD,departure:6/8/2026TANYT&leg2=from:ORD,to:ROA,departure:6/16/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:248.40&airProductToken=AQpECiAIxJgBEgQzODA5GNEDIOBcKLaZjwMwmZqPAzhFQABYAQogCMSYARIEMTE5ORjgXCCuHCjlmo8DMOebjwM4RUABWAEKRAogCMSYARIEMjczOBiuHCDgXCj_8o8DMP3zjwM4RUAAWAEKIAjEmAESBDIzNzIY4Fwg0QMo0fSPAzCl9Y8DOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Apr 16 - Sun, Apr 19 ROA Roanoke ORD Chicago $249 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:ORD,departure:4/16/2026TANYT&leg2=from:ORD,to:ROA,departure:4/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:248.80&airProductToken=AQozCjEIwYIBEgQ0NzIzGNEDIK4cKLC_igMwxsCKAzhCQABYAWoFQkFTSUNyCFFWRkhaTkJWCjMKMQjBggESBDQ2NzMYrhwg0QMog-iKAzD66IoDOEJAAFgBagVCQVNJQ3IIUVZGSFpOQlYSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, May 5 - Wed, May 6 ROA Roanoke ORD Chicago $251 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:ORD,departure:5/5/2026TANYT&leg2=from:ORD,to:ROA,departure:5/6/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:250.80&airProductToken=AQozCjEIwYIBEgQ0NzIzGNEDIK4cKJCVjAMwppaMAzhCQABYAWoFQkFTSUNyCE9WQVdVU0JWEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Apr 16 - Sun, Apr 19 ROA Roanoke ORD Chicago $259 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:ORD,departure:4/16/2026TANYT&leg2=from:ORD,to:ROA,departure:4/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:258.60&airProductToken=AQpnCjIIwYIBEgQ1ODQ1GNEDIOKaASigxYoDMPLFigM4QkAAWAFqBUJBU0lDcghRVkZIWk5CVgoxCMGCARIDNjg5GOKaASCuHCjBxooDMMbHigM4QkABWAFqBUJBU0lDcghRVkZIWk5CVgozCjEIwYIBEgQ0NjczGK4cINEDKIPoigMw-uiKAzhCQABYAWoFQkFTSUNyCFFWRkhaTkJWEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Apr 10 - Sat, Apr 11 ROA Roanoke ORD Chicago $260 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:ORD,departure:4/10/2026TANYT&leg2=from:ORD,to:ROA,departure:4/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:259.61&airProductToken=AQozCjEIwYIBEgQ0NzIzGNEDIK4cKPD7iQMwhv2JAzhCQABYAWoFQkFTSUNyCE9WRkhaTkJWCmgKMgjBggESBDIxNDkYrhwg4poBKJOIigMwlomKAzhCQABYAWoFQkFTSUNyCE5XRldVTkJWCjIIwYIBEgQ1ODgxGOKaASDRAyjliYoDMLWKigM4QkABWAFqBUJBU0lDcghOV0ZXVU5CVhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, Jun 3 - Sun, Jun 7 ROA Roanoke ORD Chicago $262 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:ORD,departure:6/3/2026TANYT&leg2=from:ORD,to:ROA,departure:6/7/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:261.70&airProductToken=AQo4CjYI1YIBEgQ0NTg1GNEDIK4cKPrcjgMw_N2OAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4KOAo2CNWCARIENDE4NhiuHCDRAyjBiI8DMLqJjwM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, Jun 24 - Tue, Jun 30 ROA Roanoke ORD Chicago $266 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:ORD,departure:6/24/2026TANYT&leg2=from:ORD,to:ROA,departure:6/30/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:266.00&airProductToken=AQo4CjYI1YIBEgQ1NTAwGNEDIK4cKKDHkAMwpciQAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4KOAo2CNWCARIENTMzNxiuHCDRAyjSjpEDMNCPkQM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=FTG_SPRING_PROMO_) ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:ORD,departure:3/29/2026TANYT&leg2=from:ORD,to:ROA,departure:3/30/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. Cheapest 23 min [Flights from $407 ](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:ORD,departure:3/29/2026TANYT&leg2=from:ORD,to:ROA,departure:3/30/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) [](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:MDW,departure:3/29/2026TANYT&leg2=from:MDW,to:ROA,departure:4/8/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) MDW Midway Intl. Closest 16 min [Flights from $799 ](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:MDW,departure:3/29/2026TANYT&leg2=from:MDW,to:ROA,departure:4/8/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Find the cheapest month to fly from Roanoke (ROA) to Chicago (CHI) ### November is typically the cheapest month to fly From $207 - $468 per traveler. ## Travel information | Origin airport | Roanoke Regional | | ------------------- | ---------------- | | Destination airport | O'Hare Intl. | | Roundtrip price | $241 | | Distance | 529 mi | ## 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 April. 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 $136 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](https://www.expedia.com/package-deals). 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. \*Flight schedules are subject to change. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Garden Prairie Hotels ](https://www.expedia.com/Garden-Prairie-Hotels.d3000346277.Travel-Guide-Hotels) - [5 Star Hotels in Garden Prairie ](https://www.expedia.com/5Star-Garden-Prairie-Hotels.s50-0-d3000346277.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Garden Prairie ](https://www.expedia.com/3Star-Garden-Prairie-Hotels.s30-0-d3000346277.Travel-Guide-Filter-Hotels) - [Kirkland Hotels ](https://www.expedia.com/Kirkland-Hotels.d553248634983555364.Travel-Guide-Hotels) - [Belvidere Hotels ](https://www.expedia.com/Belvidere-Hotels.d55583.Travel-Guide-Hotels) - [Marengo Hotels ](https://www.expedia.com/Marengo-Hotels.d553248634983534917.Travel-Guide-Hotels) - [Cheap Hotels in Belvidere ](https://www.expedia.com/Belvidere-Hotels-Cheap-Hotels.0-0-d55583-tCheapHotels.Travel-Guide-Filter-Hotels) - [Motels in Belvidere ](https://www.expedia.com/Belvidere-Motels.d55583-aaMotels.Travel-Guide-Accommodation) - 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