Title: Roanoke to Chicago cheap flights from $136 (ROA to MDW) - 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 (MDW) [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 Midway Airport (MDW) - ![](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:MDW,departure:3/25/2026TANYT&leg2=from:MDW,to:ROA,departure:4/1/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## Cheap Flights from Roanoke to Chicago (ROA-MDW) Prices were available within the past 7 days and start at $136 for one-way flights and $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![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 1 day 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) Sun, Sep 6 - Tue, Sep 22 ROA Roanoke MDW Chicago $269 Roundtrip found 6 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:MDW,departure:9/6/2026TANYT&leg2=from:MDW,to:ROA,departure:9/22/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:268.40&airProductToken=AQpvCjUIxJgBEgQyODE4GNEDIOBcKLiHlwMwj4iXAzhFQABYAWoJTUFJTkJBU0lDcghYRlZOQTBCUQo2CMSYARIEMTA2MxjgXCDssAEo54iXAzDaiZcDOEVAAVgBaglNQUlOQkFTSUNyCFhGVk5BMEJRCm8KNgjEmAESBDE3MjgY7LABIOBcKKHBmAMwocKYAzhFQABYAWoJTUFJTkJBU0lDcghYRlZOQTBCUQo1CMSYARIEMjM3MhjgXCDRAyiRw5gDMObDmAM4RUABWAFqCU1BSU5CQVNJQ3IIWEZWTkEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Apr 25 - Mon, May 4 ROA Roanoke MDW Chicago $280 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:MDW,departure:4/25/2026TANYT&leg2=from:MDW,to:ROA,departure:5/4/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:279.41&airProductToken=AQpvCjUIxJgBEgQyODE4GNEDIOBcKPijiwMw16SLAzhFQABYAWoJTUFJTkJBU0lDcghYQVZTSDNCUQo2CMSYARIEMTA2MxjgXCDssAEoq6WLAzCgposDOEVAAVgBaglNQUlOQkFTSUNyCFhBVlNIM0JRCm8KNgjEmAESBDE3MjgY7LABIOBcKP2OjAMw-I-MAzhFQABYAWoJTUFJTkJBU0lDcghYRlVOQTBCUQo1CMSYARIEMjM3MhjgXCDRAyiUkYwDMOmRjAM4RUABWAFqCU1BSU5CQVNJQ3IIWEZVTkEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Apr 22 - Sat, Apr 25 ROA Roanoke MDW Chicago $288 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:MDW,departure:4/22/2026TANYT&leg2=from:MDW,to:ROA,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:287.41&airProductToken=AQpvCjUIxJgBEgQyODE4GNEDIOBcKJiCiwMw94KLAzhFQABYAWoJTUFJTkJBU0lDcghYRlZOQTBCUQo2CMSYARIEMTA2MxjgXCDssAEoy4OLAzDAhIsDOEVAAVgBaglNQUlOQkFTSUNyCFhGVk5BMEJRCm8KNgjEmAESBDE3MjgY7LABIOBcKN2piwMw2KqLAzhFQABYAWoJTUFJTkJBU0lDcghUQVZOQTBCUQo1CMSYARIEMjM3MhjgXCDRAyj0q4sDMMmsiwM4RUABWAFqCU1BSU5CQVNJQ3IIVEFWTkEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Sep 6 - Tue, Sep 22 ROA Roanoke MDW Chicago $304 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:MDW,departure:9/6/2026TANYT&leg2=from:MDW,to:ROA,departure:9/22/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:303.40&airProductToken=AQpvCjUIxJgBEgQyODE4GNEDIOBcKLiHlwMwj4iXAzhFQABYAWoJTUFJTkJBU0lDcghURjdOQTBCUQo2CMSYARIEMTA2MxjgXCDssAEo54iXAzDaiZcDOEVAAVgBaglNQUlOQkFTSUNyCFRGN05BMEJRCm8KNgjEmAESBDE3MjgY7LABIOBcKKHBmAMwocKYAzhFQABYAWoJTUFJTkJBU0lDcghWRlZOQTBCUQo1CMSYARIEMjM3MhjgXCDRAyiRw5gDMObDmAM4RUABWAFqCU1BSU5CQVNJQ3IIVkZWTkEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Sep 6 - Tue, Sep 22 ROA Roanoke MDW Chicago $308 Roundtrip found 6 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:MDW,departure:9/6/2026TANYT&leg2=from:MDW,to:ROA,departure:9/22/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:307.40&airProductToken=AQpvCjUIxJgBEgQyODE4GNEDIOBcKLiHlwMwj4iXAzhFQABYAWoJTUFJTkJBU0lDcghYRlZOQTBCUQo2CMSYARIEMTA2MxjgXCDssAEo54iXAzDaiZcDOEVAAVgBaglNQUlOQkFTSUNyCFhGVk5BMEJRCm8KNgjEmAESBDI0MTcY7LABIOBcKJ2_mAMwlsCYAzhFQABYAWoJTUFJTkJBU0lDcghUQVZOQTBCUQo1CMSYARIEMzgwORjgXCDRAyj5wJgDMNTBmAM4RUABWAFqCU1BSU5CQVNJQ3IIVEFWTkEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![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 $310 Roundtrip found 1 day 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:309.40&airProductToken=AQpvCjUIxJgBEgQyODE4GNEDIOBcKJi9jQMw872NAzhFQABYAWoJTUFJTkJBU0lDcghYRlZOQTBCUQo2CMSYARIEMTA2MxjgXCDssAEo0b6NAzDEv40DOEVAAVgBaglNQUlOQkFTSUNyCFhGVk5BMEJRCm8KNgjEmAESBDI0MTcY7LABIOBcKM-PjgMwyJCOAzhFQABYAWoJTUFJTkJBU0lDcghVRldOQTBCUQo1CMSYARIENTAyORjgXCDRAyickY4DMPqRjgM4RUABWAFqCU1BSU5CQVNJQ3IIVUZXTkEwQlESDAgBEAEYASoCREwyABgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Mar 24 - Tue, Mar 31 ROA Roanoke MDW Chicago $314 Roundtrip found 23 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:MDW,departure:3/24/2026TANYT&leg2=from:MDW,to:ROA,departure:3/31/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:313.40&airProductToken=AQpvCjUIxJgBEgQyODE4GNEDIOBcKPi7iAMw2LyIAzhFQABYAWoJTUFJTkJBU0lDcghURlVPQTBCUQo2CMSYARIEMTA2MxjgXCDssAEoq72IAzCgvogDOEVAAVgBaglNQUlOQkFTSUNyCFRGVU9BMEJRCm8KNgjEmAESBDIwNjAY7LABIOBcKOuQiQMw6JGJAzhFQABYAWoJTUFJTkJBU0lDcghYRlZOQTBCUQo1CMSYARIEMjM3MhjgXCDRAyjAkokDMJSTiQM4RUABWAFqCU1BSU5CQVNJQ3IIWEZWTkEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![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 $319 Roundtrip found 1 day 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:318.40&airProductToken=AQpvCjUIxJgBEgQyODE4GNEDIOBcKJi9jQMw872NAzhYQABYAWoJTUFJTkNMQVNDcghYRlZOQTBNTAo2CMSYARIEMTA2MxjgXCDssAEo0b6NAzDEv40DOFhAAVgBaglNQUlOQ0xBU0NyCFhGVk5BME1MCm8KNgjEmAESBDE3MjgY7LABIOBcKNSRjgMw0pKOAzhYQABYAWoJTUFJTkNMQVNDcghYRlZOQTBNTAo1CMSYARIEMjM3MhjgXCDRAyj5k44DMNKUjgM4WEABWAFqCU1BSU5DTEFTQ3IIWEZWTkEwTUwSDAgBEAEYASoCREwyABgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Aug 21 - Tue, Aug 25 ROA Roanoke MDW Chicago $324 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ROA,to:MDW,departure:8/21/2026TANYT&leg2=from:MDW,to:ROA,departure:8/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:323.41&airProductToken=AQpvCjUIxJgBEgQyODE4GNEDIOBcKLjTlQMwj9SVAzhFQABYAWoJTUFJTkJBU0lDcghYRlVOQTBCUQo2CMSYARIEMTA2MxjgXCDssAEo59SVAzDa1ZUDOEVAAVgBaglNQUlOQkFTSUNyCFhGVU5BMEJRCm8KNgjEmAESBDI0MTcY7LABIOBcKJ2ElgMwloWWAzhFQABYAWoJTUFJTkJBU0lDcghURldPSDNCUQo1CMSYARIEMzgwORjgXCDRAyj5hZYDMNSGlgM4RUABWAFqCU1BSU5CQVNJQ3IIVEZXT0gzQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![](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:3/25/2026TANYT&leg2=from:ORD,to:ROA,departure:4/1/2026TANYT&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 $269 ](https://www.expedia.com/Flights-Search?leg1=from:ROA,to:ORD,departure:3/25/2026TANYT&leg2=from:ORD,to:ROA,departure:4/1/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Frequently asked questions ### How much does a flight from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.) cost? ### What is the cheapest month to fly from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)? ### Which airlines fly direct from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)? ### What is the cheapest airline that flies from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)? ### How do I find cheap flights from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)? ### What is the best time to fly from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)? ### What is the earliest flight from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)? ### What are the most popular departure times for flights from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)? ### How long does it take to fly from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)? ### Can you fly business or first class from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)? ### How do I earn miles on a Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.) flight with Expedia? ### What airports do you fly into for Chicago from Roanoke Regional (ROA)? ### Is it cheaper to buy a plane ticket from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.) at the last minute? ### Is it cheaper to book a Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.) flight and hotel package? ### Can I cancel or change the date of my flight from Roanoke, VA (ROA-Roanoke Regional) to Chicago, IL (MDW-Midway Intl.)? ## Travel information | Origin airport | Roanoke Regional | | ------------------- | ---------------- | | Destination airport | Midway Intl. | | Airlines serving | Delta | | Roundtrip price | $248 | | Distance | 515 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 May. 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 - Other - [Chicago Hotels ](https://www.expedia.com/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Hotels near Downtown Chicago ](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Hotels near Midway Station ](https://www.expedia.com/Midway-Station-Hotels.d6211025.Travel-Guide-Hotels) - [Hotels near Garfield Ridge ](https://www.expedia.com/Garfield-Ridge-Chicago-Hotels.0-n6132357-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Garfield Ridge ](https://www.expedia.com/Garfield-Ridge-Chicago-Hotels-Cheap-Hotels.0-n6132357-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels near Pulaski Station ](https://www.expedia.com/Pulaski-Station-Hotels.d6211019.Travel-Guide-Hotels) - [Hotels near West Lawn ](https://www.expedia.com/West-Lawn-Chicago-Hotels.0-n6132413-0.Travel-Guide-Filter-Hotels) - 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