Cheap flights from Virginia to Chicago

Travel > North America > United States > Virginia to Chicago flights

Though residents complain about the cold weather that lasts almost through the whole year, at least on a winter day, they can duck into such popular clubs as Andy's, where there's hot jazz even at noon. The best time to visit is between May and October when the weather is the most predictable. Then you could head out to ivy-covered Wrigley Field to catch baseball's Cubs in action, or take a cruise boat under the bridges of the Chicago River at sunset.... (read more in our Chicago Travel Guide)

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Check our newest flight offers to Chicago:

  • $187Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Richmond, VA (RIC)Chicago, IL (ORD)11/12/202012:00 pm
    Chicago, IL (ORD)Richmond, VA (RIC)11/20/202002:15 pm
    cheapoair.com check price
  • $209Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Richmond, VA (RIC)Chicago, IL (ORD)11/12/202007:25 pm
    Chicago, IL (ORD)Richmond, VA (RIC)11/20/202011:31 am
    cheapoair.com check price
  • $223Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Richmond, VA (RIC)Chicago, IL (ORD)11/01/202012:00 pm
    Chicago, IL (ORD)Richmond, VA (RIC)11/15/202002:29 pm
    cheapoair.com check price
  • $325Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Richmond, VA (RIC)Chicago, IL (ORD)12/11/202012:15 pm
    Chicago, IL (ORD)Richmond, VA (RIC)12/26/202006:30 pm
    cheapoair.com check price
  • $6627Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Norfolk, VA (ORF)Chicago, IL (ORD)12/03/202008:37 am
    Chicago, IL (ORD)Norfolk, VA (ORF)12/10/202003:20 pm
    cheapoair.com check price
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$1088 Depart: 12/30/2020
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$878 Depart: 12/16/2020
Return: 12/22/2020

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$878 Depart: 12/01/2020
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$676 Depart: 10/30/2020
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Alaska AirlinesHonolulu To Washington DC Alaska Airlines airfares from Honolulu in October
$970 Depart: 10/26/2020
Return: 11/01/2020

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Multiple AirlinesHonolulu To Boston Multiple Airlines airfares from Honolulu in November
$681 Depart: 11/04/2020
Return: 11/18/2020

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