Cheap flights from Connecticut to Chicago

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

Founded in the early 1800s, Chicago is positioned between civilization and wilderness and many aspects of modern life had their start here. Chicago really does have it all, with less infrastructural problems than its coastal rivals.... (read more in our Chicago Travel Guide)

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Cheapest flights found for the next 6 months

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Hartford 

Check our newest flight offers to Chicago:

  • $141Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Windsor Locks, CT (BDL)Chicago, IL (ORD)03/22/202111:50 am
    Chicago, IL (ORD)Windsor Locks, CT (BDL)03/30/202103:55 pm
    cheapoair.com check price
  • $248Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Windsor Locks, CT (BDL)Chicago, IL (ORD)03/27/202103:30 pm
    Chicago, IL (ORD)Windsor Locks, CT (BDL)04/04/202105:17 am
    cheapoair.com check price
  • $287Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Windsor Locks, CT (BDL)Chicago, IL (ORD)03/22/202111:32 am
    Chicago, IL (ORD)Windsor Locks, CT (BDL)03/30/202103:55 pm
    cheapoair.com check price
  • $4180Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Windsor Locks, CT (BDL)Chicago, IL (ORD)03/27/202103:30 pm
    Chicago, IL (ORD)Windsor Locks, CT (BDL)04/04/202105:09 pm
    cheapoair.com check price
  • $10089Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Windsor Locks, CT (BDL)Chicago, IL (MDW)03/27/202107:29 am
    Chicago, IL (MDW)Windsor Locks, CT (BDL)04/04/202105:17 am
    cheapoair.com check price
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