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:

  • $279Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Windsor Locks, CT (BDL)Chicago, IL (ORD)07/22/202207:00 am
    Chicago, IL (ORD)Windsor Locks, CT (BDL)07/31/202205:35 pm
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  • $299Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Windsor Locks, CT (BDL)Chicago, IL (ORD)07/12/202207:00 am
    Chicago, IL (ORD)Windsor Locks, CT (BDL)07/17/202205:35 pm
    cheapoair.com check price
  • $299Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Windsor Locks, CT (BDL)Chicago, IL (ORD)07/09/202207:00 am
    Chicago, IL (ORD)Windsor Locks, CT (BDL)07/14/202205:35 pm
    cheapoair.com check price
  • $499Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Windsor Locks, CT (BDL)Chicago, IL (MDW)07/09/202209:59 pm
    Chicago, IL (MDW)Windsor Locks, CT (BDL)07/14/202211:05 am
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  • $598Sun Country Airlines flight Sun Country Airlines 
    FromToDepartureTime
    Windsor Locks, CT (BDL)Chicago, IL (ORD)07/22/202212:00 pm
    Chicago, IL (ORD)Windsor Locks, CT (BDL)07/31/202207:00 pm
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Jetblue AirwaysNew Orleans To Buffalo Jetblue Airways airfares from New Orleans in December
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Qatar AirwaysDallas To Tokyo Qatar Airways airfares from Dallas in July
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Return: 07/17/2022

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Multiple AirlinesIndianapolis To Austin Multiple Airlines airfares from Indianapolis in August
$352 Depart: 08/28/2021
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$2541 Depart: 05/17/2022
Return: 05/31/2022

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$164 Depart: 07/13/2022
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Alaska AirlinesOklahoma City To Chicago Alaska Airlines airfares from Oklahoma City in September
$440 Depart: 09/12/2021
Return: 09/21/2021

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Multiple AirlinesDurham To Barcelona Multiple Airlines airfares from Durham in July
$1237 Depart: 07/29/2022
Return: 08/08/2022

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Multiple AirlinesChicago To Saint Louis Multiple Airlines airfares from Chicago in December
$267 Depart: 12/08/2021
Return: 12/28/2021

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