Cheap flights from Boston to Chicago

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Travel tip: Visit Chicago on your holidays!

Check our current prices for flights from Boston to Chicago. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Boston to Chicago, you will need to run a search below.

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From $142 / RT details

Book your flight now with Cheapoair.com and save!

Cheap Chicago airfares from $142/RT are provided by Cheapoair.com. Outbound flight is leaving on 01/29/2019, 08:55 pm from Boston Logan (BOS) airport and arrives at Chicago O`hare (ORD) at 10:51 pm. The flight time is 1 hours and 56 minutes. The Returning flight departes on 02/12/2019, 09:06 am (other return dates are also available). Date posted: 20 Dec 2018

Price evolution for flights From Boston To Chicago

Price overview for flights from Boston to Chicago

Recent Deals on Flights from Boston to Chicago:Roundtrip / Oneway

  • $142Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)01/29/201908:55 pm
    Chicago, IL (ORD)Boston, MA (BOS)02/12/201909:06 am
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  • $142Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)01/31/201908:55 pm
    Chicago, IL (ORD)Boston, MA (BOS)02/10/201905:40 am
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  • $142Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)03/19/201909:03 pm
    Chicago, IL (ORD)Boston, MA (BOS)03/27/201908:45 am
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  • $143Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)03/05/201912:15 pm
    Chicago, IL (ORD)Boston, MA (BOS)03/14/201908:45 am
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  • $152Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)03/05/201912:15 pm
    Chicago, IL (ORD)Boston, MA (BOS)03/14/201908:45 am
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  • $71Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)02/12/201906:26 am
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  • $71Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)01/31/201908:55 pm
    cheapoair.com check price
  • $71Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)02/13/201906:26 am
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  • $81Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)03/08/201905:00 am
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  • $81Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)02/13/201905:45 am
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Know what to do when flying to Chicago?

Chicago Travel Guide 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. Though [...]
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