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 $147 / RT details

Book your flight now with Cheapoair.com and save!

Cheap Chicago airfares from $147/RT are provided by Cheapoair.com. Outbound flight is leaving on 05/22/2018, 12:45 pm from Boston Logan (BOS) airport and arrives at Chicago O`hare (ORD) at 02:31 pm. The flight time is 1 hours and 46 minutes. The Returning flight departes on 06/06/2018, 02:10 pm (other return dates are also available). Date posted: 04 Mar 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

  • $147Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)05/22/201812:45 pm
    Chicago, IL (ORD)Boston, MA (BOS)06/06/201802:10 pm
    cheapoair.com check price
  • $148Major Airline flight Major Airline 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)05/22/201809:20 am
    Chicago, IL (MDW)Boston, MA (BOS)05/30/201812:05 pm
    flyfar.ca check price
  • $153Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)05/22/201809:20 am
    Chicago, IL (MDW)Boston, MA (BOS)05/30/201812:05 pm
    flightnetwork.com check price
  • $157Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)05/29/201812:45 pm
    Chicago, IL (ORD)Boston, MA (BOS)06/05/201802:10 pm
    cheapoair.com check price
  • $158Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)08/14/201812:45 pm
    Chicago, IL (ORD)Boston, MA (BOS)08/22/201802:10 pm
    cheapoair.com check price
  • $55Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)05/30/201812:45 pm
    cheapoair.com check price
  • $55Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)06/19/201808:35 pm
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  • $76Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)05/30/201807:25 am
    cheapoair.com check price
  • $82Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)06/19/201812:45 pm
    cheapoair.com check price
  • $90Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)05/24/201812:45 pm
    flightnetwork.com check price
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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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