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 $126 / RT details

Book your flight now with FlyFar and save!

Cheap Chicago airfares from $126/RT are provided by FlyFar. Outbound flight is leaving on 11/30/2017, 05:05 am from Boston Logan (BOS) airport and arrives at Chicago Midway (MDW) at 06:55 am. The flight time is 1 hours and 50 minutes. The Returning flight departes on 12/07/2017, 07:40 am (other return dates are also available). Date posted: 23 Nov 2017

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

  • $126Major Airline flight Major Airline 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)11/30/201705:05 am
    Chicago, IL (MDW)Boston, MA (BOS)12/07/201707:40 am
    flyfar.ca check price
  • $129Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (MDW)11/30/201705:05 am
    Chicago, IL (MDW)Boston, MA (BOS)12/07/201707:40 am
    flightnetwork.com check price
  • $152Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)01/17/201805:03 pm
    Chicago, IL (ORD)Boston, MA (BOS)01/31/201809:40 am
    flighthub.com check price
  • $159United Airlines flight United Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)11/30/201706:20 am
    Chicago, IL (ORD)Boston, MA (BOS)12/07/201701:45 pm
    flighthub.com check price
  • $159Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)11/29/201707:00 am
    Chicago, IL (ORD)Boston, MA (BOS)12/06/201709:40 am
    cheapoair.com check price
  • $49Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)12/05/201712:25 pm
    cheapoair.com check price
  • $50Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)12/05/201705:10 pm
    flighthub.com check price
  • $59Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)12/10/201707:00 am
    flighthub.com check price
  • $79United Airlines flight United Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)12/05/201706:10 pm
    flighthub.com check price
  • $79United Airlines flight United Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)12/10/201709:10 am
    flighthub.com check price
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Know what to do when flying to Chicago?

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