Cheap flights from Chicago to Boston

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Travel tip: Visit Boston on your holidays!

Check our current prices for flights from Chicago to Boston. 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 Chicago to Boston, you will need to run a search below.

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From $143 / RT details

Book your flight now with Cheapoair.com and save!

Cheap Boston airfares from $143/RT are provided by Cheapoair.com. Outbound flight is leaving on 02/18/2019, 05:45 am from Chicago O`hare (ORD) airport and arrives at Boston Logan (BOS) at 09:04 am. The flight time is 3 hours and 19 minutes. The Returning flight departes on 02/23/2019, 08:59 pm (other return dates are also available). Date posted: 23 Jan 2019

Price evolution for flights From Chicago To Boston

Price overview for flights from Chicago to Boston

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

  • $143Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Boston, MA (BOS)02/18/201905:45 am
    Boston, MA (BOS)Chicago, IL (ORD)02/23/201908:59 pm
    cheapoair.com check price
  • $155Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Boston, MA (BOS)02/12/201907:00 am
    Boston, MA (BOS)Chicago, IL (MDW)02/21/201905:45 am
    flightnetwork.com check price
  • $160Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Boston, MA (BOS)02/12/201909:06 am
    Boston, MA (BOS)Chicago, IL (ORD)02/21/201908:59 pm
    cheapoair.com check price
  • $168Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Boston, MA (BOS)02/18/201905:45 am
    Boston, MA (BOS)Chicago, IL (ORD)02/23/201908:59 pm
    flightnetwork.com check price
  • $169Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Boston, MA (BOS)02/12/201909:06 am
    Boston, MA (BOS)Chicago, IL (ORD)02/21/201908:59 pm
    flightnetwork.com check price
  • $71Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Boston, MA (BOS)02/01/201907:51 pm
    cheapoair.com check price
  • $71Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Boston, MA (BOS)02/18/201905:45 am
    cheapoair.com check price
  • $71Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Boston, MA (BOS)02/17/201905:45 am
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  • $77Major Airline flight Major Airline 
    FromToDepartureTime
    Chicago, IL (MDW)Boston, MA (BOS)02/01/201907:00 am
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  • $81Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Boston, MA (BOS)02/01/201907:00 am
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Know what to do when flying to Boston?

Boston Travel Guide Boston is US nation's history and myth capital. It was, until 1755, the biggest city in America and the most directly affected by the British Crown (you can see that if you only consider that it has the same name as the city in UK). [...]
Boston History  On the 17th of September 1630, Boston was established by English Puritan colonists.  The Puritans are confused sometimes with Pilgrims, who established Plymouth 10 years before in what we know as Barnstable County, Plymouth County, and Bristol [...]
Boston Sightseeing  There are many things that you can see and do in Boston because of its historic and cultural background.  One of the many museums that you can visit is the Boston Museum of Fine Arts, which is a smaller version of the Metropolitan Museum of [...]
Boston Nightlife  There are many places that you can go to for enjoying nightlife in Boston, Massachusetts.  One of these is called Kings, offering a variety of activities and a diverse clientèle.  During the night, Kings brings a lengthy wait for tables and [...]
Boston Pictures
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