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 $226 / RT details

Book your flight now with Cheapoair.com and save!

Cheap Chicago airfares from $226/RT are provided by Cheapoair.com. Outbound flight is leaving on 01/11/2022, 10:46 am from Boston Logan (BOS) airport and arrives at Chicago O`hare (ORD) at 03:00 pm. The flight time is 4 hours and 14 minutes. The Returning flight departes on 01/26/2022, 07:05 am (other return dates are also available). Date posted: 16 Aug 2021

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

  • $226Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)01/11/202210:46 am
    Chicago, IL (ORD)Boston, MA (BOS)01/26/202207:05 am
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  • $339Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)11/30/202110:46 am
    Chicago, IL (ORD)Boston, MA (BOS)12/08/202107:05 am
    cheapoair.com check price
  • $349Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)01/11/202210:46 am
    Chicago, IL (ORD)Boston, MA (BOS)01/26/202206:55 pm
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  • $482Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)11/30/202110:46 am
    Chicago, IL (ORD)Boston, MA (BOS)12/08/202106:55 pm
    cheapoair.com check price
  • $50Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)12/01/202105:29 pm
    cheapoair.com check price
  • $60Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)12/08/202105:45 am
    cheapoair.com check price
  • $71Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)02/16/202205:45 am
    cheapoair.com check price
  • $230Alaska Airlines flight Alaska Airlines 
    FromToDepartureTime
    Boston, MA (BOS)Chicago, IL (ORD)12/01/202107:10 am
    cheapoair.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 [...]
Chicago History The site where Chicago stands had long been considered as an important portage point on the water route linking the Great Lakes with the Mississippi river. Aside from this important fact, there are a lot of interesting things you need to know [...]
Chicago Sightseeing The rich cultural heritage of Chicago is depicted in its famous sights. Other tourist attractions in the city can be seen in zoos and parks as well. If you are thinking about visiting, it will help if you take a look at some of the travel [...]
Chicago Nightlife Chicago is one of the cities blessed with a variety of nightlife options. Discos, clubs, bars - name it and the place will certainly give you the pleasure you are looking for. You will surely dance the night away as you listen to the music [...]
Chicago Pictures
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  • cool site - Chicagoview
  • Chicago Limousine Bus - Chicagoview

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