Cheap flights from Chicago to Boston

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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 / OW details

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Cheap airfares from /OW are provided by . This flight is going on , from () airport and arrives to () at so it makes 0 hours and 0 minutes. This is a oneway flight. Date posted: 31 Dec 1969

Price evolution for flights From Chicago To Boston

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

• $61 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (MDW)	Boston, MA (BOS)	04/12/2025	04:10 pm

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• $87 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Boston, MA (BOS)	04/12/2025	05:10 am

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• $158 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Boston, MA (BOS)	03/20/2025	07:07 pm

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• $190 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (MDW)	Boston, MA (BOS)	03/20/2025	04:45 pm

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• $391 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Boston, MA (BOS)	03/20/2025	11:55 am

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• We are sorry but currently there are no roundtrip offers for flights from Chicago to Boston.
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