Cheap flights from Boston to Chicago, United States (BOS - CHI)

As a rule, buying flight tickets from Boston to Chicago expends a lot. Using our service of searching for cheap flight tickets, you will be able to save a significant sum of money! We will help tip to buy flight tickets from Boston to Chicago at the most favorable prices.

Out service helps you to find tickets from Boston to Chicago in the most reliable travel agencies and booking systems, including all the airline companies. We don't sell tickets and don't do any surcharges, we just find the best offers - you choose yourself where you want to buy flight tickets Boston - Chicago at the best price!

We also recommend you to look through the prices for return tickets from Chicago to Boston.

Airfares found by our users in the past 24 hours

The cheapest flight from Boston to Chicago is $100 on JetBlue Airways, departing on 25.05.2025 and returning on 29.05.2025.
The price for these dates could change. Use search to get the best price.
AirlineDeparture dateReturn datePrice
JetBlue Airways25.05.202529.05.2025from $100

Average round-trip airfares from Boston to Chicago by months

MonthRound-Trip
April 202530.04 - 04.05from $132
May 202525.05 - 29.05from $100
June 2025find now
July 202507.07 - 10.07from $132
August 2025find now
September 2025find now
October 2025find now
November 2025find now
December 2025find now
January 2026find now
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March 2026find now

The price which were found by our clients for the latest several days. Given ticket prices could change. It's connected with the presence of flight tickets while booking.

Airlines are flying from Boston to Chicago

Southwest Airlines
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