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 $96 on American Airlines, departing on 04.04.2025 and returning on 06.04.2025.
The price for these dates could change. Use search to get the best price.
AirlineDeparture dateReturn datePrice
American Airlines04.04.202506.04.2025from $96

Average round-trip airfares from Boston to Chicago by months

MonthRound-Trip
March 202528.03 - 31.03from $257
April 202504.04 - 06.04from $96
May 202524.05 - 25.05from $205
June 202517.06 - 18.06from $97
July 202501.08 - 03.08from $146
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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
Find Flights to Chicago