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Boston (BOS) » United States » BOS to ORD
Good to Know - Flights from Boston to Chicago
$ 138.98
or less (round trip)
Top Tips for Finding Cheap Flights from Boston to Chicago
Looking for cheap airfare from Boston to Chicago? 25% of our users found round-trip tickets to Chicago for the following price or less: $ 138.98 Book at least 4 weeks before departure in order to get a below-average price. Enter your preferred departure airport and travel dates into the search form above to unlock the latest Boston to Chicago flight deals.
FAQs - Booking from Boston to Chicago flights
The cheapest flight Boston to Chicago found on flyus.com in the last 72 hours was $138.98 round-trip.
Find cheap flights from Boston to Chicago and book discounted airfare from different cities all over the United States. Explore airline ticket deals on flight routes all over the World! At Flyus, we take pride in helping you discover and book the best flight deals for your next trip at the cheapest price. We make booking flights from different departures easy and provide you with peace of mind with our Best Purchase Guarantee.
Cheapest Flights
from Boston, United States (BOS) to:
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Chicago, United States (ORD)May 13, 25 - May 20, 25$138.98
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Chicago, United States (ORD)Feb 08, 25 - Feb 10, 25$156.19
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Chicago, United States (ORD)Jan 28, 25 - Feb 04, 25$156.19
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Chicago, United States (ORD)Jan 23, 25 - Jan 27, 25$156.19
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Chicago, United States (ORD)Jan 14, 25 - Jan 16, 25$156.19