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Good to Know - Flights from Boston to Chicago

Good Deal:
$ 156.19
or less (round trip)

Cheapest Day of the Month to Book Flights



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: $ 156.19 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

What is the cheapest flight Boston to Chicago?:
The cheapest flight Boston to Chicago found on flyus.com in the last 72 hours was $156.19 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.

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Cheapest Flights
from Boston, United States (BOS) to:

  • Chicago, United States (ORD)
    Jan 23, 25 - Jan 24, 25
    $156.19
    Search

  • Chicago, United States (ORD)
    Jan 13, 25 - Jan 19, 25
    $156.19
    Search

  • Chicago, United States (ORD)
    Jan 30, 25 - Feb 02, 25
    $156.19
    Search

  • Chicago, United States (ORD)
    Jan 11, 25 - Jan 19, 25
    $156.19
    Search

  • Chicago, United States (ORD)
    Jan 18, 25 - Jan 19, 25
    $156.19
    Search