On select Date in October and November, United Airline has flight between Chicago (ORD) and BOSTON (BOS) for $91 nonstop roundtrip. This is a basic economy fare. There are a lot of restrictions on carryon, checked bag, seating and boarding priority. Please check united website to be sure
Late October to Early November , Monday- Thursday with a weekend stay.
Sample Date: 11/1 – 11/7