The Second City is the leading brand in improv-based sketch comedy and one The James Chicago's official Cultural Collection partners. The Second City is one of Chicago’s most prominent cultural entities, as the country’s newest crops of celebrity comics tend to come out of Chicago.

The James was the exclusive hotel partner of The Second City’s All Star Comedy Benefit, which benefitted Gilda’s Club and hosted celebrity attendees including Aidy Bryant, Fred Willard, Tim Meadows, among others.

The Second City is also a part of The James “Curated Meeting Break” program, which any group who books a meeting or an event can select for a much needed breather. The Second City curated meeting break includes a trained improv performer who will come to The James and give tips and suggestions using improve techniques on public speaking and presentation giving that help to motivate and build confidence in attendees.