Bust a gut at a comedy show
Chicago has a comprehensive comedy circuit, no doubt. It's easy to believe The Second City is THE place to take out-of-towners, and you wouldn't be entirely wrong for thinking this, but there are other venues worth scoping out for cutting-edge stand-up, improv, and sketch acts, like iO Chicago, Zanies Comedy Club, pH Comedy Theater, and ComedySportz Theatre.
Uncover Chicago's history through its breathtaking backdrop
With its world-renowned architecture, Chicago's obvious go-to tour involves the stories behind its vast array of iconic buildings, and sometimes the best way to see it all is by river. If crossing intersections in the city with your slow-poke family in tow gives you hives just thinking about it, book one of the Chicago Architecture Foundation’s First Lady River Cruises and pack their brains with all legendary stuff without having to wait through any traffic lights.