Tis the season when Chicago’s stages give way to Ebenezer Scrooges, George Baileys and Nutcracker princes — plus, the sounds of klezmer, flamenco, bluegrass and Motown.

It’s not a milestone year, but the kickoff to Hubbard Street’s 48th season sure feels like it, with a program spanning five decades in under two hours — all from within the company’s ...