My boyfriend surprised me with tickets to a show called The Frog Bride at the Hanna Theatre this spring.
It's a smaller theater, but with loads of historical charm. When we went, there was a large bar at the top of the theater, where you can buy wine and beer (rather pricey, I might say) before sitting down in your seats. I can't wait to attend more shows at this theatre. It has that small, history-driven feel that makes you want to go back for me, even just to check out the layout, and brush up on some facts.
Love the theater district. Love Playhouse Square. Love the Hanna Theatre.