Chicago After Dark

Chicago is one of the best cities in the country for a dinner experience — and it's not a close call. The improv tradition runs deep here (Second City is around the corner from half these venues; it shows in the actors), the hotel ballrooms are genuinely impressive, and unlike New York, nobody's charging you $200 for the privilege of a view of a parking garage. The lake helps too.

The murder mystery scene is anchored by two serious operators: The Dinner Detective, running every Saturday at the Millennium Knickerbocker Hotel — a 1927 landmark on the Magnificent Mile with a documented Al Capone connection — and The Murder Mystery Company doing public shows in Arlington Heights, 25 miles northwest of the Loop with free parking. The dinner cruise scene splits between the Chicago River (more urban, better for first-timers) and Lake Michigan (more dramatic, noticeably more expensive). Medieval Times is in Schaumburg — 45 minutes from downtown, which is either a dealbreaker or a reason to make a whole night of the suburbs.

What sets Chicago's experiential dining scene apart is the quality floor. The budget options here are run by professionals. You'd genuinely have to work hard to have a bad time.