With kids, give The Second City a miss.
A sketch revue at the birthplace of modern improv is a genuine bucket-list comedy night — but which room you book changes the experience. The Mainstage revue is the polished, scripted-and-improvised flagship and the safest bet; the smaller e.t.c. stage runs an edgier, more experimental revue; and the late-night and free improv sets after the revues are looser, hit-or-miss, and where you actually watch unscripted improv being built. The honest catch is variability — it's live, so any given night swings — and it's an evening-out-with-drinks commitment, not a daytime sight.