A three-stop low-key night in Magnificent Mile — good food, somewhere easy, home at a reasonable hour. Built from real venues, in walking order.
Eat first — it settles the group and gives the night somewhere to begin.
The high point. Everything before this builds up to it; everything after eases off.
Somewhere quieter to land, so the night ends instead of just stopping.
Stops are real venues, ordered so the night builds and then eases off — food first, one high point, somewhere quieter to finish. Times assume about 15 minutes between stops, which is a short walk at this scale.