Lakefront & Art Institute

Start at Cloud Gate (The Bean) — take the obligatory selfie, then walk through Lurie Garden. In summer, catch a free concert at Pritzker Pavilion.

2 min walk. World-class museum — Seurat's A Sunday Afternoon, Hopper's Nighthawks, and the modern wing are must-sees. One of the best art museums in the world.

5 min walk. Rooftop restaurant atop the Chicago Athletic Association Hotel with sweeping views of Millennium Park and the lake. Book a window table.

10 min walk. Cocktails 95 floors up in the John Hancock Center. Skip the Skydeck — this view is better and comes with a drink.