Day 1 gets you your bearings; Day 2 is where downtown Chicago really opens up. The trick is the order you do things in — walk it this way and you'll skip driving in loops and fighting the Loop's traffic. Here's the exact route I run people through.
Start at the Museum Campus
Kick off at the Shedd Aquarium, then drive (or walk) out to the Adler Planetarium — the little peninsula there is the best free skyline photoshoot in the city. From there it's a short hop to Grant Park and the Buckingham Fountain.
Culture, then the icons
Duck into the Chicago Cultural Center for the largest Tiffany stained-glass dome in the world (and it's free). Then the Art Institute, the Crown Fountain, Cloud Gate — 'the Bean' — and the Millennium Monument, all within a few minutes of each other.
Indian tip: cross the road at the Bean and head into Millennium Station — there's a small bar with an Indian spot right next to it. Grab your drinks at the bar and order samosas and snacks from the little window counter opposite. Nobody tells you about this one.
Eat around the Bean
You're spoiled here: Wildberry Pancakes for breakfast, Stan's Donuts, Giordano's for deep dish, Nando's Peri-Peri, Nutella Café, Naf Naf, Halal Guys. Pick your fighter.
West, then the river and the lake
Three blocks west of the Bean is Daley Plaza and Picasso's 50-foot untitled sculpture. Head north on Clark toward Wacker, and two blocks east you'll hit LondonHouse — go up to the rooftop for the best downtown view and a proper cocktail. Cross the road and you're on the Chicago Riverwalk; follow it (walk, cycle, or Uber) out to Navy Pier, with Willis Tower and Union Station on your radar.
Finish like a local
Rent a bike and do a lakefront-and-downtown cycle loop — genuinely worth it (try Groupon). Then end the day at a local tavern with a Chicago hot dog: Superdawg, Red Hot Ranch, Fatso's Last Stand or Kim & Carlo's.
