Chicago — Sights
Skyscrapers over the river, deep dish in hand
- Millennium Park & Cloud Gate (The Bean) — A giant silver bean with the whole skyline bent across it
- Art Institute of Chicago — American Gothic and Nighthawks, in the flesh
- Chicago Architecture Center River Cruise — A 90-minute boat ride past the city's best buildings, with stories
- Willis Tower Skydeck (The Ledge) — Stand in a glass box 103 floors up, 412 m of air under your feet
- 360 CHICAGO Observation Deck (TILT) — A 94th-floor lakeside deck that stays open till 11pm
- Navy Pier — A kilometre-long pier and a Ferris wheel facing the skyline
- The Magnificent Mile — Chicago's showpiece avenue, from Gothic towers to flagship stores
- Chicago Riverwalk — A 2 km path at water level beneath a canyon of towers
- Field Museum — Home of SUE, the most complete T. rex ever found
- Shedd Aquarium — Beluga whales swimming against a backdrop of Lake Michigan
- Adler Planetarium Skyline View — A free spot with the entire skyline across the water
- Lincoln Park Zoo — Free every day of the year, right beside the skyline
- Wrigley Field Tour — Ivy walls and a hand-turned scoreboard in a 100-year-old ballpark
- The 606 & Wicker Park — An old elevated rail line turned trail, plus vintage-shop streets
- Garfield Park Conservatory — A 1908 glasshouse jungle, T-shirt warm even in January
- Jazz & Blues Club Night (Green Mill, Buddy Guy's Legends) — Al Capone's old jazz bar and a blues legend's club
- Chicago Cultural Center — A free palace under a Tiffany glass dome
- Museum of Science and Industry — A real U-boat and real trains under one roof
- Frederick C. Robie House — Wright's horizontal Prairie masterpiece
- Frank Lloyd Wright Home and Studio (Oak Park) — The house where Wright lived and worked, a train ride away
- The Second City — An evening in the birthplace of improv comedy
- The Chicago Theatre — The red CHICAGO sign over State Street
- Lincoln Park Conservatory — A free Victorian glasshouse that stays green in winter
- Maggie Daley Park — Skating ribbon and climbing gardens by the lake
- Museum of Contemporary Art Chicago — Contemporary art with a sculpture garden near the lake
- North Avenue Beach — A sand beach with the skyline at its back