A weekend in Chicago
How to spend a weekend in Chicago — the architecture, the lakefront, Millennium Park’s Bean, world-class museums and deep-dish pizza.
Chicago rewards a weekend: a walkable core on the shore of Lake Michigan, the skyline that invented the skyscraper, and a food scene that goes far beyond deep-dish. Here is a two-day plan.
Day one — downtown & the lakefront
- Start in Millennium Park at Cloud Gate (“the Bean”), then walk the lakefront to the Art Institute of Chicago.
- Take an architecture river cruise — the single best way to understand the city — from the Chicago Riverwalk.
- Go up the Willis Tower Skydeck or 360 Chicago for the view, then dinner in the West Loop’s Restaurant Row.
Day two — neighbourhoods
- Wander Wicker Park and Bucktown for boutiques, coffee and street art, or Pilsen for Mexican food and murals.
- In summer, catch a Cubs game at Wrigley Field in Lakeview; year-round, the Museum of Science and Industry is worth the trip south.
Getting around & when to go
The “L” train (including the Blue Line from O’Hare) and buses cover the city cheaply with a Ventra card. Late spring to early autumn is the sweet spot — winters are genuinely cold and windy off the lake. Find places to stay in Chicago and New York.