Chicago 3-Day Itinerary

This plan works best from late spring to early autumn. In winter, swap the outdoor parts for more time in museums, and keep the river cruise for the warmer months, when it runs.

Day 1: The river and the Loop

Take a morning architecture river cruise, then follow our Loop walking route past the Rookery and the Monadnock. Lunch on an Italian beef. In the late afternoon, walk through Millennium Park to see Cloud Gate and the Crown Fountain, then eat deep dish or tavern-style pizza in River North.

Day 2: Art and the lake

Spend the morning at the Art Institute, with the plan from our museums guide. After lunch, walk south along the lake to the Museum Campus, choose the Field Museum or the Shedd, and finish on the path out to the Adler Planetarium for the skyline view. Dinner in the West Loop.

Day 3: Hyde Park or the North Side

Choose one. Head south to Hyde Park for the Obama Presidential Center, the Museum of Science and Industry and the Robie House. Or go north: Lincoln Park Zoo, a walk along the lakefront to North Avenue Beach and, in season, an afternoon game at Wrigley Field. In the evening, find a blues club or a rooftop bar, and see the skyline lit up from Willis Tower or 360 Chicago.

With more time

Add Oak Park's Frank Lloyd Wright houses, tacos and murals in Pilsen, or a lazy lake day. Our food guide has ideas for every neighbourhood.