Looking for the best things to do in Chicago? Locals send first-timers to Millennium Park and Cloud Gate (“The Bean”), the Art Institute of Chicago, an architecture river cruise, a skydeck view from Willis Tower or 360 Chicago, and the lakefront Museum Campus — with deep-dish and Italian beef along the way. Here’s how Chicagoans actually spend their time, by neighborhood, by night, by budget, and by who you’re with.
Things to do in Chicago, by neighborhood
The Loop & Millennium Park
Downtown’s core: Cloud Gate (“The Bean”), Maggie Daley Park, the Art Institute, the Riverwalk, and the start of most architecture boat tours.
River North & Magnificent Mile
Galleries, rooftop bars, and the Mag Mile shopping strip up Michigan Avenue toward the historic Water Tower.
West Loop
Chicago’s dining destination — Restaurant Row on Randolph Street — plus Fulton Market bars and galleries.
Lincoln Park & Lakeview
The free Lincoln Park Zoo, conservatory and lakefront, plus Wrigleyville and Wrigley Field to the north.
Museum Campus
Three greats on the lake: the Field Museum, Shedd Aquarium, and Adler Planetarium, with skyline views back toward downtown.
Things to do in Chicago at night
Rooftops and dining in River North and the West Loop, comedy at The Second City, blues and jazz clubs, and a night game in Wrigleyville. A riverwalk or lakefront stroll shows the skyline at its best.
Indoor & rainy-day (and winter) things to do in Chicago
Chicago does indoors better than almost anywhere: the Art Institute, Field Museum, Shedd Aquarium, Museum of Science and Industry, the free Chicago Cultural Center, and the Willis Tower Skydeck. The Mag Mile covers indoor shopping.
Free things to do in Chicago
- Millennium Park and Cloud Gate (“The Bean”)
- Lincoln Park Zoo (free admission)
- The Lakefront Trail and beaches
- The Garfield Park Conservatory
- The Chicago Cultural Center and Maggie Daley Park
Things to do in Chicago for couples
The architecture river cruise, sunset from a skydeck or rooftop, a Riverwalk stroll, Millennium Park, and dinner on West Loop’s Restaurant Row make a great date day into night.
Things to do in Chicago with kids
Family wins: Shedd Aquarium, the Field Museum, the Museum of Science and Industry, Lincoln Park Zoo, Navy Pier, and Maggie Daley Park.
What Chicago locals actually recommend
Which deep-dish is worth it (and which is for tourists), which neighborhoods are worth your afternoon, where to catch music without the crowds — that comes from people who live here. On Neighborhood Nurturers’ Chicago community, real Chicago neighbors answer “what should I actually do this weekend?” and share the local spots the guidebooks miss. Join your Chicago neighbors free →
Frequently asked questions
What are the top things to do in Chicago?
Locals start visitors at Millennium Park and Cloud Gate (‘The Bean’), the Art Institute of Chicago, an architecture river cruise, the Willis Tower or 360 Chicago skydeck, and Navy Pier — then send them for deep-dish and an Italian beef. The Museum Campus (Field, Shedd, Adler) is a full day on its own.
What is there to do in Chicago at night?
Chicago nights range from rooftop bars in River North and dining in the West Loop to comedy at The Second City, blues and jazz clubs, and a Cubs game in Wrigleyville. A lakefront or river walk after dark shows off the skyline.
What can you do in Chicago when it rains (or it’s cold)?
World-class indoor options: the Art Institute, the Field Museum, Shedd Aquarium, the Museum of Science and Industry, the free Chicago Cultural Center, and Willis Tower’s Skydeck. The Magnificent Mile and Water Tower Place cover indoor shopping.
What are free things to do in Chicago?
Plenty: Millennium Park and The Bean, the Lincoln Park Zoo (free), the Lakefront Trail, the Garfield Park Conservatory, the Chicago Cultural Center, and Maggie Daley Park. Summer brings free festivals and concerts at Millennium Park.
What are the best things to do in Chicago for couples?
Take the architecture river cruise, walk the Riverwalk, watch sunset from a skydeck or rooftop, stroll Millennium Park, and book a table on West Loop’s Restaurant Row.
What are fun things to do in Chicago with kids?
Family favorites include Shedd Aquarium, the Field Museum, the Museum of Science and Industry, Lincoln Park Zoo, Navy Pier, and Maggie Daley Park’s play garden.