Best 301 things to do in Chicago, IL

Take in Chicago’s skyline from a floating tiki bar with a full bar on board

See Chicago by water from a floating tiki bar with Sunday drink specials

Cruise Chicago’s waterways aboard a floating tiki bar with Sunday drink specials

Taste five Chicago specialties while exploring River North’s history and architecture

Celebrate on an 80-foot yacht with an included open bar

Private Chicago river and lake charter with an included open bar

Cruise Chicago’s river and lake skyline aboard a private two-deck party boat

Ride a new 2026 Yamaha cruiser along Chicago's lakefront

Walk Chicago’s Pedway and spot hidden details in the Loop

Walk the Loop to see Chicago’s hidden interior architecture

Taste four pizza styles on a 3-hour downtown Chicago walk

Taste Chicago pizza on a guided bus tour with 4 neighborhood stops

Trace Chicago’s Prohibition history across four neighborhood speakeasies

Step inside Chicago Loop landmarks and trace the evolution of its skyline

Private skyline cruise with a local perspective

Trace Chicago's skyscraper story with a donut tasting

Explore Chicago's Prohibition era through stories of class, nightlife, and rebellion

Taste international dough-based treats while exploring Wynwood’s art district

Taste Santa Monica’s donut culture on an outdoor walking tour

Taste Dublin’s doughnuts while uncovering city stories on foot

Walk Edinburgh’s Old Town and sample doughnuts and pastries in 2 hours

Taste Chicago’s donuts while uncovering the city stories behind each shop

Ride in a 2-seat supercar and capture your Chicago photo moment

See major works with an art historian guide in a small group