Best 301 things to do in Chicago, IL

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

See Art Institute Masterpieces With an Art Historian

See Chicago’s public art and landmark architecture with an expert guide

Explore Art Institute masterpieces with a private art historian

Trace Chicago's skyline story through Loop landmarks

Sail Chicago’s skyline aboard an 80-foot tiki-chic yacht

Private yacht charter with an included open bar and skyline charter option

Ride Chicago’s 1920s–30s gangster trail with actor guides

Island tunes, skyline views, and a full bar on the Chicago River

Celebrate on a tiki-themed yacht with an open bar and Chicago skyline views

Cruise the Chicago River aboard a private floating tiki bar

Trace Chicago's haunted lore, gangster history, and true-crime disasters on foot

Private 1962 vintage motorboat cruise on the Chicago River for up to 6 guests

Tour and tasting for two with a tasting room reservation and wine

Private 50-foot charter with two decks, a waterslide, and an open bar

Taste your way through Chicago’s West Loop with a local guide

Design your own Chicago lakefront day aboard Soulshine

Taste Chicago donuts while uncovering Fulton Market’s industrial past

Cruise Chicago’s lake and river on a historic fireboat with docent-led stories

Walk Chicago’s must-see sights, including Millennium Park, in 2 hours

Bike Miami Beach and sample local food with a guide

Bike and taste your way through Miami Beach’s Art Deco streets and local eats

Taste Chicago classics and discover the stories behind the city’s signature dishes

Paddle Lake Michigan from Ohio Street Beach for two hours