things to do in Chicago, IL

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

Make a fall favorite from scratch and take a box of donuts home

Cruise the Chicago River for skyline views and Riverwalk sights

Help shape an alien conspiracy story made up live on stage

Discover Chicago beyond its familiar sights

Eat your way through Uptown’s immigrant neighborhoods in 2.5 hours

See Chicago landmarks from the water on a private sightseeing outing

Explore Chicago through social adventures with fellow solo travelers

Cruise Chicago waters with up to 13 guests for a flexible three-to-four-hour outing

Discover Chicago architecture and fireboat history on a guided river cruise.

Paddle the Chicago River past the Wild Mile and downtown skyline

Take the wheel on a 22 ft pontoon cruise on the Chicago River

Paddle Lake Michigan with Chicago skyline views

See Chicago fireworks from a floating tiki bar on Lake Michigan

Build sourdough skills and take home starter, bread, and dough for your next bake

Sail Lake Michigan on a private day charter with skyline views

Explore Lake Michigan’s quieter shore, from lakeside towns to grand mansions

Taste Vietnam, the Middle East, and Sweden while exploring Argyle and Andersonville with a guide

Photograph Chicago's skyline from a US Navy-built boat

Pedal Chicago’s top sights while tasting pizza, hot dogs, and Italian beef

Private yachting for celebrations, family gatherings, and corporate outings

2-hour happy hour cruise with skyline views and a full bar

Paddle the Chicago River and learn downtown architecture in 3 hours

Anchor at Chicago’s Playpen for swimming, skyline views, and a laid-back day on the water