Best 252 things to do in Oakbrook Terrace, IL

Paddle Lake Michigan’s shoreline for city views and guided instruction

Pilot a 2-person Craig Cat and cruise the Chicago River skyline

Paddle the Chicago River and learn downtown architecture in 3 hours

Night kayak tour to watch Navy Pier fireworks

Paddle the Chicago River past the Wild Mile and downtown skyline

Choose your paddlecraft for a self-guided outing on the water

Paddle past the Wild Mile and Chicago's skyline in a single or double kayak

Explore Chicago River routes by kayak or stand-up paddleboard at your own pace

Paddle Chicago River routes in a single or double kayak

Paddle the Chicago River in a single or double kayak, from the Wild Mile toward downtown

Build foundational kayaking skills on calm Chicago River waters

Learn paddleboard skills for calm-water adventures

Paddle Goose Island and downtown as Chicago lights reflect on the river

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

Trace Chicago’s Prohibition history across four neighborhood speakeasies

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

Sail Lake Michigan with Chicago skyline views

Share a peaceful Lake Michigan sail with Chicago skyline views

A quiet private weeknight sail with Chicago skyline views

Sail Lake Michigan on a private weeknight cruise with sunset and skyline views

Taste donuts and beignets while uncovering New Orleans history on foot

Taste changing donut selections and discover California's donut culture

Taste local donuts while uncovering the history of Washington, DC

Taste island sweets while exploring Old Town with a local guide