Best 195 things to do in Chicago, IL

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 essential sea kayaking skills with certified instructors

Learn paddleboard skills for calm-water adventures

Cruise Chicago’s lakefront in an exotic vehicle with skyline and landmark views

Cruise Chicago on a 10-mile Lamborghini Urus ride

See Chicago landmarks from the back seat of a Rolls-Royce with a private driver

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

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

Eat Chicago’s five classic dishes with VIP access in River North and Streeterville

Ride a foodie bus to restaurants seen in The Bear, with tastings along the way

Eat your way through Chicago’s Chinatown with 5 seated tastings

Walk Pilsen for tacos, cocktails, and mural-filled streets

Private yachting for celebrations, family gatherings, and corporate outings

Charter a 48 ft Sea Ray Flybridge for up to 13 guests on Lake Michigan

Private Sea Ray yacht charter on Lake Michigan with 3–8 hour options

Private 37' Sea Ray Sundancer cruise for up to 13 guests

Cruise on a 46 ft Sea Ray Express with up to 13 guests

Cruise Chicago by private boat on a 50 ft Sea Ray Sundancer, up to 13 guests

Host a private celebration aboard a Hamptons-inspired catamaran