Best 184 things to do in Chicago, IL

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

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

Celebrate, cruise, and swim aboard a 52-foot Sea Ray

Relax together with a flybridge lounge, wide walkways, and onboard music

Set your own pace on a private Chicago yacht cruise

Charter a 47’ Carver yacht with kitchen, bathrooms, and Bluetooth audio

Set sail aboard a 50' Sea Ray with a kitchen, bathrooms, and Sonos audio

Cruise a 47-foot Carver with space to relax, dine, and play your music