Best 158 things to do in Chicago, IL

Paddle the Chicago River after dark with city lights and stories from your guide

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

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

Cruise Chicago on a 10-mile Lamborghini Urus ride

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

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

Private 6–8 hour fishing charter for up to 6 on Lake Michigan

Sail Lake Michigan for Navy Pier fireworks views on a private charter