Best 153 things to do in Wilmette, IL

Cruise with up to 12 guests and relax, dine, and swim on the water

Sail Lake Michigan privately with Chicago skyline views

Sail Lake Michigan together and take in Chicago’s skyline on a private weekend charter

Sail Lake Michigan at sunset on a private weeknight charter for two

Private weeknight sail for up to six guests with Lake Michigan skyline views

Anchor at Chicago’s Playpen for swimming, skyline views, and lakeside relaxation

Fish Lake Michigan on a private charter with a 100-ton Master Captain

See Chicago’s lighthouse, Navy Pier, and skyline from the water

Cruise about two miles offshore for wide-open Chicago sunset views

Speed across Lake Michigan with your own music and skyline views

Cruise offshore from Navy Pier for fireworks and skyline views

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

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

Eat a donut, then head up to the Willis Tower Skydeck

Walk the Chicago Loop to see hidden interiors and Millennium Park

Cruise the Chicago River on a private boat with local architecture stories

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

Cruise the Chicago River in a charming 1950s Milo Craft

Paddle the Chicago River after dark with skyline reflections

Paddle Lake Michigan’s shoreline with guided Chicago skyline views

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