Best 315 things to do in Northbrook, IL

Step inside Chicago’s Art Deco buildings on a 2-hour Loop walk

Follow a festive downtown trail of landmark trees, traditions, and indoor holiday displays

Private 1962 vintage motorboat cruise on the Chicago River for up to 6 guests

Cruise Chicago’s waterfront with a professional crew and private gathering spaces

Celebrate on the Gypsy Spirit along Chicago’s waterfront

Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board

Private Lake Michigan sailing with swimming, snacks, and a certified captain

Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht

A private sail for proposals, photos, and a champagne toast

Design your own Chicago lakefront day aboard Soulshine

Ride a new 2026 Yamaha cruiser along Chicago's lakefront

Make an entrance in a 2024 Tesla Cybertruck for your next Chicago outing

Sail Lake Michigan for sweeping views of Chicago’s skyline

See Chicago’s skyline from Lake Michigan on an evening sail

Watch Navy Pier fireworks from the water with Chicago skyline views

90-minute group sail for Navy Pier fireworks and Chicago skyline views

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

Feel the raw power of a 707-horsepower American muscle sedan

Cruise Chicago on a 10-mile Lamborghini Urus ride

Feel Porsche handling in an all-wheel-drive electric sedan

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

Twin-turbo V8 performance with grand-touring comfort

Drive a seven-passenger performance SUV with leather, wood, and all-wheel drive

Twin-turbo V8 performance with a 7-speed automatic transmission