Best 317 things to do in Deerfield, IL

Cruise the Chicago River aboard a private floating tiki bar

Walk Chicago’s Pedway and spot hidden details in the Loop

Walk the Loop to see Chicago’s hidden interior architecture

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

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

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

Celebrate on the Gypsy Spirit along Chicago’s waterfront

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

Trace Chicago's skyscraper story with a donut tasting

Sail Lake Michigan for sweeping views of Chicago’s skyline

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

Sail Chicago’s skyline aboard an 80-foot tiki-chic yacht

Private yacht charter with an included open bar and skyline charter option

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