Best 205 things to do in Deerfield, IL

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

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

Walk the Loop to see Chicago’s hidden interior architecture

Walk Chicago’s dark history in 2 hours, from gangsters to ghost lore

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

Design your own Chicago lakefront day aboard Soulshine

Ride a new 2026 Yamaha cruiser along Chicago's lakefront

Sail Lake Michigan for views of Chicago’s shoreline and skyline

Live blues, Lake Michigan sailing, and Chicago skyline views

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

Cruise out for Navy Pier fireworks with skyline views and bar service

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

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

Tropical river views, island tunes, and a full bar in Chicago

Take in Chicago’s skyline from a floating tiki bar with a full bar on board

See Chicago by water from a floating tiki bar with Sunday drink specials

Cruise Chicago’s waterways aboard a floating tiki bar with Sunday drink specials