things to do in Oak Park, IL

Take the wheel for open-air driving with smooth V12 power

Take the wheel for open-air cruising and a smooth ride

Get behind the wheel of a luxury SUV with military roots

Experience hybrid power and agile supercar handling

Explore Art Institute masterpieces with a private art historian

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

Walk the Loop to see Chicago’s hidden interior architecture

Trace Chicago's haunted lore, gangster history, and true-crime disasters on foot

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

See major works with an art historian guide in a small group

Relax together with a flybridge lounge, wide walkways, and onboard music

Set your own pace on a private Chicago yacht cruise

Double-decker catamaran for private entertaining and water views

Discover Lincoln Park’s nature and history with a local guide

Cruise the Chicago River for skyline views and Riverwalk sights

Sail Lake Michigan for Chicago skyline views and Navy Pier fireworks

Sail Chicago’s lakefront on a private charter with time to swim and relax

Sail Lake Michigan with Chicago skyline views

Sail Lake Michigan at sunset for Chicago skyline views from the water

Build practical sailing skills aboard a 26-foot Chris-Craft on Lake Michigan

Sail Chicago's lakefront from Museum Row to Navy Pier at sunset

Explore Chicago's past with a private guide and museum admission included

Trace Chicago's skyline story through Loop landmarks

Uncover the women behind Chicago's art, architecture, and civic life