things to do in Naperville, IL

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

Private 3-hour sail to view Navy Pier fireworks with a USCG-certified captain included

See Chicago landmarks by helicopter with a 5-passenger twin-engine aircraft

Explore forest preserves on a guided horseback trail ride

Ride countryside trails at sunset, then relax by a hilltop bonfire

Take on a challenging guided trail ride along the Fox River

Ride challenging hills and creek crossings, then gather around a sunset bonfire

Coordinate tactical games across a wooded private battlefield

Ride a foodie bus to restaurants seen in The Bear, with tastings along the way

Taste Mexican cuisine and discover Pilsen’s mural-covered streets

Cruise Chicago’s river in a vintage 1950s Milo Craft

Paddle the Chicago River after dark with city lights and stories from your guide

Paddle Lake Michigan’s shoreline for city views and guided instruction

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

Paddle past the Wild Mile and Chicago's skyline in a single or double kayak

Paddle the Chicago River in a single or double kayak, from the Wild Mile toward downtown

Build foundational kayaking skills on calm Chicago River waters

Explore the Old Joliet Prison's history, inmate stories, and surviving cell blocks

Walk through Chicago scenes from Ferris Bueller, The Dark Knight, and more

Follow Chicago’s movie trail with a local actor guide

Explore interactive exhibits and artifacts from Joliet’s past with access to galleries for all ages