Best 321 things to do in Naperville, IL

Taste Vietnam, the Middle East, and Sweden while exploring Argyle and Andersonville with a guide

Ride Lake Michigan with downtown Chicago views

Jet ski on Lake Michigan with skyline and Navy Pier views

Private 6–8 hour fishing charter for up to 6 on Lake Michigan

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

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

Help open the barn with hands-on farm animal care

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

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

Coordinate tactical games across a wooded private battlefield

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

Take on a challenging guided trail ride along the Fox River

Host a private kitten yoga party with playtime at The Arboretum of South Barrington