things to do in Oak Park, IL

Ride a Yamaha VX WaveRunner across Lake Michigan with Chicago skyline views

Ride a Yamaha jet ski across Lake Michigan with views of Chicago's skyline

Cruise the Chicago River for 2 hours on a private, self-drive pontoon

Cruise Lake Michigan on a historic fireboat for Navy Pier fireworks views

Night kayak tour to watch Navy Pier fireworks

Learn About Winemaking in the Heart of Chicago

Take the wheel on a 22 ft pontoon cruise on the Chicago River

Paddle Lake Michigan with Chicago skyline views

Paddle Chicago's lakefront with skyline views and basic instruction

See Chicago fireworks from a floating tiki bar on Lake Michigan

Watch Chicago fireworks on a 90-minute tiki bar cruise

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

Stretch, cuddle and take photos with rescue puppies in a private yoga session

Eat your way through Uptown’s immigrant neighborhoods in 2.5 hours

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

Taste Lincoln Square’s European roots and Silk Road flavors on foot

Bike and taste your way through Miami Beach’s Art Deco streets and local eats

See holiday lights, market traditions, and Chicago's tree on a downtown stroll

Taste Chicago's holiday flavors and festive sights on foot

Cruise Chicago waters with up to 13 guests for a flexible three-to-four-hour outing

Explore Lake Michigan by boat, from Playpen outings to Chicago river cruises

Bring your group aboard for a captain-led Chicago outing

Cruise Chicago’s waterfront with a certified EMT captain

Cruise Chicago with a flexible captain for your 3–4 hour charter