things to do in Oak Park, IL

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

Explore Chicago Chinatown on a 2026 USA Today 10Best History Tour winner

Pedal through Chicago neighborhoods while tasting pizza, hot dogs, brownies, and optional beer pairings

Paddle the winding DuPage River past Naperville's quiet corners

Cruise the water with a captain for relaxed outings, playpen visits or evening fireworks

Discover the journey from fresh grapes to wine during Chicago's harvest season

See Chicago landmarks from the water on a private sightseeing outing

Enjoy unlimited rides and more than 50 attractions at a fall farm festival

Create a small custom rug with guided tufting instruction

Private Chicago cruising with a kitchen, bathroom and Bluetooth sound

Work together to conquer fast-paced physical, logic, and skill challenges

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

Build foundational kayaking skills on calm Chicago River waters

Take in Chicago's parks, waterfront, and landmark sights in one ride

Taste Chicago classics and discover the stories behind the city’s signature dishes

Discover Logan Square’s past through handcrafted greystones, historic churches, and ornate storefronts

Captain for hire on Lake Michigan, with payment options and holiday rates

Make your celebration hands-on with cookies and personalized party touches

Photograph Chicago's skyline from a US Navy-built boat

Cruise and swim aboard a spacious Sea Ray with room to lounge

Bring your creativity to the canvas

Charter a private 38' yacht on Lake Michigan for up to 13 guests

A discounted adventure with optional private event space

Private Sea Ray yacht charter on Lake Michigan with 3–8 hour options