things to do in Oak Park, IL

Take home six cupcakes decorated by you

Rent a bike by Chicago’s Lakefront Trail with maps, helmet, lock, and easy access near Navy Pier

Hire a captain for 3–4 hours, with flexible languages and a safety-first focus

Celebrate on a tiki-themed yacht with an open bar and Chicago skyline views

Rent a bike for 24 hours near the Lakefront Trail and Navy Pier

Cruise on a 46 ft Sea Ray Express with up to 13 guests

Feel the raw power of a 707-horsepower American muscle sedan

Rent a bike near the Lakefront Trail and Navy Pier—return it by shop closing

Cruise Chicago by private boat on a 50 ft Sea Ray Sundancer, up to 13 guests

Cruise the Chicago River aboard a private floating tiki bar

Cruise Chicago on a 10-mile Lamborghini Urus ride

Rent a bike for 4 hours steps from Navy Pier and the Lakefront Trail

Hire a Lake Michigan captain familiar with Chicago’s boating hot spots

Paddle Lake Michigan for Chicago skyline views

Private Chicago river and lake charter with an included open bar

Float through Chicago’s skyline on a festive fall hayride

Host a private celebration aboard a Hamptons-inspired catamaran

Spend a relaxed day on Lake Michigan with a licensed captain at the helm

Feel Porsche handling in an all-wheel-drive electric sedan

See Chicago landmarks from the back seat of a Rolls-Royce with a private driver

Celebrate, cruise, and swim aboard a 52-foot Sea Ray

Cruise Chicago with a safety-focused captain experienced in commercial fishing

Twin-turbo V8 performance with grand-touring comfort

Drive a seven-passenger performance SUV with leather, wood, and all-wheel drive