things to do in Chicago, IL

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

Charter a 47’ Carver yacht with kitchen, bathrooms, and Bluetooth audio

Set the mood on board with your own food, drinks and music

Cruise a 47-foot Carver with space to relax, dine, and play your music

Make your Chicago celebration a private day or night on the water

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

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

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

Choose your paddlecraft for a self-guided outing on the water

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

Explore Chicago River routes by kayak or stand-up paddleboard at your own pace

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

Learn essential sea kayaking skills with certified instructors

Learn paddleboard skills for calm-water adventures

Discover the artists and history behind West Town’s street art

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