Private Chicago Boat Charters on Lake Michigan & the Chicago River
Stylish Downeast powerboat charters for up to six guests — licensed captain, BYO food and cocktails, sail past Navy Pier and the city skyline.
Featured Trips & Private Charters
Small-group private cruises tailored for sightseeing, corporate outings, and special events on Lake Michigan and the Chicago River.
About ChicaGo By Boat
ChicaGo By Boat is a Chicago-based private charter operator offering small-group cruises on Lake Michigan and the Chicago River. The company runs stylish Downeast powerboats designed for intimate groups, accommodating up to six passengers per trip. Each charter is crewed by a licensed captain who navigates Chicago’s waterways and provides a safe, scenic experience for sightseeing and social outings.
Trips include private Lake Michigan and Chicago River cruises ideal for city skyline views and relaxed time on the water. Weekday Afternoon Sailing charters are available for corporate outings or personal staycations, with the same six-passenger private capacity. For special events, ChicaGo By Boat provided access to premium vantage points for the Rolex United States Sail Grand Prix in Chicago, held at Navy Pier on June 16-17, 2023, allowing guests to watch high-speed F50 catamarans race against the skyline.
Guests are invited to bring their own food and pre-mixed cocktails aboard each private charter. ChicaGo By Boat emphasizes a personalized on-water experience, focusing on safety, local knowledge, and flexibility for small groups. Operating from Chicago, Illinois, the company concentrates on private, licensed, captain-led charters for visitors and residents seeking a curated waterfront experience without large-group crowds.
Tours Offered
3
Three private charters available.
Max Passengers
6
Private charters for up to six guests.
Boat Type
Downeast
Stylish Downeast powerboat.
Book a Private Chicago Boat Charter Today
Reserve a Downeast powerboat for up to six guests — licensed captain, BYO food and cocktails, ideal for skyline sightseeing and special events.