Sunset sailing helm silhouette over Lake Michigan skyline

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.

Aerial view of docked sailboats in Chicago marina

Bow deck view toward Chicago skyline during sail

Tours Offered

Three private charters available.

Max Passengers

Private charters for up to six guests.

Boat Type

Downeast

Stylish Downeast powerboat.

ChicaGo By Boat — Private Chicago Boat Charters

Experience Lake Michigan & the Chicago River

ChicaGo By Boat operates private charters in Chicago, Illinois, specializing in small-group boat tours on Lake Michigan and the Chicago River. These private boat charters use a stylish Downeast powerboat and accommodate up to six passengers, making them an excellent choice for intimate sightseeing, corporate outings, and staycations.

What to expect on a ChicaGo By Boat charter

Private, captain-led cruises on Lake Michigan and the Chicago River
Boats designed for comfort and skyline viewing
Capacity for up to six passengers per charter
Guests may bring their own food and pre-mixed cocktails

Popular Private Charters & Event Access

ChicaGo By Boat lists multiple private cruise options, including the Lake Michigan & Chicago River Cruise and Weekday Afternoon Sailing private charters. For special events, ChicaGo By Boat provided viewing access for SAILGP: Rolex United States Sail Grand Prix at Navy Pier on June 16-17, 2023, offering a unique vantage point to watch F50 catamarans race.

Ideal uses for a private charter

Chicago skyline sightseeing and photography
Corporate outings and team-building on the water
Small-group celebrations and social gatherings
Event viewing (for example, Sail Grand Prix at Navy Pier)

Safety & Crew

Each private charter is operated with a licensed captain, ensuring navigation through Chicago waterways and adherence to safety practices. Private, small-group charters reduce crowding and allow for a more personalized experience compared to larger sightseeing boats.

Why choose a private boat charter in Chicago?

Direct access to downtown waterfront views and iconic architecture
Flexibility to plan shorter or longer private cruises
Intimate groups make it easier to socialize, celebrate, or conduct business on the water
A Downeast powerboat combines style and stability for comfortable cruising

Practical details and planning tips

Tours operate from Chicago, Illinois, and focus on Lake Michigan and Chicago River routes.
Charters accommodate up to six passengers; confirm guest count when booking.
Guests are welcome to bring their own food and pre-mixed cocktails; verify any event-specific restrictions in advance.
For special event charters, such as Sail Grand Prix viewing at Navy Pier, confirm date availability and local event regulations.

Keywords for search

This page focuses on high-value search terms related to private Chicago boat charters: Chicago boat tour, Lake Michigan cruise, Chicago River cruise, private boat charter Chicago, Navy Pier viewing, Downeast powerboat, licensed captain charter, private sailing Chicago, SAILGP Chicago.

By emphasizing private, captain-led charters for up to six guests, ChicaGo By Boat targets travelers and locals seeking a personalized, scenic on-water experience in Chicago.

Sailboat cruising with Chicago skyline on Lake Michigan

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.