Chicago Cruise Ships

Seadog Speedboats

Many of the Chicago boat tours you'll find below are charming and scenic. You can ride along Lake Michigan on a breathtaking yacht, sail the open seas on a Tall Ship, or take a quick ride on a water taxi. Some travels prefer something a little more adventurous though, and there's no better thrill for an adventure seeker in Chicago than a ride on Seadog Speedboat Tours!

These tours are dog-friendly, kid-approved and come in several varieties!

• The Lakefront Speedboat Tours - Nonstop fun, music and entertainment with fantastic views
• River and Lake Architectural Tour - Everyone loves the beauty of Chicago's architecture and skyline
• Extreme Thrill Ride - For the real adventure seekers!
• Lakefront Fireworks Cruise - Perfect for a summer night or any special occasion.

Shoreline Sightseeing

Architecture Cruise on the Chicago River
Chicago is the birthplace of modern American architecture, and one of the best ways to enjoy the architectural feats that make up the Chicago skyline is on a boat on the Chicago River. Shoreline offers a number of architecture cruises, from the standard sightseeing river cruise to special architecture fireworks cruises or fantastic night architecture tours.
Skyline Tours on Lake Michigan
Shoreline offers many amazing tours on beautiful Lake Michigan, which depart from the Navy Pier - Chicago's #1 tourist attraction. Definitely want to check out Navy Pier, and hop on a Shoreline Skyline Lake Tour by day, at sunset or at night when the fireworks are putting on a show! This is the most memorable way to see Chicago!
Water Taxis
Water Taxis connect many of Chicago's top tourist destinations, so hop on one at the Michigan Ave Bridge, Navy Pier, Museum Campus or Willis (Sears) Tower. These are an awesome way to see the city from the water on a budget!
Walking Tours of Chicago
Not a boat lover? You can still get a great tour of Chicago with Shoreline Sightseeing on one of their walking tours!

Tall Ship Adventures

Tall Ship Adventures is one of our highest rated tours!

Tall Ship Adventures is a fleet of two sailing ships: Tall Ship Windy and Pianissimo. While the Tall Ship Windy is a larger, classic sailing ship, the latter, Pianissimo, is a small, modern ship perfect for private charters of up to 6 people.
The Pianissimo is one of Chicago's most luxurious and newest sailing boat charters, but the owners, your tour guides, are extremely knowledgable, experienced and provide the best possible time.

The Windy offers daily public Chicago boat tours, but can also be chartered for private parties. These are a fabulous idea for team building on a business trip, pirate-themed events or weddings and wedding parties!

Chicago travelers love the personal touch that Tall Ship Adventures offers. Do you want your tour to be a little more hands on? Guests can participate or sail the boat activel, receive instruction and coaching, or just sit back, relax and enjoy!