Chicago Boat Tours Comparison Lakefront and River

Sailing on Lake Michigan

Sailing and Sailboat Tours in Chicago IL

Chicago Interactive Map


Odyssey Chicago IL

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 day and evening departures of its award-winning Architecture River Tours as well as special Architecture Fireworks Tours, Memorial Day to Labor Day, from two locations: Navy Pier and the Michigan Avenue Bridge.
Classic Lake Tours
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 Classic Lake Tour by day, at sunset or at night including special Lake Fireworks Tours 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!

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!


Chicago Travel Info
  Venue Info Price
Chicago Private Yacht Rentals
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Adult Price

Architecture River Tour
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Classic Lake Tour
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Adult Price

Shoreline Sightseeing
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Adult Price

Adventure Sea Tours
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Adult Price

Chicago Line Cruises
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Architecture Foundation Tours
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Anita Dee Yacht Charters
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Adult Price

Odyssey Chicago Cruises
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Adult Price

Tall Ship Adventures
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Adult Price


One of the best way to see Chicago is by way of boat, and when you take one of the Chicago boat tours, you get all the best views, history, information and food the city has to offer! All of the boat tours in Chicago have so much to offer, so the hardest part is choosing the one that's right for you! This page provides a brief comparison of various Chicago boat tours and cruises which are available to Chicago Travelers. Get out of the hotel in Chicago and see everything that this beautiful city has to offer you! If you feel like you can't afford to see all these great things (yeah, the Windy City can get pretty pricey) think again! There are lots of great deals on things to do in Chicago, and even Chicago hotel deals that can save you big so you can see even more of the city while you're here!

Links are provided to allow you to confirm cruise details regarding boat departure times, credit card acceptance, menus, etc. You can also view more choices and descriptions of selected cruises by visiting the Chicago Sightseeing Cruises, Tours & Private Charters or Chicago Fireworks Cruises pages. All information is subject to change.  Be sure to check with the Cruise Company to verify cruise types, pricing and hours/dates of operation.  Price ranges typically indicate differences pertaining to day of week.  Prices generally do not include taxes, fees, or gratuity. Some cruises are summer only, and in general cruise schedules are limited in the cold months.

Chicago boat tours comparison or lakefront and river tours:

INDIVIDUAL AND GROUP Chicago boat tour comparison list:

Odyssey Cruises

  • Navy Pier
  • Chicago boat tours Lakefront & Dining
  • Year-Round
  • 2-3 Hours
  • Plated Dinner, Plated Lunch, Buffet Brunch
  • Upscale DJ, Moonlight Cruises, Charters, Fireworks Cruises
  • $44-$130
  • Alcohol Served
  • Private Parties and Charter Tours Available

Seadog Cruises

  • Navy Pier
  • Lakefront Sightseeing, Architectural Tours
  • April-October
  • 30-75 mins
  • Charter Options Available, Fireworks Cruises
  • $19-$36
  • Alcohol permitted if puchased at Navy Pier

Shoreline Sightseeing

  • Navy Pier
  • Michigan Avenue Bridge
  • Lakefront Sightseeing, River Architectural
  • April-November
  • 40-75 mins
  • Concessions
  • Fireworks Cruises
  • $25-$43

Shoreline Water Taxi

  • Various Locations
  • Water Taxis
  • May-September
  • $3-$10

Spirit of Chicago

  • Navy Pier
  • Chicago boat tours Lakefront, Dining
  • Year-Round
  • 2-3 Hours
  • Buffet Dinner, Buffet Lunch
  • Interactive MC Passenger, Cabaret Lunch, Gospel Lunch, History Lunch, Charters, Fireworks Cruises
  • $39-$100
  • Private Parties and Charter Tours Available

Anita Dee Yacht Charters

  • Navy Pier
  • Chicago boat tours Lakefront
  • April-October
  • 45 mins
  • Concessions
  • Fireworks Cruises
  • $15-$25

Mystic Blue Cruises

  • Navy Pier
  • Chicago boat tours Lakefront
  • Private parties and charter tours
  • Breakfast, lunch and dinner tours available
  • Alcohol served
  • $36.90- 88.90 per passenger

Adventure Sea Tours - Luxury Yacht Valara VI

  • Burnham Harbor
  • Private event yacht
  • Chicago yacht tours Lakefront
  • Various times and packages available
  • Dinner and alcohol served
  • $43- $126 per person

Mercury Cruiseline

  • Riverside Gardens
  • Urban Adventure, Wacky Pirate Cruise, Canine Cruise, Lakefront Fireworks, Sunset Cruise, Supernatural Cruise
  • May-September
  • 60-120 mins
  • BYO Drinks/Lunch
  • River and Lakefront Cruises
  • $23-$28

Chicago Line Cruises

  • North Pier/River East Plaza
  • Chicago River boat tour Architectural
  • April-October
  • 90 mins
  • Coffee, Soft Drinks & Cookie included
  • Historical Cruise
  • $36

Wendella Boats

  • Michigan Ave
  • Chicago boat tours Lakefront, Chicago River boat tour Architectural
  • April-November
  • 1-2 Hours
  • Concessions
  • Sunset Cruise, Fireworks Cruise
  • $22-$25

PRIVATE CRUISE CHARTERS Chicago boat tours comparison of lakefront and river tours:

Go Sailing Chicago

  • Private Charter for 6
  • 3 Hour min
  • $150-$225 per hour
  • BYO refreshments/snacks

Kanan Cruises, Inc.

  • Private Charters for 50-400 persons
  • 2-4 Hours
  • $44-$98 per person
  • Live DJ, Soda/Juice Service, Open Bar, Live Music, Live Pianist, Hors D'oeuvres, Snack Buffet, Lunch/ Dinner Buffet

Cruise Chicago

  • Private Charters up to 200 guests
  • 2 Hour min
  • $775-$1,275 per hour
  • Customized Catering & Bar Packages, Live DJ or Live Band, Custom Décor ~ Accommodate private charters of all kinds

Sophisticated Lady

  • Private Charters up to 49 guests
  • 3 Hour min
  • From $108 per person
  • Various theme or custom menus

ATTENTION TOUR BOAT OPERATORS: Send us your updated tour information so that we can provide your current boat details for the current season. Send the specific changes to us at support (at) Thanks.