Chicago Sightseeing Boat Cruises-Tours & Charters

Try one of the many leisure boats docked along Navy Pier's Dock Street, the River or Burnham Harbor for a unique Chicago lakefront experience you won't soon forget. There are a variety of boat choices which offer you everything from fancy dinner cruises that include dancing and live entertainment to exciting speedboat rides along Lake Michigan and water taxi rides between lakefront attractions. From the luxury to the budget, there is a fun boat for every occasion along Chicago's Lake Michigan! 

Sightseeing Boat Cruises | Private Cruise Charters

*** See our Chicago Boat Tours Comparisons before you book a boat tour. ***

FEATURED CRUISE

2008 SHORELINE SIGHTSEEING TOURS

Shoreline Skyline Lake Tour on Lake Michigan

Shoreline Sightseeing’s summer season is in full swing! Join Shoreline’s professional-entertaining docents on a fascinating Chicago River Architecture Cruise viewing 40 famous landmarks. Or, choose a narrated Skyline Tour featuring the entire panorama of Chicago’s famous lakefront & skyline. Learn More. Plus daily Sunset Cruises and Fireworks Cruises Wed. and Sat. evenings plus holidays! Architecture Cruises and Skyline Tours from 10:00 am daily. Fast, fun Water Taxis, too! Click Here.

Sightseeing Boat Cruises & Tours

*** See our Chicago Boat Tours Comparisons before you book a boat tour. ***

Chicago Architecture Foundation-Chicago River Cruise
This 90-minute cruise highlights 53 historic and architecturally significant sites including: the Trump Tower, Merchandise Mart, 333 W. Wacker, the Wrigley Building, the Tribune Tower, the Sears Tower, River City, Marina City and the site of the Spire. Offered aboard Chicago's First Lady Cruises, it is led by trained volunteer docents. Cruises depart from the lower level/southeast corner of the Michigan Ave Bridge at Wacker Dr. Individual tickets are available by phone at 312-902-1500, or online. Snacks/beverages may be purchased.
Chicago Line Cruises 465 N. McClurg Ct. St. Chicago 312-527-2002,
Chicago Line Cruises offers public architectural and historical cruise by boat from their exclusive dock at historic North Pier/River East Plaza. Each cruise is a 90-minute narrated tour by a professional docent, complementary Starbucks coffee, lemonade, and cookies. The architectural cruise covers both the north and south branches of the Chicago River and the historical cruise travels out on Lake Michigan and on the Chicago River. Email to info@chicagoline.com
Chicago Greeter "Free Tours"
Chicago's First Lady   Chicago architecture river tour. Departs Michigan Ave/ Lower Wacker Drive. 847-358-1330 charters; 312-902-1500 tour reservations
Entertainment Cruises-Chicago
Entertainment Cruises
Give your group a fresh perspective on one of the most spectacular views in America-the Chicago Skyline. No matter what you demand of your venue, count on Entertainment Cruises to deliver it, effortlessly. We are the nation’s largest entertainment, sightseeing and dining cruise company. With six unique brands cruising in eight cities, we provide the most memorable alternatives to land based attractions. Great service. Spectacular views. Flawless execution. Plan your next Chicago outing with Entertainment Cruises, a company dedicated to exceptional high value, high entertainment experiences. For groups of 20-2000, we can create an event for any budget. 866/391-8439
Lakeshore Sail Charters
Lakeshore Sail Charters - Chicago
401 E Monroe Ave, Chicago, IL 60602
708-769-4220 chicagoevent@lakeshoresail.com
At Lakeshore Sail Charters in Chicago, we offer a unique, personalized, owner-operated sail charter experience on our new boat. We have affordable rates with hourly, daily and custom packages.
mystic blue cruises at chicago's navy pier
Mystic Blue Cruises
at Navy Pier, 600 N. Grand Ave. 888/330-4700
The newest dinner cruise ship at Navy Pier, Mystic Blue Cruises will incorporate everything you love about Duck Cruises, a fun and casual atmosphere with great food and incredible service, but almost every aspect of the experience - from our menu to our colors to our carpet, tables, and chairs - will be upgraded to make yours the finest contemporary and casual event on the water. With the largest picture windows of any ship at Navy Pier, the newly remodeled sleek, silvery-blue, 500 passenger vessel was built specifically for cruising the famous Chicago skyline. Mystic Blue Cruises offers lunch, midday, dinner, and moonlight cruises, year ’round. 
odyssey lakefront cruises at chicago's navy pier
Odyssey Cruises Escape from the ordinary. Step aboard Odyssey and enjoy a two- or three-hour escape to the signature elegance and total entertainment experience only a true luxury cruising vessel can provide. Creative appetizers, entrees and desserts prepared fresh onboard daily. Award-winning wines. Dancing to live music. And unmatched skyline views drifting past your table.h, dinner and midnight cruises. Departs Navy Pier, 600 E. Grand Ave. 888-957-2328
seadog cruises at chicago's navy pier
Seadog Speedboat Cruises

One of the most popular attractions at Navy Pier in Chicago, Seadog has thrilled over 1,000,000 people. Offers both Speedboat Lake Tour as well as a River & Lake Architecture Tour.

Shoreline Sightseeing/Architecture Cruises/Charters/Water Taxis
One hour Architecture Cruises from Navy Pier on the historic Chicago River viewing over 40 famous buildings. Professional docents recount the dramatic story of Chicago’s rise from the ashes of the Great Fire of 1871 to become the birthplace of the skyscraper and the home of modern American architecture. Free souvenir map/guide. Skyline Boat Tours from Navy Pier offer half-hour Lake Michigan tours with professional narration on Chicago’s colorful history and world-renowned skyline. Fast Fun Water Taxis run between Sears Tower, Michigan Avenue Bridge, Navy Pier and the Shedd Aquarium/Museum Campus. Special Fireworks Cruises and Theme Cruises throughout the season. For more information please call 312-222-9328 or visit us online. Buy tickets in advance online or by phone for special savings.

See the Shoreline Water Taxi Video | Review of Architecture River Cruise

Spirit of Chicago Cruises
Spirit of Chicago Step aboard the Spirit of Chicago cruise at Navy Pier for an afternoon or evening of unparalleled cruising fun on the lakefront in Chicago. Enjoy this luxurious Chicago cruise ship while you dine, dance, enjoy star-quality entertainers and breathtaking skyline views, all for one price. For two, ten, or 600 guests, a Spirit of Chicago cruise will blow you away.
Tall Ship Red Witch, Chicago's Schooner
Where: Burnham Harbor, in Museum Campus near Soldiers Field
Phone: 312-404-5800,
Avast, the Red Witch is a traditional (wood) topsail schooner. This Tall Ship is available in Chicago for private charter or ticketed events (call or check web site for availability), for up to 49 passengers. Ideally suited for summer corporate events, special occasion parties, weddings parties, informal dinner cruises, and fireworks cruises. Did I mention a Pirate themed event? We have a unique venue that you guests will remember! Heed that call to do something different! You can check availability and make your reservations online or just call us for details!
Wendella Boats
400 N. Michigan Avenue
312- 337-1446, email: tours@wendellaboats.com
As a family run business in its fourth generation, Wendella has evolved into Chicago's most comprehensive boat tour. Wendella's in-house education department is the first of its kind in the industry. Our experienced and knowledgeable docents and tour guides provide educational and insightful narration about Chicago, it's rich history and magnificent architecture. From the Chicago River Architecture Tour, our signature Combined Lake and River Tour, or Chicago At Sunset, Wendella is perfect for families visiting Chicago or groups on an outing.
Windy City Sailing
Belmont Harbor
773-868-0096, email: info@windycitysailing.com
Windy City Sailing, Inc. offers World-Class recreational, romantic and educational experiences to individuals and small groups. Experience the thrill of sailing, with professional captains on our custom sailing yachts, including the luxury, 39-foot, 2004 Beneteau.

The 'Go Chicago' Card - 25 Attractions for One Low Price!
 'Go Chicago' Card
1 Price-25 Attractions
On Sale 10-15% Off
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*** See our Chicago Boat Tours Comparisons before you book a boat tour. ***


Chicago Private Cruise Charters (no individual reservations)
Listings below for private cruise charters not for individual/group reservations.


ADVENTURE SEA TOURS – CHICAGO SKYLINE CRUISES

Adventure Sea Tours- Valara VI Cruises

PRIVATE ENTERTAINING SKYLINE CRUISES.
For those who care about quality during their entertaining experience, Valara VI is a full-service luxury yacht serving Chicago’s most special occasions. Serving only one group at a time up to 149 guests with unmatched class. Get away from the old way of entertaining on land, to an atmosphere that will set your experience apart from the rest. In business over 35 years. Visit our website, or call 773-788-9494.

VALARA VI – For private entertaining in style


Adventure Sea Tours- Valara VI - Charters
Adventure Sea Tours, Inc.
Burnham Harbor - Chicago, IL 773-788-9494, email: valara006@comcast.net 
Featuring the Luxury Yacht Valara VI with an unmatched atmosphere that is conducive to the mingling of your invited guests and viewing of our Chicago Skyline in ultimate style and comfort. Full-service luxury yacht for your private Corporate Entertaining, Weddings and Fine Family Gatherings. Serving group sizes up to 149 Guests. Valara VI sets your entertaining experience apart from the rest.
Private Cruises only. In business over 35 years.
Anita Dee Yacht Charters
Navy Pier, Chicago
312-379-3191, email: info@anitadee.com
Make Chicago Yours Exclusively! Located at Navy Pier, Anita Dee Yacht Charters specializes in private cruises for groups of 50-400. Choose your date, time and direction of sailing aboard one of two luxurious vessels. If you would like additional information please contact us at 312-379-3191 or online at www.anitadee.com.
Charter Boat Chicago
111 N. Lake Shore Dr.
(312) 213-BOAT (2628)
email: info@CharterBoatChicago.com
Premier sport fishing and private boat excursions in DOWNTOWN CHICAGO! - fishing with a view - sunset & skyline cruises - fireworks - Chicago river tours - or just relax aboard a BEAUTIFUL 36 foot Egg Harbor Yacht.
Chicago Cruises
Chicago Cruise's "Summer of George"
Docked at State Street & the Chicago River.
Chicago Cruises offers customized corporate outings & private party cruises, as well as daily Sunset Cruises. Call 866.213.5568 or visit web site for pricing and availability. Email: info@chicagocruises.com.
Chicago Sailboat Charters
Belmont Harbor
773-960-7890
Come for a sail with us on the Chicago shoreline. Day or night, we provide a great experience for first timer sailors or enthusiasts. Fireworks, sunsets, sunny days, even sunrises! Our goal is to tailor your sailing experience specifically to you.
773-960-7890
El Presidente Yacht Charters
Navy Pier
312-595-0059, email: info@el-presidente.com
Luxury yacht available for up to 60 guests
Entertainment Cruises-Chicago
Entertainment Cruises
Give your group a fresh perspective on one of the most spectacular views in America-the Chicago Skyline. No matter what you demand of your venue, count on Entertainment Cruises to deliver it, effortlessly. We are the nation’s largest entertainment, sightseeing and dining cruise company. With six unique brands cruising in eight cities, we provide the most memorable alternatives to land based attractions. Great service. Spectacular views. Flawless execution. Plan your next Chicago outing with Entertainment Cruises, a company dedicated to exceptional high value, high entertainment experiences. For groups of 20-2000, we can create an event for any budget. 866/391-8439
Free Spirit Yacht Cruises
Burnham Harbor, Chicago, Ill 708-361-2220, info@freespiritcruises.com
The "Gypsy Spirit" and the "Free Spirit" are two luxurious yachts that are offered for charter, accommodating up to 120 people.
Lakeshore Sail Charters
Lakeshore Sail Charters - Chicago
Location: Burnham Harbor, in Museum Campus, near Soldier Field
Phone: 312-404-5800
At Lakeshore Sail Charters in Chicago, we offer a unique, personalized, sail charter experience on our fleet of sail boats. The fleet ranges from 33 foot to our flagship Red Witch, which is 77 feet long!! We have affordable rates with hourly, daily and custom charter packages. Take a look at our web site for more details. We also have an online reservation system where you can check the availably and make your sailing reservations. Or… just call us, you will almost always be answered by a friendly voice. Advance reservations are not required.
Second City Cruises
630-788-9202, email: forddad2003@yahoo.com
Private charters (Captain included) along the Chicago Shoreline or on the Chicago River on our spacious 27' Sea Ray. Charter the whole boat for your group of 1 to 6 people. We offer Chicago River tours, fireworks cruises, romantic night cruises along the Chicago skyline. You can even cruise off Northerly Island during Charter One Pavilion concerts. 
Set Sail Chicago
77 West Washington Suite 1801 Chicago IL 60602
877-578-SAIL, email: info@setsailchicago.com
Set Sail Chicago is Chicago's premier corporate and recreational sailing charter company.
Showcasing the beauty and atmosphere of Chicago city sailing, our luxury sailboats and accommodating crews provide guests an intimate and personalized boating experience.

Set Sail Chicago offers recreational cruises, sailing lessons, corporate entertainment and interactive team building events. Our charters are a great way to entertain clients, celebrate team success or just to relax and enjoy a day or evening out on the waterway.
Shoreline Charters
Private charters are available for 50 to 240 guests on a choice of four vessels including the four-season Celebration. Cruise on Lake Michigan and/or the Chicago River. Architectural docents are available on request. Ideal for social and corporate events day or evening, casual to elegant themes. Shoreline's professional event planning staff will handle every detail. Please call 312-222-9328, ex 2232, or visit the Shoreline web site www.shorelinesightseeing.com. See the Shoreline Water Taxi Video.
A Sophisticated Lady Yacht Charters
Burnham Harbor, Chicago, IL 60605
773-224-2783, fantasy1@flash.net
A Sophisticated Lady Yacht Charters is a private luxury yacht in Chicago for 10 - 49 passengers specializing in corporate and personal events. Pricing starts at $65 per person including food and beverages.
SunSea Yacht Charters
Chicago's Lakefront - Burnham Harbor
773-284-4782, email: info@yachtparties.com
Beautiful private charter yacht offering cruises on Lake Michigan. Home-like setting for your next party, wedding, or special event.
Tall Ship Red Witch, Chicago's Schooner
Chicago, Museum campus
312-404-5800, email: chicagotravelerRW@lakeshoresail.com
The topsail schooner Red Witch is available in Chicago for hourly charter or ticketed events (call or check web site for availability), for up to 49 passengers.
Ideally suited for day sails, corporate events, special occasion parties, weddings, informal dinner cruises, sales incentives, and fireworks cruises.
Windy City Sailing
Belmont Harbor
773-868-0096, email: info@windycitysailing.com
Windy City Sailing, Inc. offers World-Class recreational, romantic and educational experiences to individuals and small groups. Experience the thrill of sailing, with professional captains on our custom sailing yachts, including the luxury, 39-foot, 2004 Beneteau.

THIS SUMMER CHECK OUT THE SEADOG I, II, IV AND EXTREME

Chicago Seadog Summer Cruises on I, II, IV and Extreme

Prepare for the ultimate speedboat adventure! Cruising at20-25 knots, the 70-foot long Seadog Vessels offer fun and excitement for guests of all ages! The Seadog I, II, & IV, are three of the fastest speedboats in the country. Now cruise into a truly wet and wild experience with the Seadog Extreme,  30% faster than her doggie siblings,  Learn More.

 

Selected Sightseeing Cruises Boat Descriptions

Windy
WINDY is Navy Pier's resident 148-foot, four-masted schooner. She offers 90-minute public cruises, private charters and educational trips, are offered each day. The ship pays tribute to the Great Lakes' rich maritime heritage by featuring a design reminiscent of a traditional American schooner. WINDY holds up to 150 passengers per cruise and visiting landlubbers are encouraged to help raise and trim her 11 sails and often take turns at the ship's wheel. Cruises are available daytime and evenings from May to October. For more information about Windy, please call (312) 595-5555.

Seadog I, II, III and IV
Hold on to your hats! Cruising between 20 and 25 knots, the 70-foot-long Seadog vessels offer fun and excitement for guests of all ages. The Seadogs are four of the fastest speedboats in the country. Departing continuously each day (May through October) from the Pier's Dock Street, each Seadog adventure lasts 30 minutes, cruising the lakefront with 15 feet of cool spray shooting from their sterns. 75-minute architectural tours are also available. For more information about the Seadogs, please call (312) 822-7200 or visit their website at http://www.seadogcruises.com

Shoreline Sightseeing/Water Taxis/Architecture Cruises/Charters

Offering 30-minute skyline tours from the west end of Navy Pier, Shoreline Sightseeing boats are the perfect way for the entire family to experience the majesty of Chicago's lakefront. Shoreline Sightseeing also offers water taxis on two routes: between the southwest corner of Navy Pier and the Museum Campus or the Sears Tower. Shoreline's popular one-hour architecture cruises depart from Ogden Slip at Navy Pier and travel the Chicago River viewing over 40 masterpieces of modern architecture. All cruises are led by architectural guides. Passengers receive a complimentary map and guide outlining the famous buildings along the route. Shoreline also offers private event charters on four vessels, including "Star of Chicago" and the brand new "Evening Star". Professional event planning staff available to assist with charter arrangements. For more information, including exact schedules, please call (312) 222-9328 or visit the Shoreline website at www.shorelinesightseeing.com.

Dinner Cruises

Spirit of Chicago

The Spirit of Chicago offers the liveliest parties on Lake Michigan with lunch, brunch or dinner sightseeing cruises. Cruises on the Spirit of Chicago include a skyline narration during lunch cruises and live cabaret style entertainment on dinner cruises, performed by talented Spirit entertainers. With a capacity of 600 passengers, the Spirit of Chicago sails year-round and is available for group charter or individual reservations. For more information on cruise options and tickets, please call (312) 836-7899 or visit the website at www.SpiritofChicago.com.

The Odyssey

Step aboard the Odyssey for elegant surroundings, fine dining and exceptional live entertainment. With three climate-controlled decks, cruise the lakefront in comfort year-round. The Odyssey accommodates up to 750 guests. For more information on cruise options and tickets, please call (800) 947-9367 or visit the website at http://www.odysseycruises.com

Mystic Blue Cruises

Navy Pier's newest cruise ship offers lunch, Midday, dinner and midnight cruises depart daily, featuring entertaining DJs, dancing and humorous buffets. Mystic Blue Cruises can accommodate up to 600 passengers. For more information on cruise options and tickets, please call (888) 330-4700 or visit the website at http://www.mysticbluecruises.com.

Private Charters

Anita Dee I & II

The Anita Dee pampers its guests all year long, offering all the amenities of premier hospitality passenger boats and specializing in personal service. The Anita Dee I holds 50 to 149 passengers; the Anita Dee II is available for larger groups up to 400. Cruises can be customized for special parties or groups. For more information, please call 312-379-3191 or visit the website at www.anitadee.com.

El Presidente

During her years of government service, the El Presidente was used by US presidents, foreign dignitaries and heads of state for meetings and other official functions. She is docked at Ogden slip, just west of Navy Pier. The recently restored yacht offers her guests luxurious surroundings, including original Art Deco style furnishings, a teak afterdeck and companionways, and an elegantly appointed main salon trimmed in teak and mahogany. This historic cruising yacht can be chartered by the hour, day, week or month. For more information, please call (312) 595-0059 or visit the website at www.el-presidente.com.

Eleanor R.

Originally built as a whale-watching boat, this 90-foot-long vessel boasts wide side decks and a spacious upper deck ideal for viewing Chicago's magnificent skyline. Guests are protected from the elements in a 50-foot main salon and a partially enclosed upper deck. The Eleanor R is available for private charter. For more information, please call (312) 595-0059 or visit the website at www.el-presidente.com.

Visit the Picton Castle's website, a tall ship that was at Navy Pier's AT&T Tall Ships Chicago event over Labor Day weekend 2000. Their website is www.picton-castle.com

THIS SUMMER ESCAPE FROM THE ORDINARY ABOARD ODYSSEY

Chicago Odyssey Escape from the Ordinary Cruises on Lake Michigan

Step aboard Odyssey and enjoy a two- or three-hour escape to the signature elegance and total entertainment experience only a true luxury cruising vessel can provide. Creative appetizers, entrees and desserts prepared fresh onboard daily. Award-winning wines. Dancing to live music. Unmatched skyline views drifting past your table. Enjoy fireworks dinner cruises Wed. & Sat. nights this summer. Learn More.

 


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