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.
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FEATURED
CRUISE
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2008 SHORELINE SIGHTSEEING TOURS |
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Celebrate summer and the
Labor Day Weekend with Shoreline Sightseeing! Enjoy a Shoreline
Architecture Tour, led by a professional-entertaining docent, viewing
40 famous landmarks. Or, choose a narrated Skyline Boat Tour featuring
the panorama of Chicago’s famous lakefront. Fast, fun water taxis,
too!
Learn More.
Fireworks Cruises Wed. and Sat.
evenings plus special Labor Day Fireworks Cruises Sat, 8/30 and
Sunday, 8/31! Architecture Cruises, Skyline Tours and Water Taxis from
10:00 am daily. |
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"
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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
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 - 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.
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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
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 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
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. |
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'Go Chicago' Card
1 Price-25 Attractions
On Sale 15% Off
Buy Now!
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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.
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ADVENTURE SEA TOURS – CHICAGO SKYLINE CRUISES |
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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. |
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VALARA VI – For
private entertaining in style |

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 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.
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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
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.
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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.
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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.
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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.
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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. |
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THERE'S
STILL TIME TO
CHECK OUT THE SEADOG I, II, IV AND EXTREME! |
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Prepare for the ultimate
speedboat adventure! Cruising at 20-25 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.
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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
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THIS SUMMER ESCAPE FROM
THE ORDINARY ABOARD ODYSSEY |
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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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