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 that 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!

Boat tours take you along the Lake Michigan shoreline, where you’ll learn about the different buildings set prominently along the Chicago skyline, or up the Chicago River for a wonderful architectural learning experience. The narrators typically provide interesting information about the history of Chicago and some of its most prominent past citizens. See Our Chicago Cruise Boat Comparison.

Sightseeing Boat Cruises & Tours

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, complimentary 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.

Chicago’s First Lady Cruise

Chicago architecture river tour. The Official River Cruise of the Chicago Architecture Foundation(CAF). Departs Southeast corner of the Michigan Avenue Bridge at Lower Wacker Drive. For reservations call 847-358-1330; groups of 10 or more may call CAF at 312-322-1131.

Entertainment Cruises

at Navy Pier, 600 E. Grand Ave. 866/391-8439

See the world-famous Chicago skyline from the most coveted seat in the city – Lake Michigan. Entertainment Cruises is the nation’s largest entertainment, sightseeing and dining cruise company. With the elegant Odyssey, festive Spirit of Chicago, contemporary Mystic Blue and thrilling Seadog excursions, come aboard for wonderful dining, dancing, entertainment and up-close views of Chicago’s exciting sights – all for one price! With Brunch, Lunch, Dinner, Moonlight, Sightseeing and a variety of specialty cruises year-round, make a remarkable Chicago memory and book your cruise today! Call 866/391-8439 or visit the Entertainment Cruises web site to learn more today.

Lakeshore Sail Charters – Chicago

401 E Monroe Ave, Chicago, IL 60602
708-769-4220

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.

Mercury, Chicago’s Skyline Cruiseline

Departing from Riverside Gardens at Michigan Ave. & Wacker Dr. Chicago Urban Adventure Cruise, May 1 – Oct 1 – 1 1/2 hour River & Lakefront Cruise  $23 adults, $10 children, under 3 free. Bring your own drinks and snacks

Mystic Blue Cruises

at Navy Pier, 600 N. Grand Ave. 877/299-7783

The coolest Chicago experience, come aboard the fresh and contemporary decks of Mystic Blue. We’ve got it all – tasty treats, hot DJ beats, a modern ambiance and the best views of Chicago’s world-famous skyline – all for one great price. With the largest picture windows of any ship at Navy Pier, the 600 passenger vessel was built specifically for cruising the famous Chicago skyline. Mystic Blue Cruises offers Brunch, Lunch, Lake Breeze Dinner Lounge, Fireworks, Blue-After Dark Moonlights and specialty cruises. Departs year-round from Navy Pier. For more information on cruise options and tickets, please call 877.299.7783 or visit the Mystic Blue web site to learn more today.

Odyssey Cruises

at Navy Pier, 600 E. Grand Ave. 866/305-2469

Escape from the ordinary with Chicago’s sleek cruising vessel. Step aboard Odyssey and enjoy a two- or three-hour getaway to the signature elegance and total entertainment experience only a true luxury cruising vessel can provide. Creative appetizers, entrees and desserts are prepared fresh onboard daily. Award-winning wines. Live entertainment. Dancing and unmatched skyline views drift past your table. Offering Brunch, Lunch, Cocktail, Dinner, Fireworks and specialty cruises that are still within reach. Departs year-round from Navy Pier. For more information on cruise options and tickets, please call 866.305.2469 or visit us at the Odyssey web site to learn more today.

Seadog Speedboat Cruises

at Navy Pier, 600 E. Grand Ave. 888/636-7737

One of the most popular attractions at Navy Pier in Chicago, Seadog has thrilled over 1,000,000 people. Seadog offers exciting 75-minute Architectural River & Lake Tours, thrilling 30-minute Lakefront Speedboat Rides and 30-minute Extreme Thrill Rides – a truly wet n’ wild jet-propelled experience! There’s no more amusing, invigorating way to learn about all of the city’s awesome architecture and history than aboard this daring doggie, Seadog! Cruising from Navy Pier April – October, weather permitting. Call 888.636.7737 or visit us at the Seadog web site to learn more today.

Shoreline Sightseeing

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.

Spirit of Chicago

at Navy Pier, 600 E. Grand Ave. 866/273-2469

If you’re looking for a totally entertaining Chicago experience at one great value, look no further than the festive Spirit of Chicago. With a vibrant atmosphere, bountiful buffets, live solo performances, interactive DJs for dancing and amazing up-close views of Chicago’s skyline, splash aboard for a Brunch, Lunch, Cocktail, Dinner, Fireworks or specialty cruise. Perfect for staycations, out of town guests or celebrating any occasion. Cruising year-round from Navy Pier. For more information on cruise options and tickets, please call 866.273.2469 or visit us at the Spirit of Chicago website to learn more today.

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, wedding parties, informal dinner cruises, and fireworks cruises. Did I mention a Pirate themed event? We have a unique venue that your 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,

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

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.