Table Of Content
- City Cruises – Premier Dinner Cruise on Lake Michigan
- Tips for a Successful Sunset Chicago Architecture Boat Tour
- The Wharf Welcomes Its First True Barbecue Spot
- Best Sunset Chicago Architecture Boat Tour – Prices and What to Expect
- The Official Flagship of the City of Chicago
- City Cruises – Odyssey Lake Michigan Brunch Cruise
- Cruise & Tour Types

And a fancy sailboat manned by a fine-dining chef pairs tasting menus with French wines. Catch the Chicago skyline at sunset during the most beautiful time of the year, and join us for a fun, laid-back, 2-hour cruise. Spirit’s Lakefront Breeze Dinner Cruise is the perfect way to kick back, relax and take in the best of the city.
City Cruises – Premier Dinner Cruise on Lake Michigan
Vacatis operates the website to provide the most accurate and up-to-day information for tourists and locals. You can have complimentary refreshments such as coffee from Starbucks, bottled water, and sodas on the cruise. Advance reservations are recommended as many tours sell out.
Tips for a Successful Sunset Chicago Architecture Boat Tour
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The Wharf Welcomes Its First True Barbecue Spot
Highly recommend the 7pm sail to watch the sunset between the buildings. Fun and knowledgeable crew made the Windy the highlight of our Chicago visit. For the best Chicago sunset, visitors and residents alike, join us aboard the 148′ Tall Ship Windy – the official ambassador for the City of Chicago.

Best Sunset Chicago Architecture Boat Tour – Prices and What to Expect
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The Cruise will navigate from the Chicago River, through the Chicago Lock and out onto Lake Michigan. Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise. I’m a life long Chicagoan and I brought my out of town relatives on this cruise and we all loved it! It was a gorgeous summer late afternoon and the city was just sparkling. I thought the price was great for the experience.
We highly recommend this tour for architecture enthusiasts and history buffs! You will learn about Art-deco, Gothic, and Neoclassical architecture styles. You are accompanied by a well-informed tour guide who provides detailed information on the architectural history of Chicago and its famous architects. Chicago's Leading Lady, Chicago’s Classic Lady, and Chicago's Emerald Lady are wheelchair-accessible. These vessels cruise at the 9am, 10am, 11am, 12pm, 1pm, 2pm, 3pm and 5pm departure times.
City Cruises – Odyssey Lake Michigan Brunch Cruise
Odyssey Lake Michigan presents special prix fixe dinner cruises, offering guests the opportunity to try one of Chicago’s most unique dining experiences at an incredible... When you dine on Like Michigan, every table is the best in the house. Navy Pier’s brunch, lunch and dinner cruises pair world-class cuisine with panoramic views of the city and lakefront. The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats.
Choose Tall Ship Windy For Your Special Event
There is something special about sailing in Chicago combined by kicking off your week and joining us for a 2-hour concert sail. This Navy Pier boat tour sails from 7pm-9pm every Monday this summer. Most architecture boat tours last for around 1.5 hours. The most baller option of the bunch by far, the Wharf’s luxe Pendry hotel offers guests a captain-chartered Aviara cruise that’s available to the public for the first time. Bar selections, beer or wine, and appetizers can be customized, depending on the parties’ preference.
Cruise & Tour Types
On these 30-minute speed boat rides, you’ll tear across Lake Michigan at up to 45 miles per hour while getting entertaining and informative commentary on Chicago. Sea Suite Cruises’ fleet that started it all is a pontoon pedal boat outfitted with 10 cycle stations (or just let the motor power the party). BYOB (just no hard liquor) or purchase on-board beverages like canned Cutwater ($4-$8.50).
Very friendly and funny staff and always a good time, with beautiful views of the city of Chicago. I've set sail on Tall Ship Windy 4-5 times over the past few years, and it is always a good time. You get a nice view of the city and the crew is entertaining and knowledgeable. Tall Ship Windy offers an unforgettable sailing experience. Explore Chicago’s Skyline and choose from Sunset Sails, Skyline Sails and Educational Sails. Host a truly unforgettable event on Lake Michigan.
It’s the perfect way to end your workday or kick off your weekend plans. History comes alive on this exciting Windy City boat tour. Enjoy an educational adventure for curious minds of all ages with the backdrop of the iconic Chicago skyline always in view. Led by our crew-educators, experience a hands-on sailing excursion in Chicago aboard Windy. We are the only tour that partners with the Chicago Architecture Center to offer the official Chicago Architecture Center River Cruise aboard Chicago's First Lady.
Savor the views with friends and family as you enjoy a relaxing evening on the water with cocktail in-hand. Docks are home to a surge of drinking vessels designed for every occasion, vibe, and price point. A returning line of retro motor boats are apparently the ticket to getting engaged, with seven proposals out on the water last year. Want to watch dolphins give birth on the Chesapeake this summer?
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