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Compare boat and sailing experiences by itinerary, duration and departure arrangements. Read the individual inclusions to distinguish sightseeing trips from experiences with meals or activities.
Explore experience ↗◷ 2 hr–3 hr
No city embraces summer quite like Chicago. Join in the celebration with friends and family on this epic fireworks cruise. Get up-close
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Explore experience ↗◷ 1 hr 15 min
See Chicago the Island Party Way. Our floating Tiki Bar offers you the opportunity to take in all the sights and sounds as you relax an
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Explore experience ↗◷ 2 hr
Sail along the magnificent skyline on our Premier Plus Chicago Brunch Cruise. A chef-curated menu of plated brunch specials will deligh
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Explore experience ↗◷ 2 hr
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US
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Explore experience ↗◷ 2 hr
Fine dining and unrivaled skyline views await from the moment you step aboard our Premier Plus Chicago Lunch Cruise. A selection of del
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Explore experience ↗◷ 1 hr 30 min
Fireworks Cruise Aboard Island Time – See the Sparks Fly the Island Party Way! Experience Chicago’s dazzling fireworks like never befor
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Explore experience ↗◷ 1 hr 30 min
This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Wil
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Explore experience ↗◷ 2 hr
Enjoy a picturesque day dining on Lake Michigan with our Premier Chicago Brunch Cruise. You’ll indulge in a chef-prepared buffet meal f
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Explore experience ↗◷ 2 hr
Experience the ultimate Windy City adventure on Chicago’s luxury guided minibus tour! Explore 20+ top landmarks with curated photo stop
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Explore experience ↗◷ 1 hr 30 min
Enjoy a fun and scenic 90-minute Cycleboat Cruise along the beautiful Chicago River! Take in stunning skyline views as you pedal, relax
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Explore experience ↗◷ 2 hr
Set sail for a memorable experience on Lake Michigan with a Signature Chicago Brunch Cruise that is as scenic as it is delicious! You'l
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Explore experience ↗◷ 45 min
Enjoy the Navy Pier Fireworks from the Chicago River. A brief version of Wendella's Lake Michigan Fireworks Cruise, this experience is
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View datesA practical, neighborhood-aware framework for planning a first Chicago visit without reducing the city to a downtown checklist.
