Top Picks for Chicago Yachts & sailboats

Discover 1 Yachts & sailboats in Chicago on Trip.com, updated November 23, 2025, with experiences lasting from 1 to 2 hours. Find the perfect adventure for your day!

From PHP 3,433.45 per person, with an average total of PHP 3,433.45. Choose the option that suits your plan.

Now on Trip.com: "Chicago Architecture Cruise Experience from Michigan Avenue|Depart from Navy Pier", a 1-hour adventure in Chicago!

The next available day tour departs on November 24, 2025. Book now to secure your spot!

Chicago Yachts & sailboats usually take about 1 hours — perfect for a relaxed, immersive experience!

100% of Chicago Yachts & sailboats now offer English-speaking guides

November is perfect for visiting Chicago! Choose from Yachts & sailboats available day tours, including seasonal hits like Chicago Architecture Cruise Experience from Michigan Avenue|Depart from Navy Pier.