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1,546 reviews
To truly appreciate Chicago's famous skyline, admire it from the water on this top-rated Lake Michigan architecture cruise. While most sightseeing boats remain on the Chicago River, this one gives you a panoramic...read more
Taking safety measures
1–2 hours
Best Seller
from US$42.00
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641 reviews
If your feet need a break from the city streets, a short skyline cruise is the perfect way to see the best of Chicago without breaking a sweat. Offered regularly throughout the day, it’s easy to fit this tour into...read more
Taking safety measures
40 minutes
from US$34.93
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258 reviews
See the beauty of Chicago from a new vantage point by going on this scenic cruise along the Chicago River and Lake Michigan shoreline. It’s a great way to spot multiple top Chicago landmarks in a short space of...read more
1–2 hours
from US$44.00
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187 reviews
Explore the lakefront districts of Chicago's North Side on a bike tour along quiet streets and waterside paths in the Windy City. You cover ground quickly as you pedal with your guide from Lake Shore Drive to the...read more
Taking safety measures
3 hours
from US$54.99
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508 reviews
Chicago offers amazing historical and culinary adventures, and this bike and food tour allows you to experience both while leaving the navigation to a guide. Hop on a provided bike and pedal around 13 miles (21...read more
Taking safety measures
4 hours
from US$89.99
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5 reviews
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Taking safety measures
3 hours
from US$54.99
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431 reviews
Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. Windy...read more
Taking safety measures
1–2 hours
from US$59.00
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50 reviews
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3 hours
from US$245.88
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73 reviews
The educational sail aboard Chicago's Official Flagship Windy departs at 11am Thursday thru Monday...read more
1–2 hours
LIKELY TO SELL OUT*
from US$39.00
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1 review
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Taking safety measures
2 hours
from US$300.00
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26 reviews
The famous Tall Ship Windy sunset sail is truly famous. Used in many world-renown photos, backdrops for special events, weddings, or just an evening out, the sunset sail aboard one of the only four-mast Schooners...read more
Taking safety measures
1–2 hours
from US$59.00
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158 reviews
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2 hours
from US$47.00
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61 reviews
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1–2 hours
from US$47.00
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Celebrate the magic of the season on the water with a Christmas Eve Premier Dinner Cruise in Washington DC. You and your guests will enjoy a holiday 3-course, plated dinner freshly prepared by our chef, full bar...read more
3 hours
from US$188.47
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5 reviews
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3 hours
from US$273.26
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