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3 results | All Chicago Tours

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Chicago Skyline Tall Ship Cruise
Likely to Sell OutLikely to Sell Out

Chicago Skyline Tall Ship Cruise

star-4.5
59
Escape the bustle of the city on a sailboat tour through Lake Michigan with a convenient departure from Navy Pier. The cruise offers plenty of frame–worthy photo opportunities, including sweeping views of the Chicago skyline rarely seen by visitors. As a popular choice for both locals and visitors, your experience is guaranteed to be family–friendly and tailored to your needs.
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  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
$44.00
From
$44.00
Taking safety measures

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
Likely to Sell OutLikely to Sell Out

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

star-5
7
If you’ve ever dreamed of sailing away on your own private sailboat, this is the perfect excursion for you. You and up to five other invited guests will have the exclusive use of a sailboat, complete with captain and crew for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you could even take a turn at the helm.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$427.28
per group
From
$427.28
per group
Taking safety measures

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
Likely to Sell OutLikely to Sell Out

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

star-5
8
Soak up the views of Lake Michigan and the Chicago skyline with a 2-hour sailing tour. This private charter is completely customizable, giving you the chance to choose your music, route, and up to 5 additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$427.28
per group
From
$427.28
per group
Taking safety measures

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What people are saying about Sailing in Chicago

star-5
Chicago Skyline Tall Ship Cruise
"Overall great experience! Great views, great crew, great vibes and delicious drinks! Definitely recommend 👌🏼"..."
star-5
Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago
"Very pleased with the entire experience. Will definitely do it again! A small group of us (6) had an awesome time on the Lake with wonderful views of the Skyline & Navy Pier. Fantastic experience for both locals and tourists."..."
star-5
Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago
"It was truly the best choice to do something different, special, and romantic to celebrate my Wife's birthday. We recently moved to Chicago and was the first time we saw the city from the inner lake. The views and sunset were truly spectacular. Captain Mike was quite friendly and professional. We felt quite safe under the circumstances."..."

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
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