Recent Searches
Clear

Top Chicago Sailing

Travel update: We’re doing our best to help keep you safe and your plans flexible. Learn more.

Read More
When are you traveling?
Select Dates
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
Search tours and activities you can do from home.

You are viewing Virtual Experiences in Chicago. See more Virtual Experiences around the globe. 🌎

Price
$0
$500+
Duration
Time of Day
RatingClear
Specials

Travel update: We’re doing our best to help keep you safe and your plans flexible. Learn more.

Read More
Select Dates
Today
Tomorrow

4 Chicago Sailing | All Chicago Tours

Sort by:Featured

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

star-5
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

Chicago Lakeside Architecture Tour

Chicago Lakeside Architecture Tour

star-4.5
Get views of Chicago's famous architecture from the deck of a boat during this sailing excursion. Learn about the people, plans, and persistence that shaped Chicago's architecture along the shoreline. Hear about the city's historical maritime roots to modern science and technology through your guide's commentary while taking advantage of great photo ops. Choose between an afternoon or early evening departure and relax as you enjoy the sights. 
More
  • 1 hour 15 minutes
From
$40.46
From
$40.46

Real Pirates of the Inland Seas: Chicago Pirate-Themed Sailboat Tour

Real Pirates of the Inland Seas: Chicago Pirate-Themed Sailboat Tour

star-4.5
Experience Lake Michigan from a perspective rare to visitors and locals alike on a pirate–themed sailboat tour. Your guides tell true but little–known stories about pirates, battles, and treasure hunts as you cruise past sweeping views of the Chicago skyline. Relax on deck while or join your guides for an interactive experience—the flexibility of the tour makes this a popular choice for families with children.
More
  • 1 hour 15 minutes
  • Free Cancellation
From
$40.46
From
$40.46

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

star-5
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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$427.28
per group
From
$427.28
per group
Taking safety measures

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Sailing in Chicago?
Q:
What tours in Chicago are taking additional safety precautions?
Q:
What tours in Chicago are good for avoiding crowds?