Recent Searches
Clear

Top Chicago Sailing

Saved to wishlist!
Dates
Select Dates
Day Cruises
Day Cruises
Architecture Tours
Architecture Tours
Water Tours
Water Tours
Sightseeing Cruises
Sightseeing Cruises
Sunset Cruises
Sunset Cruises
Night Cruises
Night Cruises
Sightseeing Tours
Sightseeing Tours
Private Sightseeing Tours
Private Sightseeing Tours
City Tours
City Tours
Night Tours
Night Tours
Historical Tours
Historical Tours
Half-day Tours
Half-day Tours
Arts & Design
Arts & Design
On the Water
On the Water
Full-day Tours
Full-day Tours
Likely To Sell Out
Likely To Sell Out
Spring Break
Spring Break
Culinary Tour
Culinary Tour
Adventure Tours
Adventure Tours
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

19 results | All Chicago Tours

Revenue may affect this sort orderWhy you are seeing these results Sort by: Featured

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

star-4.5
290
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. Select from Pirates and Maritime Stories Sail at 1pm, Skyline/Architectural Theme at 3pm and 5pm, and Skyline Sunset Sail at 7pm. This sail is approximately 75 minutes. The ship leaves promptly at the scheduled time, please allow for time to park, off the pier if necessary.
More
  • 1 hour 15 minutes
  • Free Cancellation
From
$49.00
From
$49.00

Educational Tour and Sail Aboard Chicago's Official Flagship Windy 148' Schooner

Educational Tour and Sail Aboard Chicago's Official Flagship Windy 148' Schooner

star-4
44
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
  • Free Cancellation
From
$39.00
From
$39.00

Chicago’s Famous Friday Night Pirates Pub Sail Aboard 148' Tall Ship Windy

Chicago’s Famous Friday Night Pirates Pub Sail Aboard 148' Tall Ship Windy

star-4.5
43
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
  • 2 hours
  • Free Cancellation
From
$59.00
From
$59.00

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
30
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
From
$427.28
per group
From
$427.28
per group

Experience Wed & Sat Chicago Fireworks Aboard Tall Ship Windy from Navy Pier
Likely to Sell OutLikely to Sell Out

Experience Wed & Sat Chicago Fireworks Aboard Tall Ship Windy from Navy Pier

star-4
19
Watch Navy Pier's fireworks display from the deck of a sailboat. During this 75-minute cruise on Lake Michigan, get views of the Chicago city skyline lit up at night and the colorful fireworks exploding over the lake. Listen to your guide's commentary about the city's history and join in on some traditional shipboard working songs if you like.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$79.00
From
$79.00

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
8479
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
More
  • 1 hour 15 minutes
  • Free Cancellation
From
$46.87
From
$46.87

90-Minute Chicago River Architecture Tour
Likely to Sell OutLikely to Sell Out

90-Minute Chicago River Architecture Tour

star-4.5
2162
Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$42.00
From
$42.00

Chicago Lunch Cruise on Lake Michigan
Likely to Sell OutLikely to Sell Out

Chicago Lunch Cruise on Lake Michigan

star-3.5
113
Perfect for families, groups, and corporate outings, the Spirit of Chicago lunch cruise lets you kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.
More
  • 2 hours
From
$81.82
From
$81.82

Lake Michigan Sightseeing Cruise

Lake Michigan Sightseeing Cruise

star-4.5
441
Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride.
More
  • 40 minutes
  • Free Cancellation
From
$28.34
From
$28.34

Chicago Lake and River Architecture Tour
Likely to Sell OutLikely to Sell Out

Chicago Lake and River Architecture Tour

star-4.5
852
Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$42.00
From
$42.00

Chicago Sunset Cruise

Chicago Sunset Cruise

star-4.5
372
Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel in the heart of the Magnificent Mile, and cruise along the Chicago River, where your guide will point out architectural highlights. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$40.00
From
$40.00

Chicago Premier Lake Michigan Lunch Cruise

Chicago Premier Lake Michigan Lunch Cruise

star-4
35
Board a luxurious yacht at Navy Pier for a 2-hour lunch cruise along Chicago’s scenic shoreline. Enjoy a three-course gourmet meal as you take in views of the Windy City from a climate-controlled observation deck, then sip coffee or tea while the yacht’s onboard DJ spins a leisurely afternoon playlist.
More
  • 2 hours
From
$98.22
From
$98.22

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-5
2872
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
More
  • 2 hours
  • Free Cancellation
From
$35.00
From
$35.00

30 Minute Lake Michigan Speedboat Ride

30 Minute Lake Michigan Speedboat Ride

star-4
168
Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.
More
  • 30 minutes
From
$39.21
From
$39.21

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

star-5
14
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
From
$427.28
per group
From
$427.28
per group

Private Evening Sail in Chicago Ending with Navy Pier Fireworks

Private Evening Sail in Chicago Ending with Navy Pier Fireworks

star-5
3
Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Navy Pier fireworks. Over the course of two hours, you’ll sail along Chicago’s beautiful lakefront with a view of the city skyline. You’ll have the perfect vantage point to enjoy the incredible fireworks from Navy Pier. This customizable experience allows you to choose your own, route, music, and guest list.
More
  • 2 hours
  • Free Cancellation
From
$483.96
per group
From
$483.96
per group

Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise
Likely to Sell OutLikely to Sell Out

Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise

star-5
1
You will be treated to a morning of relaxation and fun on Lake Michigan on this sailboat charter. You are in charge of the itinerary, guest list, even music choices! There is a fridge and ice aboard if you would like to bring refreshments (no glass please) and if you are feeling adventurous, you can take a turn at the helm.
More
  • 2 hours
  • Free Cancellation
From
$433.82
per group
From
$433.82
per group

Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise
Likely to Sell OutLikely to Sell Out

Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise

Enjoy a private two and a half hour sailing experience for up to four people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. All charters are NON-SMOKING experiences.
More
  • 2 hours
  • Free Cancellation
From
$474.15
per group
From
$474.15
per group

Chicago Air & Water Show - Best Seat On The Lake - Tall Ship Windy VIP Cruise

Chicago Air & Water Show - Best Seat On The Lake - Tall Ship Windy VIP Cruise

Experience the Air & Water Show Aboard 148' Tall Ship Windy. This is a VIP Charter - Truly the Best Seat in Chicago. Leave our dock and motor to center stage for the best viewing of the Air & Water Show. A don’t miss experience. Chicago’s famous Air and Water Show aboard the Tall Ship Windy is truly a magical event. While the official schedule has yet to be announced, it’s anticipated that the US Navy Blue Angels will return again in 2022 to wow audiences — along with appearances by the USAF F-35A Lightning II Demo, Michael Goulian in his acrobatic Extra 330SC, Rob Holland in the MXS-RH, Susan Dacy in her Super Stearman “Big Red”, and antique military aircraft from the Warbird Heritage Foundation. Also watch for the US Army Golden Knights parachute teams, the U.S. Navy Leap Frogs parachute team, as well as other crowd-pleasing stunts by the AeroShell Aerobatic Team, and a performance by the Chicago Fire Department Air/Sea Rescue team.
More
  • 3 hours
  • Free Cancellation
From
$139.00
From
$139.00

Filters

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 Sailing in Chicago are taking additional safety precautions?
Q:
What Sailing in Chicago are good for avoiding crowds?