5 (20)
Chicago
Chicago Tall Ship Windy: Skyline Sail on Lake Michigan
75
Overview
Experience the beauty of Chicago with a sail on the Tall Ship Windy, Chicago's Official Tall Ship Ambassador. This relaxing adventure on Lake Michigan offers stunning views and fresh air.
See Chicago's iconic skyline from a unique vantage point. Guests can join the friendly crew to help raise the sails or simply relax and enjoy the ride. The Tall Ship Windy boasts a full bar and gift shop for added enjoyment. The cruise takes you along the Lake Michigan shoreline, offering views of the Chicago Skyline and the vast expanse of Lake Michigan.
This tour includes access to a restroom on board. Alcoholic beverages, snacks, and gratuities are not included. It's a fantastic way to see Chicago that all ages can enjoy. 
Highlights
See Chicago's Skyline: Enjoy amazing views of the city from Lake Michigan.
Join the Crew: Help raise the sails with the friendly crew.
Fun for All Ages: A great experience for families and friends.
Relax on Lake Michigan: Enjoy a relaxing sailing adventure with fresh air.
Sentiment Analysis
Customers loved the helpful and attentive crew.
-
Many enjoyed learning about Chicago's history and how to tie knots.
-
The views are great for family photos.
-
Kids were entertained with pirate stories.
Some people might not enjoy this specific type of cruise.
-
One customer mentioned that if you want something informative it may not be a cup of tea.
The Journey
Tall Ship Windy & Chicago Skyline
Set sail on the Tall Ship Windy, a magnificent four-masted schooner, and witness Chicago's iconic skyline like never before. This isn't just a boat ride; it's a journey through maritime history combined with unparalleled views of architectural landmarks. Experience the thrill of sailing on Lake Michigan while gazing at masterpieces like the Willis Tower and John Hancock Center from a unique perspective. It's a must-do for architecture enthusiasts and anyone seeking breathtaking photo opportunities.
Lake Michigan Shoreline
Board and disembark at this location, offering easy access to the shimmering expanse of Lake Michigan. Here, the vibrant energy of Chicago meets the serene beauty of the lake. This spot serves as the perfect gateway to various lake activities and provides stunning views of the city's skyline, ensuring a memorable starting and ending point to your aquatic adventure. The constant motion of boat activity and the proximity to the water creates an invigorating atmosphere.
Lake Michigan
Venture onto Lake Michigan, one of the five Great Lakes of North America, offering a vast expanse of shimmering blue waters. Experience the thrill of sailing, the tranquility of the open water, and the breathtaking views of the Chicago skyline from a unique perspective. Lake Michigan is not just a body of water; it's a dynamic ecosystem and a vital part of Chicago's identity, offering recreational activities, stunning scenery, and a sense of awe-inspiring natural beauty.
Know Before You Go
This experience includes access to a restroom on board for your comfort. Please note that alcoholic beverages and snacks are not included in the ticket price, but are available for purchase. Gratuities for the crew are also not included. Meet up at the Tall Ship Windy for your sailing adventure.
Hot Tip
Based on reviews, consider bringing kids along! The crew often entertains children with stories and knot-tying lessons, making it a memorable experience for the whole family.
Review Summary
Travelers consistently praise the Chicago Skyline Sail on Tall Ship Windy for its stunning views, friendly crew, and relaxing atmosphere. Many highlight the opportunity to help raise the sails and enjoy the city skyline from the water. The most common feedback is that the experience is enjoyable for all ages, though some wish the sail were longer. The main drawbacks mentioned are the lack of accessibility for those with mobility issues and the strict non-refundable cancellation policy.
Frequently Asked Questions
PMore like this
Milwaukee
$125
Milwaukee's Skyline: An Unforgettable Private Helicopter Tour
4.9
(9 reviews)
Experience Milwaukee like never before with a private helicopter tour over the city's iconic landmarks. Soar above the Milwaukee River, Hoan Bridge, and Art Museum. Enjoy a unique perspective of the entire cityscape from your private helicopter with a professional pilot/guide, headsets provided. Capture memories with optional photo purchase upon landing. An unforgettable adventure!
Chicago
$42.78
Chicago Thrills: Lake Michigan Speedboat Adventure!
4.1
(333 reviews)
Duration: 30
minutes
Experience Chicago's skyline with the Lake Michigan 30-Minute Speedboat Ride! Departing from Navy Pier, enjoy a thrilling speedboat tour along the shoreline, coupled with insightful descriptions of Chicago's iconic architecture. This family-friendly adventure offers unobstructed views and combines excitement with engaging commentary.
Chicago
$35
Chicago's Dazzling Architecture: Interiors Walking Tour
5.0
(1455 reviews)
Duration: 120
minutes
Original Chicago Architecture Interiors Tour: Dazzling Interiors takes guests on a journey through some of the city's most breathtaking interior spaces. Many people pass by these hidden gems every day without realizing what's inside. This walking tour, led by an experienced local guide, reveals the stunning beauty within.
Guests will explore architectural wonders, from turn-of-the-century stained glass mosaics to soaring Art Deco designs from the Roaring 20s. Key stops include the iconic Art Deco Building, Surprise Interiors, and the Chicago Cultural Center. Each location offers a unique glimpse into Chicago's rich history and artistic heritage.
The tour includes a knowledgeable local guide who provides insights and stories about each location. Gratuities are not included. Prepare to be amazed by the hidden beauty that lies within Chicago's architectural treasures.
Chicago
$35
Uncover Chicago's Dark Past: A Murder Mystery Adventure!
5.0
(710 reviews)
Duration: 120
minutes
The Chicago Murder Mystery Tour blends history and intrigue as you solve a fictional crime. Explore famous neighborhoods, delve into true crime legends, and play detective. Enjoy interactive gameplay and souvenir mugshot photos. Perfect for history buffs and true crime fans seeking a unique, immersive city experience, requiring walking and observation skills.
Chicago
$44.43
Chicago Architecture River Cruise: See the Skyline!
4.8
(15737 reviews)
Duration: 60
minutes
Chicago Architecture River Cruise lets people see Chicago in a fun way. This boat tour goes down the Chicago River. People can see over 40 famous buildings, like the John Hancock Center and the Wrigley Building.
An expert guide tells people about the buildings and their history. It's a great way for everyone to see Chicago, even if they live there! People can sit and relax while seeing the city's amazing buildings. The boat goes to places like the Chicago River, Chicago Skyline, Navy Pier, and the Willis Tower. People will learn a lot about the city's buildings as they float by.
This boat tour includes live talking from an expert, and a tour of the Chicago River. Drinks cost extra to purchase, and there is no WIFI on the boat.
Chicago
$90.01
Chicago Art Institute: Skip-the-Line Private Tour
5.0
(271 reviews)
Duration: 150
minutes
Private Art Institute of Chicago Skip-the-Line Guided Tour. This is a special walking tour for people who love art and want to see the best pieces at the Art Institute of Chicago without waiting in long lines. The tour is just for the group and a guide, so it feels personal.
What to Expect: The tour visits famous artworks like 'Paris Street, Rainy Day' and 'Sunday on La Grande Jatte'. People will also see 'Nighthawks' and 'The Old Guitarist'. The guide shares stories about the art and artists. The Art Institute of Chicago is a very big museum with lots of famous art. It has art from all over the world and different times in history.
This private tour lasts for 2.5 hours and includes a professional tour guide just for the group. It also includes all entrance fees. The tour is wheelchair friendly. This tour does not include hotel pickup or drop-off, but the guide suggests using UBER or a taxi. Gratuities (tips) are not included in the price.
Nearby Events
United Center
Oct 03
7:30 PMDoja Cat Tour Ma Vie World Tour at United Center
Doja Cat brings her highly anticipated Tour Ma Vie World Tour to the United Center in Chicago, delivering a dynamic live experience that blends her signature hip-hop flair with global pop influences. Fans can expect a high-energy setlist featuring hits like 'Paint The Town Red,' 'Woman,' and 'Kiss Me More,' as Doja Cat showcases her evolution as one of music’s most innovative performers.
United Center, home to the Chicago Bulls and Blackhawks, is renowned for its state-of-the-art sound and electric atmosphere, making it the perfect venue for Doja Cat’s largest world tour to date. This stop is part of a global journey that marks her first time headlining major arenas across multiple continents.
NOW Arena
Dec 27
6:00 PMAEW Worlds End 2025 Tickets | NOW Arena
AEW Presents Worlds End brings All Elite Wrestling's premier annual pay-per-view event to NOW Arena in Hoffman Estates, Illinois, showcasing the promotion's top stars competing in high-stakes matches. This third annual Worlds End event will feature the highly anticipated finals of the 2025 Continental Classic tournament and matches for the AEW Unified Championship, delivering the wrestling spectacle that fans have come to expect from one of the industry's leading promotions.
All Elite Wrestling has established itself as a major force in professional wrestling since its debut in 2019, consistently delivering innovative storytelling and athletic performances that captivate global audiences. NOW Arena has become a cornerstone venue in AEW's schedule, having hosted multiple premium live events and earning its reputation as a premier destination for wrestling fans in the Chicago metropolitan area.
Hard Rock Live Rockford
Jan 23
7:00 PMMartin Lawrence Live in Rockford - Jan 23, 2026
Martin Lawrence brings his legendary comedy to Hard Rock Live Rockford on January 23, 2026, delivering an evening of stand-up performance from one of America's most iconic comedians. The German-born entertainer rose to prominence in the 1990s as the star of the groundbreaking Fox sitcom Martin, which became a cultural phenomenon and helped establish him as a master of character comedy and improvisational humor. Beyond his sitcom success, Lawrence has maintained a thriving career spanning decades, from hosting HBO's influential Def Comedy Jam to starring in blockbuster action-comedies like Bad Boys alongside Will Smith.
Lawrence's comedy is known for its edgy, insightful perspective on social stereotypes and contemporary culture, a style that earned him an NAACP Image Award and respect from critics who recognized his work as both entertaining and socially engaged. His live performances showcase the same versatility and comedic timing that made him a household name, blending sharp observations with his signature humor. Hard Rock Live Rockford, located in Illinois, provides an intimate venue setting for experiencing Lawrence's dynamic stage presence and comedy craft.
Soldier Field
Jun 06
1:30 PMBuy Tickets: U.S. Men's National Team vs Germany at Soldier Field
The U.S. Men's National Team vs Germany Coca-Cola Send-Off Match at Soldier Field in Chicago offers an electrifying international soccer showdown. This event features two of the world's most storied soccer teams competing in a highly anticipated send-off match that promises thrilling moments.
The U.S. Men's National Soccer Team continues to build momentum with fresh talent and rising global prominence, while Germany remains a powerhouse with a storied World Cup legacy. Soldier Field, renowned for its iconic stadium architecture and historic sporting events, provides an unforgettable backdrop for this spectacular soccer experience.
Huntington Bank Pavilion at Northerly Island
Jun 25
6:30 PMMartin Garrix Americas Tour Chicago Tickets
Martin Garrix brings his biggest Americas Tour to Huntington Bank Pavilion at Northerly Island in Chicago. The Dutch DJ and producer delivers his world-renowned high-energy live production, featuring massive drops and crowd-pleasing anthems across his 16-city North and South American run launching in May 2026.
Known for global hits like 'Animals' that propelled him to stardom at age 17, Martin Garrix continues to dominate electronic music with innovative sets and collaborations. Huntington Bank Pavilion at Northerly Island offers stunning lakeside views amid Chicago's skyline, enhancing the immersive concert experience.
Soldier Field
Jun 27
5:30 PMEd Sheeran LOOP Tour: Live at Soldier Field Chicago
Ed Sheeran brings his highly anticipated LOOP Tour to Soldier Field in Chicago, delivering an unforgettable evening of pop music and heartfelt storytelling. Known for his chart-topping hits and intimate live performances, Sheeran is set to captivate fans with new music and fan favorites in one of the city’s most iconic venues.
Soldier Field, home of the Chicago Bears and a historic landmark on the shores of Lake Michigan, offers a world-class concert experience with sweeping views and top-tier acoustics. The LOOP Tour marks Sheeran’s first major North American stadium run since his record-breaking Divide Tour, making this a must-see event for music lovers.
Chicago Best Things to Do: Concerts, Helicopter & Food Tours
The Chicago skyline is hiding a secret- a ton of them, actually. It’s more than a view: it’s got adventures you're meant to explore. Breathe in the winds and excitement of a helicopter tour, party at top concerts, or dive into food and pizza tours. Walk beside history on a gangster mob tour, take a fireboat or bus tour. Looking to get wild tonight? Find events going on sooner than tomorrow, from EDM to country concerts. Check all your bucket list boxes, and live stories you’ll remember forever.
View Chicago Activities