Viator Rating : 5 (20 reviews)
Dyvarcity Score : 7.8/10 (Solid Experience)
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. 
Experience DNA Fingerprint
Scores are shown on a scale of 1 to 10, 1 = lowest score, 10 = highest score.
What People Love
Safety (9 - Secure) : Strong feeling of safety and control
Logistics (8 - Seamless) : Smooth and well executed
Instagram Factor (9 - Iconic) : Highly photogenic and memorable
Guide Quality (8 - Exceptional) : Engaging and memorable
Guide Reliability (9 - Dependable) : On time with strong follow-through
What to Watch Out For
Crowd Density (6 - Standard) : Normal crowd, some waiting or tight spots
Upsell Risk (7 - Optional) : Upsells exist but avoidable
Mobility (7 - Moderate) : Some effort required
Pacing (7 - Uneven) : Inconsistent or mixed pacing
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.
This page is synthesized and developed by Dyvarcity Team
More like this
Chicago
$35
Uncover Chicago's Dark Past: A Murder Mystery Adventure!
5.0
(724 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
$100.95
Chicago Food, History & Architecture Walking Tour
4.9
(1152 reviews)
Duration: 270
minutes
Chicago in a Day: Explore Food, History, and Iconic Architecture. This walking tour takes people through the heart of Chicago, showcasing its food, history, and buildings. It's a tasty way to see the city and learn some fun facts.
Visitors will walk along the Riverwalk, see the Wrigley Building, and snap photos at Millennium Park by Cloud Gate, also known as 'The Bean'. The tour also explores hidden spots like the Chicago Pedway and the bustling energy of Chicago's Main Artery. Expert local guides share stories about Chicago's past, from the Prohibition era to the Great Fire.
This tour includes stops at the Chicago Theatre, City Hall-County Building and the Loop. It includes Chicago's famous eats like deep-dish pizza, a Chicago-style hot dog, and Italian beef. The tour is limited to a small group of 12, making it personal and relaxed. This experience is run by a certified B Corp, which means they care about ethical and responsible tourism.
Chicago
$64
Glide Through Chicago: A Lakefront Segway Adventure!
5.0
(345 reviews)
Duration: 120
minutes
The 2-Hour Chicago Lakefront and Museum Campus Segway Tour offers a unique way to explore Chicago's iconic landmarks. Effortlessly glide through Grant Park, visit Buckingham Fountain, and explore Museum Campus. This tour blends sightseeing with adventure, perfect for experiencing Chicago's highlights. Requires basic balance; training provided.
Chicago
$87
Chicago Food Tour: Bites, History & Secret Dishes!
4.9
(867 reviews)
Duration: 180
minutes
Chicago Walking Food Tour With Secret Food Tours lets one savor the Windy City's vibrant flavors! This isn't just a food tour; it's a delicious journey through Chicago's history and culture, one bite at a time. This walking tour explores the famed Chicago Loop District, showcasing world-renowned architecture and public art. See landmarks like the Harold Washington Library Center, walk along LaSalle Street, admire The Flamingo (Calder Sculpture), and catch a glimpse of the Willis Tower (Sears Tower), The Rookery Building, and the Palmer House Hilton.
What can visitors expect? The tour includes the city's biggest food hits, many with roots dating back over 150 years. Imagine tasting the iconic deep-dish pizza, sinking your teeth into an amazing Italian beef sandwich, munching on gourmet popcorn, and savoring other treats. There's also a mouth-watering secret dish that’s revealed only on the day of the tour! The local guide will provide insights along the way.
The tour includes an Italian Beef Sandwich, a brownie, a Chicago-style Hot Dog, a delicious Secret Dish, Deep Dish Pizza with Sausage, and Gourmet Popcorn. It excludes hotel pickup and drop-off, and gratuities (optional).
Chicago
$44
Chicago History Tour: Uncover Downtown's Secrets
5.0
(216 reviews)
Duration: 120
minutes
Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour offers a profound walk through downtown Chicago. It uncovers incredible stories and secrets of the city. This walking tour explores “Da Loop,” peeling back the layers of Chicago to reveal its history and beauty.
Participants can expect an engaging and eye-opening experience. The tour goes inside extraordinary buildings and admires amazing art and architecture, uncovering how it all came to be. Key stops include the Chicago Cultural Center, Chicago Board of Trade Building, Federal Plaza, Reliance Building, Chicago Picasso, Chicago Theatre, and Marshall Field's (Macy's on State Street).
This experience includes all fees and taxes. Expert local guides lead small groups through the city's most iconic landmarks, sharing stories and insights along the way. Get ready to walk and discover the heart of Chicago!
Chicago
$59
Chicago's Iconic Landmarks: A Riotous Bike Adventure
4.9
(233 reviews)
Duration: 180
minutes
Chicago's Ultimate City Bike Tour offers an engaging exploration of iconic landmarks like Millennium Park and the Museum Campus. Led by Bobby's Bike Hike, the leisurely 3-hour ride suits all skill levels. Gain intimate knowledge of Chicago's treasures, perfect for first-time and returning visitors.
Nearby Events
![TWICE [THIS IS FOR] World Tour Chicago 2026](https://images.dyvarcity.com/events-images/dyvarcity_9b95737a3af725eb180f483bc_1abb24e4-d0d8-481f-8c4e-be0a49ed478a_SOURCE.jpg?format=webp&width=600 "Post Image")
United Center
Apr 06
8:00 PMTWICE [THIS IS FOR] World Tour Chicago 2026
TWICE [THIS IS FOR] World Tour brings the global K-pop phenomenon to Chicago's United Center on April 7, 2026. The nine-member girl group continues their electrifying world tour, delivering explosive performances that showcase their signature synchronized choreography, powerful vocals, and infectious energy. TWICE has established themselves as one of the most successful K-pop acts globally, with a devoted fanbase spanning continents and a catalogue of chart-topping hits that resonate across multiple genres.
This tour marks a significant moment for fans eager to witness TWICE's artistry in one of North America's most iconic venues. The United Center, Chicago's premier arena, provides the perfect setting for TWICE's high-production concert experience, combining state-of-the-art staging with an intimate enough atmosphere to capture every member's charisma and connection with the crowd.
United Center
Jun 27
8:00 PMWeird Al Yankovic Chicago: Tickets & 2026 Tour
“Weird Al” Yankovic is bringing his Bigger & Weirder 2026 Tour to the United Center in Chicago, IL! This event promises an evening of hilarious musical parodies and unforgettable stage antics from the reigning king of comedy rock. Expect a career-spanning setlist packed with fan favorites and deep cuts, showcasing Yankovic's unparalleled ability to transform popular songs into comedic masterpieces.
“Weird Al” Yankovic is a pop culture icon known for his clever song parodies and high-energy performances. He has sold millions of albums and won multiple Grammy Awards, solidifying his place in music history. The United Center, a renowned multi-purpose arena in Chicago, is home to the Chicago Bulls and Chicago Blackhawks, and is known for hosting world-class entertainment events.
Rosemont Theatre
Jun 20
12:00 PMDEADMAN ALL STARS LIVE at Rosemont Theatre
DEADMAN ALL STARS LIVE electrifies Rosemont Theatre with high-stakes Old School RuneScape PvP showdowns featuring top content creators like B0aty, Torvesta, and Odablock. This multimedia spectacle showcases team drafts, intense battles, and epic finales in the pinnacle of competitive Deadman mode, drawing fans with its chaotic energy and strategic brilliance.
DEADMAN ALL STARS captivates as a tournament where captains assemble squads of creators for week-long grinds culminating in deathmatches under Deadman rules. Rosemont Theatre, a premier venue near Chicago O'Hare, hosts this multimedia extravaganza with state-of-the-art production.
United Center
May 01
8:00 PMDemi Lovato: It's Not That Deep Tour at United Center
Demi Lovato brings her highly anticipated 'It's Not That Deep Tour' to the iconic United Center in Chicago, promising an unforgettable night of pop anthems and raw, emotional performances. Known for her powerful vocals and candid stage presence, Demi is set to showcase new music and fan favorites in one of the city’s most celebrated arenas.
Demi Lovato continues to captivate audiences with her evolving artistry and resilience, making each concert a deeply personal experience. The United Center, home to the Chicago Bulls and Blackhawks, is renowned for its state-of-the-art acoustics, vibrant atmosphere, and history of hosting legendary concerts.
Huntington Bank Pavilion at Northerly Island
May 20
7:30 PMKhalid & Lauv Chicago Tickets: R&B Summer Tour
Khalid and Lauv co-headline the It's Always Summer Somewhere Tour at Huntington Bank Pavilion at Northerly Island, delivering a night of smooth R&B and pop vibes. After a long hiatus, Khalid returns with his signature emotional synths and hits that defined a generation, joined by Lauv's heartfelt opener for an unforgettable double-header of summer anthems.
Khalid's music, from breakout tracks like those evoking young love and nostalgia, resonates deeply with fans who grew up on his sounds through headphones and car rides, promising lake breezes and crowd sing-alongs. The venue offers a scenic lakeside setting in Chicago's urban oasis.
Pabst Theater
Nov 10
7:00 PMDaniel Sloss: BITTER Tour at Pabst Theater
Daniel Sloss: BITTER brings the Scottish comedy powerhouse to Milwaukee's Pabst Theater for his brand new tour. Known for Netflix specials DARK and Jigsaw, and recent releases like SOCIO and HUBRIS, Sloss delivers razor-sharp stand-up that has sold out global tours and broken records at the Edinburgh Fringe.[1][5][7]
Sloss, who started performing at 16 under Frankie Boyle's guidance, became the youngest comedian for a solo West End season at 19 and has appeared on Conan ten times. The historic Pabst Theater, a Milwaukee landmark, offers an intimate setting for his provocative humor on topics like religion and death.[1][2][5]
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