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Chicago
Chicago Sunset Sailing: Private Lake Michigan Cruise Awaits!
120
Overview
Come Sailing at Navy Pier Marina for a stunning sunset sail on Lake Michigan! Enjoy a two-hour private charter for up to six guests, customizable with your choice of music and route. Relax as a licensed captain guides you, offering historical anecdotes and unforgettable skyline views. A perfect, serene escape on the water. 
Highlights
Breathtaking Chicago Skyline Views: Witness the stunning Chicago skyline from the unique vantage point of Lake Michigan, especially magical during sunset.
Personalized Sailing Experience: Customize your sailing route, music, and guest list for a truly bespoke experience tailored to your preferences.
Relaxing and Luxurious Ambiance: Enjoy a comfortable and serene atmosphere on a private charter, perfect for unwinding and creating lasting memories.
Expert US Coast Guard Captain: Benefit from the expertise of a licensed captain, ensuring a safe and informative sailing experience.
Sentiment Analysis
Breathtaking views of the Chicago skyline
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Relaxing and personalized experience
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Knowledgeable and friendly captains
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Perfect for special occasions
Weather-dependent; rescheduling may be necessary
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Gratuities, food, and drinks are not included
Review Summary
Travelers consistently praise the Serene Private Sunset Sail for its stunning views of the Chicago skyline and Lake Michigan, personalized experience, and friendly, knowledgeable captain. Many highlight the flexibility to customize music, route, and guest list, making it ideal for special occasions. The only minor drawbacks mentioned are limited accessibility and the need to bring your own food and drinks, but these are generally not seen as significant issues.
Frequently Asked Questions
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Chicago Food, History & Architecture Walking Tour
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Duration: 270
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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
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Chicago Food Tour: Bites, History & Secret Dishes!
4.9
(859 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).
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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!
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Chicago's West Side Foodie Ride: A Culinary Bike Adventure
4.9
(112 reviews)
Duration: 240
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Chicago's West Side Foodie Ride Bike Tour: Explore Fulton Market, Ukrainian Village, and more on this 4-hour culinary bike tour. Taste Chicago's authentic dishes while learning about the neighborhoods' histories. Concludes with a chocolate tasting. A leisurely paced ride suitable for all fitness levels.
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Chicago Lakefront Bike Tour: Explore Iconic Neighborhoods!
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(241 reviews)
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Bike Tour of Chicago's Lakefront Neighborhoods explores Streeterville, Gold Coast, Old Town, and Lincoln Park. This leisurely 3-hour ride, led by expert guides, cruises the scenic Lakefront Trail. Experience Chicago's culture and architecture on two wheels, creating lasting memories. Suitable for all skill levels.
Chicago
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Discover Chicago's Hidden Gems: An Offbeat Street Art Adventure
4.9
(202 reviews)
Duration: 120
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The Offbeat Street Art Tour unveils Chicago's vibrant murals and graffiti, often missed by locals and tourists. This walking tour explores the city's unique art scene, offering a fresh perspective and memorable photo opportunities. Experience Chicago's creative pulse beyond the typical landmarks.
Nearby Events
Allstate Arena
Dec 31
3:00 PMJeff Dunham Artificial Intelligence Tour at Allstate Arena
Jeff Dunham brings his headline-generating Artificial Intelligence tour to Allstate Arena in Rosemont, Illinois, delivering an evening of ventriloquism and stand-up comedy that has made him one of America's most celebrated comedians. Known for his cast of characters—including the iconic Achmed the Dead Terrorist, Walter the grumpy old man, Peanut the wisecracking dummy, and Bubba J—Dunham combines sharp social commentary with masterful puppet work, creating conversations that tap into nearly every aspect of American life. His nine record-breaking comedy specials have garnered massive audiences, with his NBC primetime special Unhinged ranking as the top non-sports program of its time slot, and his 2008 Christmas special remaining Comedy Central's highest-rated program of all time.
The Artificial Intelligence tour represents Dunham's latest creative evolution, featuring his traditional cast alongside new characters crafted specifically for this tour. Dunham's performances have captivated audiences across more than 20 countries, from the United Kingdom and France to Australia and the Middle East, proving his ability to connect with diverse audiences regardless of cultural background. Allstate Arena, located in the Chicago metropolitan area, stands as a premier entertainment venue hosting world-class comedy, concerts, and sporting events throughout the year.
United Center
Feb 28
5:30 PMWWE Elimination Chamber: Tickets at United Center
WWE Elimination Chamber is set to electrify the United Center in Chicago, promising a night of intense wrestling action. Fans can expect to see their favorite WWE superstars battling it out in the unforgiving Elimination Chamber structure. The event is known for its high-stakes matches and unpredictable outcomes, making it a must-see for wrestling enthusiasts.
WWE Elimination Chamber is one of WWE's signature events, known for its brutal and captivating matches. United Center, located in Chicago, is a renowned venue known for hosting major sporting events and concerts, providing a top-notch experience for all attendees.
American Family Insurance Amphitheater - Summerfest Grounds
Jun 27
7:00 PMPost Malone, Carter Faith Live at Summerfest 2026
Post Malone brings his genre-blurring hits and breakout country crossover energy to the American Family Insurance Amphitheater at Summerfest, with special guest Carter Faith. Fans can expect a high-octane set packed with chart-toppers like 'I Had Some Help,' 'White Iverson,' 'Better Now,' and tracks from his record-breaking album F-1 Trillion, plus surprise collaborations and fan favorites spanning his diamond-certified catalog.
Post Malone has redefined modern hip-hop and pop with a sound that blends rap, rock, and country influences, earning eight 2025 GRAMMY® nominations and headlining Coachella. The American Family Insurance Amphitheater at Summerfest Grounds offers a lakeside festival setting with premium sound and sightlines, making it one of Milwaukee’s most iconic outdoor concert destinations.
Miller High Life Theatre
May 10
2:00 PMSesame Street Live! Elmos Got The Moves Milwaukee Tickets
Sesame Street Live! Elmos Got The Moves brings a vibrant, family-friendly musical performance to Milwaukee’s Miller High Life Theatre, captivating children and parents alike with live-action fun and movement. This energetic show, featuring Elmo and beloved Sesame Street characters, encourages kids to dance, stretch, and play along to classic and new tunes that inspire active learning and joyful engagement.
Celebrated for its interactive approach, Sesame Street Live offers a fresh twist in Elmo’s Got The Moves, blending fun with educational content in a welcoming theater environment. Miller High Life Theatre, known for its central location and lively atmosphere, provides an ideal venue for families seeking memorable live entertainment downtown Milwaukee.
The Auditorium
Mar 13
7:30 PMThe Lord of the Rings Live Concert Chicago Tickets
The Lord of the Rings: The Fellowship of the Ring - Live In Concert at The Auditorium in Chicago offers a breathtaking symphonic experience. This event showcases over 200 musicians performing Howard Shore’s Academy Award-winning score, accompanying the film’s 60-foot screen presentation to bring Middle-earth to life.
The concert celebrates the 25th anniversary of this iconic film, highlighting its timeless appeal. The Auditorium, known for its historic architecture and superb acoustics, provides an immersive setting perfect for both classical music lovers and fans of the epic fantasy saga.
![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.
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