Chicago (Dependable Guides)
Walking Tour: Underground Chicago via the Pedway is an adventure that explores the city's secret underground tunnel system, called the Pedway, and some special sights above ground. This walking tour is perfect for anyone who wants to see a different side of Chicago and learn about its history and culture.
The tour starts in the Swissotel lobby with a short introduction to the Pedway. Guests will go underground to visit the Cultural Center and see the beautiful Tiffany Dome. The tour continues through the Pedway to Macy's, where visitors can admire the Tiffany ceiling and the famous Walnut Room. Then the tour heads west to see the Picasso sculpture in Daley Plaza and the Chicago Temple with its Sky Chapel.
After a quick train ride, the tour arrives at the start of Route 66, where guests can take photos with the Art Institute's lion statues. Finally, the tour visits Millennium Park to see Cloud Gate (The Bean), Lurie Gardens, and Crown Fountain. The tour includes transit tickets and a local expert guide. Gratuities, food, and drinks are not included.
Duration: 180
minutes
Price from
$65
Chicago's Hidden Pedway: Underground Walking Adventure
Relive 'Ferris Bueller's Day Off' Through Art: An Iconic Chicago Museum Tour
Wicker Park's Architectural Gems: A Historic Homes Walking Tour
Chicago Shoreline Adventure: High-Speed History & Thrilling Spins!
Chicago's Best Bites: A Delicious Bike & Brews Tour
Chicago
$89
5.0
(95 reviews)
Duration: 90
minutes
Small-Group Sightseeing Boat Tour in Chicago is the ultimate way to see the city! This custom experience gives folks amazing views and photo opportunities of Chicago's famous skyline.
The boat zips around local waterways, passing sights like Navy Pier and Soldier Field. See Fort Dearborn, the Vietnam Memorial, Wolf Point, and the Shedd Aquarium. This tour gives a unique and personal look at the City!
Folks will ride in a safe and strong Rigid Inflatable Boat (RIB), originally built for the US NAVY. Life jackets are provided. The boat tour focuses on the Chicago skyline, including views of the Adler Planetarium. Please bring your own bottled water and sunscreen.
Chicago
$44
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
$169
5.0
(31 reviews)
Duration: 60
minutes
The Chicago Insta Walk offers a fun, relaxed exploration of the city, capturing stylish photos with digital and Polaroid cameras. Receive 100 digital photos (10 color-corrected) and 5 Polaroid prints for unique souvenirs. A friendly tour guide helps you discover Chicago from a fresh perspective.
Chicago
$35
5.0
(54 reviews)
Duration: 90
minutes
Chicago Crime and Ghosts Walking Tour takes people back in time to the days of Al Capone and spooky ghost stories. This walking tour explores Chicago's dark past, blending true crime history, ghost stories, and famous buildings.
Walk along the Chicago River, where some of the city's most infamous events happened. Visit old speakeasies from the Prohibition era and spots where John Dillinger hung out. See the Chicago Picasso and the Theater District, a site of gangster activity. Step inside famous hotels and see the Art Institute, where history whispers after dark. An expert historian guides you, sharing stories of beauty and horror from one of America's most famous periods.
This tour gives you special access to places connected to famous events. Learn about the city's architectural landmarks and haunted locations. It includes an expert tour guide, and access inside famous hotels. Tips and gratuities for the tour guide are not included. The tour ends near a convenient location for continued exploration.
Chicago
$215
5.0
(83 reviews)
Duration: 120
minutes
Art Institute of Chicago Private Expert Guided Tour. Explore one of the world's finest art museums with a local expert! This private 2-hour tour is perfect for art lovers of all levels.
Visitors can expect to see famous artworks from different times and places. The expert guides will tell the stories behind the art, making it fun and easy to understand. You'll see amazing paintings, sculptures, and more!
This tour includes early admission on morning tours, skip-the-line access, and all entrance fees. It's wheelchair-friendly, so everyone can join. Gratuities and transportation to and from the museum are not included. Discover the Art Institute of Chicago with someone who knows and loves art!
Chicago
$507.96
5.0
(70 reviews)
Duration: 120
minutes
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago, offers a memorable two-hour private sailing adventure for up to six people. Guests can relax and enjoy stunning views of the Chicago skyline with a US Coast Guard licensed captain.
The flexibility of a private charter allows guests to customize their experience. From music selection to sailing route, the trip can be tailored to individual preferences. Key sights include the Navy Pier Marina, the iconic Navy Pier itself, the breathtaking Chicago Skyline, Adler Planetarium, Soldier Field, and Buckingham Fountain.
This experience includes the use of Bluetooth speakers, the Navy Pier facility fee, all taxes, and a professional US Coast Guard licensed captain. Food, drinks, gratuities, and parking are not included.
Chicago
$507.96
5.0
(27 reviews)
Duration: 120
minutes
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.
Milwaukee
$79
5.0
(48 reviews)
Duration: 180
minutes
Old Milwaukee Guided E-Bike Tour: Explore 17½ miles of Milwaukee's best spots with ease. Discover historic neighborhoods, iconic architecture like the 8 million brick city hall, and scenic parks. Enjoy lake and river views while understanding Milwaukee's rich past and bright future on this ride through the whole city.
Chicago
$35
5.0
(326 reviews)
Chicago Architecture and True Crime History Tour offers a thrilling exploration of Chicago's iconic skyline intertwined with its intriguing, sometimes dark, past. Inspired by 'Devil in the White City,' this guided walking tour unveils secrets hidden within architectural marvels and overlooked landmarks that are typically missed by boat tours.
Participants can anticipate venturing to significant sites, including the Marshall Field's Building (Macy's on State Street), a testament to architectural grandeur, and the modern Chase Tower, learning about their historical and cultural impact on Chicago. Along the way, the tour guide will share true crime stories that will transport participants to another time.
This experience includes the expertise of a local guide, and excludes gratuity. This tour is perfect for those seeking a unique perspective on Chicago's history and architecture.
Chicago
$47.95
4.9
(326 reviews)
Duration: 75
minutes
The Escape Game Chicago: Epic 60-Minute Adventures in River North offers a thrilling and immersive experience for everyone. Located near Michigan Avenue, this adventure is perfect for pairing with dinner and drinks in Chicago's vibrant River North neighborhood. Some local favorites within walking distance include Big Bowl Chinese, Gordon Ramsay Burger, and Pizzeria Duo, serving up authentic Chicago deep dish.
Participants work together to discover clues, solve puzzles, and complete a mission within 60 minutes. Teamwork, communication, and a sense of adventure are key! A dedicated game guide helps as needed. Choose from five unique themes. Gold Rush tasks players with finding hidden gold. Prison Break challenges them to escape from an evil warden. Special Ops: Mysterious Market sends them undercover as secret agents. The Heist requires recovering a stolen masterpiece. Mission: Mars launches players into space from the Red Planet.
This experience includes admission to play one adventure. It excludes hotel pick-up and drop-off. Escape Game Chicago promises a unique, premium experience. With award-winning escape rooms and fast customer support, it is an unforgettable activity.
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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.
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