Chicago (Expert 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
Discover Chicago's Iconic Loop: Architecture, Art & History Walking Tour
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
$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
$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.
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
$539
4.9
(201 reviews)
Chicago Private Custom City Tour offers a personalized exploration of Chicago with hotel pick-up. Enjoy a 3-4 hour chauffeured tour, led by knowledgeable guides. Stops include Millennium Park and Museum Campus. Interactive and entertaining, this tour covers Chicago's history, architecture, and culture. Concludes with drop-off at your preferred downtown location.
Chicago
$85.5
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.
Chicago
$85.5
5.0
(152 reviews)
Duration: 150
minutes
Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max. This tour lets people see amazing art without waiting in long lines. It is a walking tour that is great for people who like art and history.
What to Expect: The Art Institute of Chicago is a very popular museum, just like the Met in New York or the Louvre in Paris. On this 2.5-hour tour, a friendly guide will take a small group (8 people max) to see the most famous artworks. Some of the art you might see includes *Paris Street, Rainy Day*, *Sunday on La Grande Jatte*, and *Nighthawks*. But sometimes, art is not there because it is being fixed or moved.
This tour includes all entrance fees and a guide who knows a lot about art. It does not include tips for the guide or rides to and from your hotel. It's easy to get to the museum by taxi or UBER.
Chicago
$849
4.8
(126 reviews)
Duration: 45
minutes
Experience Chicago like never before with a Private 45-Minute Helicopter Tour. Enjoy breathtaking panoramic views of the city's iconic skyline with family or friends. This exclusive tour offers a thrilling and intimate experience, complete with live commentary and unparalleled photo opportunities. An unforgettable adventure awaits!
Chicago
$37
4.8
(1634 reviews)
Duration: 90
minutes
The Chicago River 90-Minute Architecture Boat Tour lets people see amazing buildings along the Chicago River. Expert guides tell stories about the city's famous places. This tour is for everyone!
You'll see places like the Wrigley Building and the Willis Tower. The boat goes to Navy Pier and even to Chinatown! You can learn about old buildings and new ones being built.
This boat has seats inside with air conditioning and windows. There are also seats outside if you want to be in the sun. There are bathrooms on the boat. You can buy drinks and snacks, and parking is close by. This tour shows you the best of Chicago from the river!
Chicago
$41
4.9
(91 reviews)
Trickery Chicago Magic Show offers an intimate, hilarious, and sometimes outrageous experience. Located at 3453 N Halsted Street, this BYOB venue (21+) provides cups and openers. Doors open 15 minutes before showtime for this one-hour performance. Prepare for mind-blowing illusions and unforgettable laughs!
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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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