Top Chicago Cultural & Theme Tours

Chicago Architecture River Cruise

• 2,460 reviews
• Cruise down the Chicago River to see the city's famous architecture on this 75-minute tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like the Aon Center, the Wrigley Building and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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Chicago Crime and Mob Tour

• 374 reviews
• Explore Chicago's gangster past on this 1.5-hour mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
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Gangsters and Ghosts Tour in Chicago

• 9 reviews
• Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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Chicago Prohibition Tour

• 107 reviews
• Visit four historic bars in operation since Prohibition in Chicago, and learn from a knowledgeable guide about the surreptitious world of the speakeasy. This adults-only tour takes you by coach to once-illicit establishments in Old Town, Wicker Park and the Chicago Loop where liquor, jazz and mobsters ruled. You’ll hear about Chicago gangsters like Al Capone and learn the historical context for the decade-long ban of alcohol. If you’d like, you can purchase recommended craft cocktails and signature drinks of the 1920s.
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Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

• 95 reviews
• Venture inside renowned Chicago landmarks, elegant lobbies, and underground corridors on this 2-hour walking tour. Your expert guide will share insights about interior architectural features of this design-rich city — from mosaic domes to the sprawling Chicago Pedway System — bringing the details of the Windy City into vivid focus. Stop to admire Chase Tower, the Marshall Field and Company Building, the Chicago Cultural Center, and more.
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Art Institute of Chicago Fast Pass Admission

• 45 reviews
• Explore the Art Institute, Chicago’s world-class art museum and the second-largest in the United States, with this Fast Pass Admission ticket. Situated in Grant Park, the museum’s incredible range of impressionist, post-impressionist, modern and contemporary works is near the top of the list of Chicago’s must-see sights. Among the artists on display are works by Pollack, van Gogh, Renoir, Monet and Picasso plus, plus a striking new Modern Wing and cutting edge graphic and industrial design.With mobile tickets, simply scan your phone for direct entry into the Art Institute.
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Chicago Land and River Architecture Tour: North and South Shores

• Whether you’re short on time or want to orient yourself to Chicago, a 3.5-hour land and river tour is the perfect option. The comprehensive itinerary takes you through both the North and South sides. Listen as your guide tells insider stories about the people who shaped the city. After the land tour, rest your feet and see the city from a unique vantage point during a 90-minute river cruise.
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Haunted Chicago Segway Tour

• 15 reviews
• Glide through the city of Chicago by moonlight on this haunted Segway tour. Follow your costumed local guide for 2 hours as they show you the sites of some of the most gruesome murders and disasters in Chicago's colorful history. See Chicago's iconic landmarks lit up during the spookiest time of year and hear about the mysterious, haunted history of this storied city.
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Urban Sketching Downtown Chicago with a Watercolor Artist

• We will be sketching the urban landscape of downtown Chicago using pencil, pen, and watercolors. During this two and a half hour experience you will learn the basics of Urban Sketching and complete at least one piece of art work. I'll show you how to let your guard down and your inner artist out. During the cooler days, if it's raining, or snowing we'll sketch inside at one of the many Chicago architectural gems.
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Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

• 7 reviews
• See the overlooked highlights of Chicago’s Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city’s architecture, art and history while visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.
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Chicago Film Tour

• 49 reviews
• Take a film-lover's exploration of the Windy City during this 2-hour Chicago movie tour. Whether you're a movie die-hard or just looking for a unique way to explore Chicago, this tour offers a 30 mile (48km) trip by air-conditioned coach past the locations where movies such as Ferris Bueller's Day Off, The Dark Knight and Transformers 3 were filmed. In addition to seeing the filming locations, you'll also have a chance to visit iconic Chicago neighborhoods including Lincoln Park, Wrigleyville, the Gold Coast and Old Town among others. This Chicago film tour also includes a guide.
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Saturday Chicago Pizza History and Tastings Bus Tour

• Foodies will enjoy this tour of Chicago that focuses on one of the city’s most popular dishes: pizza. Although your guide can’t tell you once and for all whether Chicago or New York has the best pizza in the USA, they will teach you about Chicago’s ten different types of pizza, let you sample four, and give you exclusive access to pizza kitchens. A fun tour for all pizza lovers.
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Private Haunted History of Chicago Ghost Tour

• Discover spooky stories in the Windy City on a private haunted history tour. Visit places with names such as the Murder Castle and Death Alley, and hear about Al Capone and the Old Congress Hotel. See all three locations on one tour that reveals fascinating details about historical events, and rumors of murder and mayhem in Chicago.
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Chicago Lakeside Architecture Tour

• 8 reviews
• Get views of Chicago's famous architecture from the deck of a boat during this 75-minute sailing excursion. Learn about the people, plans, and persistence that shaped Chicago's architecture along the shoreline. Hear about the city's historical maritime roots to modern science and technology through your guide's commentary while taking advantage of great photo ops. Choose between an afternoon or early evening departure and relax as you enjoy the sights. 
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Scenic Chicago North Side Tour and 360 CHICAGO Observation Deck

• Discover the sights of North Chicago on a 2-hour group walking tour. Offered in the morning and afternoon, select a start time that fits with your schedule. Follow your guide to Millennium Park, Lake Michigan, and more. Feel free to pause for photos and ask questions whenever you like. You also get free admission to the 360 Chicago Observation Deck, which you can use at anytime until 10:30pm.
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Auditorium Theatre Historic Tour

• 1 review
• Get an insider’s look at Chicago’s architectural heritage during this 60-minute tour of Auditorium Theatre, a National Historic Landmark. Learn about the history of this 126-year old performance venue as you gaze in awe at the 24-karat gold-leafed ceiling arches, intricate wall mosaics, and painstakingly-restored stencil patterns. You’ll also learn about the numerous concerts, plays, operas, political conventions, and more that have graced its stage.
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Chicago Lakefront and Museum Campus Segway Tour

• 10 reviews
• Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths and rose gardens of Grant Park to famous Buckingham Fountain. Then travel along the banks of Lake Michigan, past Monroe Harbor to the Museum Campus for a breathtaking view of the city’s iconic skyline. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
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Haunted Evening Chicago Pub Tour

• 1 review
• Enjoy a memorable Chicago experience with this haunted pub tour. Your costumed guide, dresses as a Flapper or 1920s Gangster, will lead you on a mile-long, 2.5-hour journey while telling spooky stories of forgotten cemeteries, lingering spirits, and more. Stop at three different bars for drinks (at own expense) as you learn the secret tales behind Chicago’s haunted past.
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Walking Tour of Lincoln Park in Chicago

• 1 review
• Step off the tourists’ path to visit Lincoln Park, a neighborhood beloved by Chicagoans for its stately homes, historic zoo, and stunning green areas. Your tour begins at the charming Children’s Fountain and continues to unexpected sites like the shrine of the first American saint. As your local guide leads you through the city’s largest park, you’ll marvel at the wild feel of this neighborhood just north of downtown Chicago.
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Evening Chicago Ghost Tour by Bus

• 3 reviews
• Calling all fans of the paranormal, this 1.5-hour ghost bus tour of Chicago takes you into the city’s darkest recesses to reveal its dark past. Travel with ease between locations of reputed haunting and listen to spine-chilling tales delivered by a historian guide. The City Cemetery, the Levee Vice district, and Prairie Avenue all feature on the itinerary, in addition to the site of the notorious St. Valentine’s Day massacre.
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Chicago Architecture Walking Tour: Historical Masterpieces of the Loop

• 2 reviews
• Learn the stories behind the skyscrapers on a 2-hour walking tour of Chicago’s architectural history and highlights. Follow your knowledgeable guide through the Loop district,  take in the city’s most important buildings and get a new perspective on the Second City skyline. Enjoy the bustling streets of this diverse, vibrant neighborhood as you compare buildings across time and contrast works by the same architect. You’ll never look at Chicago’s iconic building the same way again.
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Chicago Segway Art and Architectural Tour

• 8 reviews
• Explore the art and architectural highlights of Chicago on a Segway during this 2-hour guided tour. This family-friendly tour takes visitors by the outdoor sculptures, landmark buildings and iconic skyline of the city. Accompanied by educational and informative commentary, this city tour saves you from hours of walking and lets you see all of Chicago's top art and architectural attractions in one tour.
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Intro to Hyde Park

• 1 review
• Go beyond the Chicago Loop with this in-depth walking tour of the Windy City’s historic Hyde Park area. Hang out in the former neighborhood of the Obamas as you visit the Chicago home of the ‘First Family,’ check out a landmarked building by Frank Lloyd Wright and explore the campus of the University of Chicago. It’s perfect introduction to this charming South Side neighborhood.
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Chicago Land and River Architecture Tour: Historic South Side

• This tour will take you past all the sights of Chicago’s Historic South Side. You will head south out of the Loop down Michigan Avenue past Art Institute of Chicago, the starting point of historic Route 66, Grant Park and the site of Chess Records. Your journey will continue along Lake Michigan on South Lake Shore Drive. Travelling on you will see President Obama’s home, University of Chicago and Jackson Park and the Museum of Science & Industry. The return trip will take you through Museum Campus and past Buckingham Fountain  You will also enjoy a 90-minute Architecture River Cruise
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