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Top Chicago Cultural Tours

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Frank Lloyd Wright by Bus Tour from Chicago

Take a deep dive in to Frank Lloyd Wright's Prairie Style on this 4-hour architecture tour of Oak Park from Chicago. Listen to your guide's commentary during the trip, then take a walking tour of the Frank Lloyd Wright Historic District and a tour of the architect's home and studio.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
US$55.00
From  
US$55.00
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Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

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.
  • Duration: 2 hours
  • Duration: 2 hours
From  
US$28.00
From  
US$28.00
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Private Al Capone Gangster Tour in Chicago

Chicago’s mob history has long been immortalized in popular media. Embark on this Chicago Gangster Tour to learn the true story. With an expert historian as your guide, you’ll visit notorious hangouts of John Dillinger, The Untouchables, and the legendary Al Capone. You’ll stop at former speakeasies, historic hotels, and epic crime sites like that of the Saint Valentine’s Day Massacre.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$660.00
From  
US$660.00
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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.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$89.95
From  
US$89.95
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Chicago Lakefront and Museum Campus Segway Tour

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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$68.67
From  
US$68.67
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NEW TO VIATOR

The Original Surf & Turf Tour: A Combination Boat AND Walking Tour!

Our super unique combination of "must see" Chicago sites in one tour — Chicago by boat, by train, and on foot! On this brand new tour route that has been a long-time wish of company founder and award-winning tour guide, Hillary, you will be able to experience Chicago in the best ways possible: by boat on the Chicago River, by “L” from one of Chicago’s fascinating Chinatown neighborhood, and on foot through the center of the city. Inside Chicago Walking Tours calls these new tours “Surf & Turf” tours because you don’t have to worry about choosing a boat tour OR a walking tour: we’re finally giving you both in ONE tour! Come on our newest, most exciting, and most unique tour yet! Let Inside Chicago Walking Tours put their expertise and know-how about the best ways to experience Chicago to use for you, and join us in exploring the best parts of Chicago by boat, by train, and on foot! No need to purchase extra tickets for the boat and train — they’re provided in your ticket price!
  • Duration: 120 to 150 minutes
  • Free Cancellation
  • Duration: 120 to 150 minutes
  • Free Cancellation
From  
US$45.00
From  
US$45.00
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Chicago Walking Tour: Modern Architecture

Embark on a walking tour of Chicago's more-recent architecture heritage with a 2-hour stroll highlighting the city's modern, postmodern, and international structures. Especially known for its architectural originality, Chi-town boasts everything from the elegant metal and glass tower of One South Dearborn to the Harold Washington Library, with its Beaux-Arts inspired exterior. Your guide will highlight these and other unique buildings, relaying background on their individual histories and construction en route.
  • Duration: 1 hour 45 minutes
  • Free Cancellation
  • Duration: 1 hour 45 minutes
  • Free Cancellation
From  
US$26.00
From  
US$26.00
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NEW TO VIATOR

Chicago Neighborhoods by L Train and on Foot: Green Line South

Explore Chicago's neighborhoods, culture and history via the elevated train system, with some walking, stories and small bites along the way. This unique Chicago tour begins with an exploration and a bite at one of the city’s newly revitalized spaces: The beautiful Chicago Athletic Association Hotel. Before boarding the train, we’ll visit a few historic and cultural stops in the Loop then make our way to the Cermak-McCormick Place Station.Upon arrival in the Prairie District, we’ll walk to a number of historic sites such as the former Chess Records, the oldest house in the city, the historic Second Presbyterian Church and the Glessner House. To top it off, we’ll finish with some small bites and a drink at Fatpour Tap Works. Following the tour, your guide will be available to assist with directions and your return trip to the Loop.
  • Duration: 4 hours
  • Duration: 4 hours
From  
US$70.00
From  
US$70.00
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Chicago Walking Tour: Art Deco Skyscrapers

Admire the incredible façades and intricate interiors of the Windy City's 1920s art deco and art moderne buildings during this architecture walking tour of Chicago. Uncover the history of Chicago art deco architectural along with the city's influential role in the development of this iconic artistic style, as you get an up close and personal look at its wealth of gorgeous period buildings. This art deco Chicago walking tour also includes a certified guide.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
US$26.00
From  
US$26.00
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NEW TO VIATOR

The Chicago Tour

This tour is an overview of some of Chicago's most fascinating neighborhoods, history, architecture, and foods. We will take you beyond the downtown loop to explore some of the great neighborhoods that make up this amazing and diverse city. Did you know that Chicago is home to 77 distinct neighborhoods? Each one has their own personality and vibe that make it worth exploring. The Chicago Tour will help you see the city without worrying about the logistics or the effort of planning and will explore the Loop, Chinatown, Pilsen, and the West Loop. Be prepared to walk a lot as we will explore by foot and use the city public transportation to connect us to each neighborhood. Together we will see the city by going off the beaten path for a more authentic experience. Each tour will include all food and drinks (listed in itinerary below) and an unlimited public transit day pass. So, after the tour wraps up, you have the ability to go back and explore more of the city!
  • Duration: 4 hours
  • Duration: 4 hours
From  
US$99.00
From  
US$99.00
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NEW TO VIATOR

The Entrepreneurs of Chicago

Learn about the entrepreneurs who built Chicago on this walking tour. We'll see the locations around the Loop where these titans of industry made their mark, turning what was once a small military outpost into one of the most innovative cities of the century. Focusing on the entrepreneurs during the time between Chicago becoming a city (1833) to the World's Fair (1893), you'll hear some names you recognize, and possibly some you don't. During this 90 minute tour, you'll get to know several of Chicago's greatest entrepreneurs:What were their backgrounds? What were their struggles? What strategies did they use to beat the competition? How did they build their empires? And what advice would they give?Get ready to walk ~2.5 miles of Chicago's downtown streets where you will see exactly where these 19th-century industrialists built their fortunes.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
US$30.00
From  
US$30.00
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Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$30.00
From  
US$30.00
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Chicago Architectural Aficionados Bus Tour

Get an overview of Chicago's famous architectural history on this 3.5-hour bus tour. Learn about the city's history through your guide's history, from its founding to the present. Stops include the Loop, Mies van der Rohe's IIT campus, Frank Lloyd Wright's Robie House, and the Museum Campus.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$55.00
From  
US$55.00
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Chicago Segway Art and Architectural Tour

Explore the art and architectural highlights of Chicago on a Segway during this 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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$70.40
From  
US$70.40
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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.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$51.95
From  
US$51.95
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Walking Tour of Lincoln Park in Chicago

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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$30.00
From  
US$30.00
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Chicago Land and River Architecture Tour: Historic South Side

See the architecture of Chicago's South Side by both land and on a Chicago River boat tour. Traveling south of the Loop along Michigan Avenue and South Lake Shore Drive, you'll pass by sights such as the Art Institute of Chicago, University of Chicago, Jackson Park, the Museum of Science and Industry, Museum Campus, Buckingham Fountain, and former President Obama's home.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$73.95
From  
US$73.95
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Historic Chicago South Side Tour and 360 CHICAGO Observation Deck

Discover the historical sights of South Chicago on a 2-hour group walking tour. Select the morning or afternoon start time, depending on your preference. Follow your guide to Grant Park, Buckingham Fountain, Obama's House, and other sites that define the historical South Side. Pause for photos and ask questions at any time. You also get a free ticket to the 360 Chicago Observation Deck, which you can use at anytime until 10:30pm.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$51.95
From  
US$51.95
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Chicago Chinatown History & Culture Tour

Spend some time in Chicago’s vibrant Chinatown, learning the history of the buildings and people who formed it. Visit landmarks like Nine Dragon Wall, the Chinese Buddhist Temple, St. Therese Catholic Church, Chinese Zodiac Park, and more. This tour is a great introduction to Chinatown. Make a note of all the interesting stores and bakeries you pass so you can go back on your own after the tour.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
US$15.00
From  
US$15.00
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CHICAGO ARCHITECTURE TOUR

Surround yourself in the Windy City's architectural gems on a 2-hour walking tour. Follow your guide past noteworthy landmarks and lesser known gems. Then visit the Chicago Cultural Center, also known as The People’s Palace, and marvel at the Randolph Street entrance, Grand Army of the Republic Memorial, and more. Beginning at the Clark Street Bridge, the tour concludes next to Millennium Park where you can continue your day of sightseeing.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$25.00
From  
US$25.00
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The Rolls-Royce Experience in Chicago

Spend an hour in the lap of luxury as you tour Chicago in a chauffeured Rolls Royce Ghost. Explore Different areas starting in the lower west side neighborhood of Pilsen. Then move on to Little Italy, before reaching the tall buildings along Lakeshore Drive. Leave the driving and navigating to the experts and relax in style as your guide points out significant sights and gives you some Chicago history.
  • Duration: 1 to 2 hours
  • Duration: 1 to 2 hours
From  
US$420.00
From  
US$420.00
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Land and River Architecture Tour of Chicago's Scenic North Side

Discover Chicago’s iconic architectural gems from every angle on a 3.5-hour tour of the North Side. Divided between land and water, the comprehensive tour enables you to cover a huge area of the city without getting worn out. Travel comfortably by coach or trolley to Fort Dearborn, Wrigley Building, and more. Afterwards, see the Windy City's famous skyscrapers, bridges, and historical sites on a 90-minute cruise down Chicago River.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$73.95
From  
US$73.95
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NEW TO VIATOR

Chicago Deluxe Motor Coach Tour

This is a very thorough and relaxing city highlights tour! We pick up at three downtown hotels before beginning our adventure at 875 N. Michigan, the former John Hancock Center. We’ll have a photo-stop at the home of the Cubs, the legendary Wrigley Field. We’ll then take Lake Shore Drive to the home of the Bears, the historic Soldier Field. We’ll make a photo-stop at the Museum Campus for the best view of the lake and skyline. Passing by the White Sox stadium, your driver and tour guide will take you through Chinatown, Greektown, and other fun areas. We’ll show you the architectural masterpieces of the Loop on the way to our origin at the top of the Magnificent Mile and the destination hotels.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$55.00
From  
US$55.00
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Urban Art 101 in Chicago

Learn about the evolution of urban art in Chicago on this tour that introduces you to works by local and visiting artists. You'll explore the Logan Square neighborhood to see its graffiti and other street art, hearing about the history and future of the art medium along the way.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$20.00
From  
US$20.00
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