Small Group Chicago
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Tours
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Featured Attractions
Featured Small Group Chicago Tours
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Chicago
Chicago River 45-Minute Architecture Tour from Magnificent Mile
Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural her…
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Chicago
Small-Group Sightseeing Boat Tour in Chicago
The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights around the local waterways including the Navy Pier, Soldi…
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Chicago
Chicago Landmarks & Museum Campus Small Group Segway Tour
Looking for fun things to do in Chicago? Explore the city with one of our professional guides on a scenic 6-7 mile tour. Begin your adventure by gliding through the fragrant garden paths of Grant Park, where you'll admir…
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Chicago
Chicago Lake and River Architecture Tour
An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than …
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Chicago
Chicago River 90-Minute Architecture Tour
Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute…
Chicago
Chicago Architecture Center River Cruise aboard First Lady
The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert doc…
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Chicago
360 CHICAGO Observation Deck Admission
The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City in the former John Hancock Building, 360 Chicago provides commanding views of Lake Michigan and Chicago’s to…
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Chicago
Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline
Discover the architectural soul of Chicago on a thoughtfully curated half-day city tour. Travel through the city’s most influential districts, from historic riverfront landmarks to groundbreaking modern skyscrapers. Expl…
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Chicago
Flyover in Chicago
The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover Chicago from a whole new perspective, as Flyover transports…
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Chicago
Chicago Sightseeing River and Lake Cruise
Our popular 90-minute daytime river and lake sightseeing tour delights family members of all ages with incredible views of Chicago's world-renowned buildings and stunning skyline. Lively, knowledgeable tour guides bring …
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Chicago
Skydeck - Willis Tower Admission
Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest building in the world -- the Skydeck offers spectacular sweeping …
Free Cancellation
Chicago
City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River
Sail along the magnificent skyline on our Premier Plus Chicago Brunch Cruise. A chef-curated menu of plated brunch specials will delight your palate while unparalleled panoramas of the city’s iconic architecture are marv…
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Chicago
Chicago By Night River and Lake Cruise
Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night! Enjoy breathtaking views of the dramatic skyscrapers and Buckingham Fountain's spectacular light display. Hear lively com…
Chicago
Chicago CityPASS®
Experience 5 top attractions and save up to 50% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax and enjoy your memories in the making. With 9 days to use your tickets,…
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Chicago
Frank Lloyd Wright Robie House Admission
The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture. This Prairie style masterpiece is now a UNESCO World Heritage Si…
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Chicago
Chicago River 90-Minute Architecture Boat Tour
Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional guide which leads passengers down the Chicago River to di…
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Chicago
Chicago Architecture Tour: Underground Pedway and the Loop
This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall narrative of Chicago. On this tour, we will explore the famo…
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Chicago
Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour
Discover Chicago’s dark side on a chilling 2-hour walking tour. Strolling just under 2 miles at an easy pace, we reveal stories of gangsters, tragedies, and restless spirits hidden behind the city’s glamorous façade. Hea…
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Chicago
Chicago Walking Tour: Historic Treasures of Chicago
Learn about the great architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of Chicago’s the most memorable buildings, many of which are featured on this…
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Chicago
Lake Michigan Sunset Cruise in Chicago
The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago River, through the Chicago Lock and out onto Lake Michigan…
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Chicago
Chicago Walking Tour: Must-See Chicago
Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Art Institute of Chicago, Willis (Sears) Tower and …
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Chicago
2-Hour Guided Segway Tour of Chicago
2 hours of being a kid again!!! Take a Segway tour with us and discover how beautiful Chicago truly is. Ride through some of Chicago's most popular destinations with an experienced guide. We will glide through scenic and…
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Chicago
Chicago Loop Food Tour: Taste the Most Iconic Local Eats
Join a local guide for the ultimate foodie adventure in Chicago’s historic Loop, tasting classics like deep‑dish pizza and Chicago‑style hot dogs while discovering insider stories behind the city’s rich food culture.…
Free Cancellation
Chicago
Chicago's Chinatown Food and Walking Tour
Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours have ranked Top 10 in America by USA Today & Top 20 in the …