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1. Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop

480+ reviews


Explore the hidden gems of Chicago’s Loop district with a 2-hour walking tour that showcases the best of the lively neighborhood’s indoor spaces. Discover the beauty of the area’s stunningly designed interiors as you walk along a specially-designed route with a knowledgeable guide. While visiting a side of Chicago that is off the beaten path, learn about the city’s architecture, art, and history, and gain a local’s perspective on the Windy City.

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2. Chicago Walking Tour: A Walk Through Time

90+ reviews


Experience a journey through architectural history on this walking tour that takes you through Chicago’s most renowned buildings in a chronological order. Led by a guide, you can simply focus on enjoying the walk and listening to the detailed commentary on the history of Chicago’s architecture. Learn about the significance of each building in the architectural world and leave the tour with new knowledge, without the need to fret over maps or directions.
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3. Chicago Architecture & Highlights with Local Treat

60+ reviews


Experience the best of Chicago on this tour guided by a local expert! The Windy City offers plenty of highlights such as incredible architecture, impressive public art, a vibrant downtown, and much more. Discover some of the must-see places in downtown Chicago, and admire the famous towering architecture that the city is known for. Learn about the history of some of Chicago’s most iconic buildings, take in views of the Chicago River (weather permitting) and savor a delicious local snack. Your guide will also reveal some lesser-known but local favorite spots, giving you an authentic feel for what makes Chicago unique.
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4. Chicago Architecture Walking Tour: The Underground Pedway & Secrets of the Loop

50+ reviews


Discover the lesser-known side of Chicago on a 2-hour guided walking tour of The Loop, an area brimming with rich history, architectural gems, and colorful personalities. Your local guide will lead you along the sidewalk and help you discover the overlooked details and untold stories that even long-time residents may have missed. Experience the city on an intimate level as you explore its little treasures, while getting an insider’s look at life in the Second City.
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5. Chicago Walking Tour: Historic Skyscrapers

50+ reviews


Uncover the history and beauty of the Loop’s iconic architecture with this 2-hour guided walking tour led by an expert guide from the Chicago Architecture Foundation. Learn about the origins of the Chicago School of Architecture as you visit some of the city’s earliest skyscrapers, dating back to the late 19th and early 20th centuries. This sophisticated and informative tour is a must-do for those interested in history and architecture.
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6. Chicago Loop Walking Tour

45+ reviews


Experience the heart of Chicago on this 2-hour walking tour of the Loop, led by a local guide. You’ll start at the Chicago Cultural Center, and walk through the city’s downtown area, visiting the elevated “L” train, buildings by Burnham and Sullivan, bustling commercial centers and lesser-known peaceful corners of this dynamic neighborhood. With a deeper understanding of the city’s rich history and architecture by the end of the tour.
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7. Underground Chicago PLUS RATS Tour

20+ reviews


Explore the lesser-known and often overlooked side of Chicago’s downtown on this one-of-a-kind tour, the Underground Chicago (Plus Rats!) tour. The city’s downtown is home to hidden streets, train stations, and pedestrian tunnels, which are filled with innovative and interesting design features that you won’t find anywhere else. Many of these features date back over a century, and a special focus on one of the city’s most interesting inhabitants, the rats. These fascinating creatures have a lot in common with Chicago – they’re scrappy, adaptable, resilient, and their fates are thoroughly interconnected. This fun and unique tour will take you through an underground labyrinth of this infrastructure and urban wildlife, showcasing features and stories that are rarely noticed, and providing you with lots of surprising rat facts that will give you a new appreciation for these critters.
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8. Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

15+ reviews


Take a journey through Chicago’s history and public transportation on this interactive tour of the city’s iconic “L” or elevated train. This tour will be conducted in the morning, which is led by an expert guide, and limited to a small group for a personal experience. Starting in the Loop neighborhood, you’ll learn about the railway’s history as you ride it like a local. Along the way, you’ll also get a chance to view Chicago landmarks such as the Willis Tower, while gaining insights into the city’s architectural history.
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