Immerse yourself in the electric energy of the Chicago Loop, the ultimate urban destination for sightseeing and culture. Discover iconic architecture, world-class museums, and legendary food tours through our curated selection of guided walking tours and historical adventures. Whether you are exploring historic landmarks or tasting the city's best pizza, our top-rated experiences offer an authentic taste of Chicago life. From vibrant cultural hubs to breathtaking skyline views, book your Chicago Loop adventure today and uncover the hidden gems of the Windy City with ease.
$51–$80 typical
Median price is $61, with a spread of $33–$91
4.84★ average
Based on 2,411 pooled reviews
Walking & Cultural
75% of options are walking tours and cultural themes
2 hours median
Typical duration ranges from 1.8 to 3.7 hours
Historical tours
Average 4.87★ at $49 per person
Eco-friendly options
38% of tours are tagged eco-friendly
10 Products
Embark on a history-based guided walking tour and discover the stories of Chicago’s gangsters and ghosts. Learn about the city’s darker side and creepy past as you explore the Chicago Loop district.
Enjoy Chicago’s only bus guided neighborhood pizza tour. Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza. Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias. In just ...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Taste Chicago’s iconic foods on this Loop District tour! Deep dish pizza, Italian beef, gourmet popcorn and more tastings, plus our delicious Secret Dish!
Short on time? Discover Chicago’s food, stories, and local life on this small-group Loop walk. Perfect for first-time visitors with iconic bites and insider tips in 2 hours.
Explore Chicago’s Loop neighborhood on a guided walking tour. Discover the iconic “L” train, admire historic buildings, and uncover hidden gems and public artworks.
Discover the hidden architectural gems of downtown Chicago. Explore carefully selected buildings in the Loop that showcase architectural brilliance and witness over two centuries of unique interiors with expert guidance.
Step back in time to the roaring 20s with a thrilling tour of Chicago's most infamous historic bars. Hop aboard a sleek coach and be whisked away to the hidden haunts of Old Town, Wicker Park and the Chicago Loop, where the liquor flowed like a river and jazz was king. Led by a knowledgeable guide, ...
Starting at the Chicago Architecture Center (CAC), this tour gives you an overview of many of the must-see buildings and landmarks in the City of Chicago. Led by an expert guide who's equal parts storyteller and educator, you will get a fantastic introduction to the city’s wide variety of architectu...
Free cancellation up to 24 hours before the start time.”
Step into 1920s Chicago and solve a thrilling murder mystery in the heart of the Chicago Loop. Follow clues, crack puzzles, and uncover who killed the famous opera singer.
Discover the heart of Chicago on a private walking tour through its most iconic landmarks, from Daley Plaza to Millennium Park, exploring art, architecture, history, and the city’s vibrant atmosphere.
Landmarks travelers visit on the same route as Chicago Loop.
