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
16 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.
Learn about Chicago's history and architecture from a local expert as you enter historic Chicago Loop buildings and explore city streets and the underground Pedway on a guided walking tour.
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.
Uncover the chilling history of Chicago’s gangsters and ghosts on a thrilling guided walking tour, including a late-night Halloween special. Dive into the dark, eerie secrets of the Chicago Loop!
Experience the best of Chicago’s city center as you stroll past celebrated landmarks, impressive architecture, and cultural attractions while learning the stories that shaped the Windy City.
Solve a famous opera singer's 1923 murder by following clues and cracking puzzles through the Chicago Loop. Walk city streets from The Art Institute of Chicago to The Sullivan Center.
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.
