

Chicago Loop Tours and Activities
2,651 Reviews
Chicago’s central business district, the Loop, is home to many of the city’s most recognizable landmarks, from museums and skyscrapers to parks and outdoor sculptures. Renowned for highlights like Grant Park, City Hall, and the Willis Tower, the Loop attracts both locals and visitors with its culture and entertainment offerings.
Chicago, Illinois
Tours and Activities to Experience Chicago Loop
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Gangsters and Ghosts Tour in Chicago
1269
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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From
$27.00
From
$27.00
Face masks required for guides in public areas
Social distancing enforced throughout experience
Regular temperature checks for staff
Learn More

Chicago's West Side Foodie Ride Bike Tour
69
Taste food from around the world on this half-day cycling and tasting tour of Chicago. Follow your biking guide through the Chicago streets, stopping for views of Chicago’s famous architecture as well as bites like Polish pierogis, locally made chocolates, and Mexican tacos.
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From
$79.99
From
$79.99
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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Underground Donut Tour: Chicago's First Donut Tour
182
Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and vegan, gluten-, and nut-free options are also available.
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From
$30.00
From
$30.00
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
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Chicago Favorites Ultimate Food & Walking Tour
149
Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels.
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From
$62.99
From
$62.99
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Big Bus Chicago Hop-On Hop-Off Tour
701
Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while live commentary onboard gives you insight into the city's colorful history.
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From
$26.10
From
$26.10
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
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Chicago Loop Secret Food Tour with Private Tour Option
245
Explore Chicago's buzzing food scene with a small group on this small group walking tour. Stroll around the 'Loop', stopping at hidden gems and hearing tales of the city from your guide. Taste classic Chicago foods, from deep-dish pizza to dipped Italian beef sandwiches.
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From
$193.20
From
$193.20
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Private Al Capone Gangster Tour in Chicago
2
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.
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From
$330.00
Price varies by group size
From
$330.00
Price varies by group size
Face masks required for guides in public areas
Social distancing enforced throughout experience
Regular temperature checks for staff
Learn More

Behind-the-Scenes Tour of Historic Chicago Theatre
21
Tour the historic Chicago Theater, a must-see city landmark, with a guide providing in-depth commentary. You'll get the most out of your visit by traveling with a guide and get access to some areas of the theater that the public never sees. Learn about its architecture, history, and famous performers throughout the years.
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From
$18.00
From
$18.00

Private Chicago Instagram Walking Tour
1
Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a little bit of culture, some amazing architecture, & a ton of great photos then this is the tour for you.
The morning will start with meeting with your friendly local guide at the meeting point. From there your tour will begin as you start your day walking throughout Chicago and exploring the most famous locations in the city.
This half-day tour will be fully packed with famous landmarks, vintage architecture, secretly located spots and much much more!
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Full schedule
10:00 AM- Meet your Guide at the Grand Subway Station
10:10 AM- Walk along Magnificent Mile
10:20 AM- Stop at Wrigley Building & admire Tribune Tower
10:50 AM- Explore Pioneer Court
11:20 AM- Explore Millennium Park & see Cloud Gate
11:55 AM- Check out an Iconic fountain
12:20 AM- Chicago Riverwalk
1:00 PM- Explore Navy Pier
2:00 PM- Get dropped off by your guide at Millennium station
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From
$265.60
Price varies by group size
From
$265.60
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
Learn More

Private Secret Food Tour of Chicago
2
We are Chi-Town foodies of the first order, and we're so excited to share with you all the culinary delights this historic Midwestern city has to offer. There is so much to share about Chicago: historic enclaves, stunning architecture, an extensive collection of publicly displayed civic artwork, and a culinary style steeped in history. We will discover each facet of this unique city as we eat and explore Chicago's Loop District.
As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!
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From
$89.70
From
$89.70

Private Chicago Highlights Driving Tour
12
Get an insider’s look at the Windy City’s most iconic monuments during this 3-hour private tour. Travel through Chicago aboard a private vehicle as you discover some of the city’s top neighborhoods, including the Loop, River North, the Magnificent Mile (along Michigan Avenue), Streeterville, the Gold Coast and much more. Your private driver-guide and vehicle, bottled water and round-trip hotel transport are all included.
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From
$190.00
Price varies by group size
From
$190.00
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
Learn More

Best of Chicago Tour Including a Deep-Dish Pizza
5
Tour Chicago's sights aboard a luxury coach and enjoy some Chicago-style deep-dish pizza on this 5.5-hour guided tour. Visit sites like the Hancock Tower, the Lincoln Park Conservatory and the Loop. Pass through neighborhoods such as Wrigleyville, Lincoln Park and Gold Coast. Top off your tour with a visit to one of Chicago's most popular pizza restaurants to sample the famous Chicago-style deep dish pizza.
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From
$74.95
From
$74.95
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience
Learn More

Chicago City Tour and Chicago River Cruise
90
See Chicago from a new perspective during this 4-hour combined bus and boat excursion covering some of the city's most iconic sights. First discover Windy City landmarks such as the skyscrapers of the Loop, Grant Park, Shedd Aquarium, Soldier Field and the former stomping grounds of President Obama during a narrated coach tour. Then take a Chicago cruise aboard your state-of-the-art yacht, enjoying a cruise of the Chicago River that provides a unique look at the city's architecture from the water. This half-day Chicago exploration also includes hotel pickup.
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From
$76.95
From
$76.95
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience
Learn More

Historic Chicago South Side Tour with Chicago Style Pizza
2
See the sights of Chicago's South Side on a tour that takes you south of the Loop along Michigan Avenue and South Lake Shore Drive. Pass by attractions such as the Art Institute of Chicago, Frank Lloyd Wright's Robie House, former President Obama's home, the University of Chicago, Jackson Park, the Museum of Science and Industry, Museum Campus, and Buckingham Fountain. Then head to Exchequer Restaurant and Pub for Chicago-style pizza.
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From
$52.95
From
$52.95
Transportation vehicles regularly sanitized
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Historic Chicago South Side Tour and 360 CHICAGO Observation Deck
3
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.
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From
$55.95
From
$55.95
Face masks required for travelers in public areas
Face masks required for guides in public areas
Social distancing enforced throughout experience
Learn More
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