Chicago Loop
Tours

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Our most recommended Chicago Loop Tours

Chicago River: 1.5-Hour Guided Architecture Cruise

1. Chicago River: 1.5-Hour Guided Architecture Cruise

Experience more of Chicago by boat than on any other architectural cruise. See architectural highlights and enjoy an open-air deck or climate-controlled interior as you travel the main River and its north and south branches. View all of Chicago's architectural highlights during this comprehensive sightseeing tour. Be entertained by the expert and friendly tour guides as they explain the 130 year-long history behind the skyline, while bartenders and staff keep you comfortable with refreshments.  Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. The tour starts at the Michigan Avenue (DuSable) bridge and goes up the main branch of the Chicago River past Wolf Point. It then cruises along the north and south branches of the river, before heading back past the Chicago Riverwalk towards Lake Michigan. On the way, learn about ornate, historic early skyscrapers like the Wrigley Building and the Tribune Tower, the imposing art deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building. Don't miss the circular Marina City Towers, the majestic Willis Tower (formerly the Sears Tower and the tallest building in Chicago) the soaring AON Center, and more modernist structures like Aqua, Trump Tower, Nuveen, and the new Vista Tower. During your cruise, have the opportunity to enjoy a full-service cash bar featuring authentic Chicago products, including local beer and spirits, and Garrett’s Popcorn. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

Chicago: Mob and Crime Bus Tour

2. Chicago: Mob and Crime Bus Tour

Experience Chicago’s underworld of criminals and gangsters on a luxury bus tour. Find out how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the city. Ride comfortably in luxury, on a climate-controlled bus, as you see famous Chicago crime scenes that range from the 19th century through modern times. Unlike Chicago walking tours, this Mob and Crime Tour isn’t affected by the Windy City weather. Learn from a local expert tour guide giving interactive live commentary about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, Terrible Tommy O'Connor, H. H. Holmes, the Chicago Black Sox, Leopold and Loeb, bank heists, Cap George Streeter, and more. Grab your camera for a drive-by shooting of the historic criminal courthouse, a Chicago architectural landmark where some of Chicago's most notorious cases were tried. You'll also view historic video footage, receive an informative pamphlet with photos, and can even take part in a crime quiz. Stake out crime scenes like the Biograph Theatre, Holy Name Cathedral, Clark Street Bridge, and other Chicago landmarks. See the site of the St. Valentine's Day Massacre, one of Chicago's most notorious murder scenes. Get off the bus and walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnificent Mile neighborhoods.

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

3. Chicago: Gangsters and Ghosts 2-Hour Walking Tour

See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with interesting stories hidden behind each turn. Embark along the Chicago Loop, known as the vice district during the 1920s and 30s. See the places where gangsters such as Al Capone used to party, make deals, and carry out business. Visit haunted locations and old crime scenes led by historians. Stop at the Congress Hotel, Death Alley, and the Palmer House. Enjoy a refreshment along with way, with frequent stops and a restroom break.

Chicago Crimes Night Tour

4. Chicago Crimes Night Tour

Uncover how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the Windy City. Ride in luxury on a climate-controlled bus, as you explore famous Chicago crime scenes ranging from the 19th century through to modern times. Learn about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, The Lady in Red, Captain George Streeter, Frank "The Enforcer" Nitti, Bugs Moran, Johnny Torrio and more. Grab your camera for a drive-by shooting of historic and architectural landmarks, and stake out crime scenes like the Biograph Theatre, Holy Name Cathedral and St. Valentine's Day Massacre, one of Chicago's most notorious murder sites. Walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnificent Mile neighborhoods.

Chicago Food Tasting: 2.5-Hour Guided Walking Tour

5. Chicago Food Tasting: 2.5-Hour Guided Walking Tour

Combine an enjoyable walk around Chicago's downtown to see some of the city’s top sites with stops to sample some of the city’s famous tastes. On this 2.5-hour guided walk, you'll get to taste the foods Chicago is best known for doing right. Enjoy deep-dish pizza, the original Italian pastries, Chicago-style hot dog, and a classic Italian beef sandwich. Enjoy a VIP craft beer sample for an additional fee. Along the way, you’ll see some of Chicago's most iconic spots including Millennium Park, the Chicago Riverwalk, the Art Institute, and the famous Bean. By the end of the tour, your stomach will be full of delicious food and your head will be full of fascinating knowledge about Chicago. During the colder months, the tour makes use of the unique underground Pedway system that connects much of downtown and keeps you warm and cozy. On warmer days, you’ll walk at street level to enjoy the large promenades of the loop. The leisurely walking pace is suitable for people of all fitness levels.

Chicago City Mini Bus Tour with Optional Architecture Cruise

6. Chicago City Mini Bus Tour with Optional Architecture Cruise

After your hotel pick-up from most downtown Chicago hotels, board your climate-controlled minibus with a small group of twelve people or less. Enjoy the sightseeing tour which has won Chicago's "Concierge Preferred" award several years running.  Your tour begins in the heart of downtown Chicago, at The Loop.  Here you'll see incredible architecture, including the world's first skyscrapers.  You'll even go inside one that features a beautiful lobby designed by Frank Lloyd Wright.  The stop also includes views of The Chicago Board of Trade and the Willis (Sears) Tower. After The Loop, you'll tour through Grant Park, which is known as the city's front yard. The centerpiece of the park is the Buckingham Fountain (operational May to October).  Museum Campus is up next, with three museums, Soldier Field and the most spectacular skyline views in the city.  After a ten minute photo stop, you'll travel around Millennium Park, featuring The Bean, before heading up north along Wacker Drive, which parallels the Chicago River. You'll arrive in the fancy Gold Coast nightlife area and residential neighbourhood - one particularly interesting sight here is the original Playboy Mansion. Then you'll take a trip through part of Lincoln Park, and end the tour by zipping along Lake Shore Drive, past beaches and old mansions as we get you back to or near your hotel or parking place. For those wanting the ultimate Chicago experience, add on the option of the world-famous architecture cruise of Chicago. After your 2-hour minibus tour and a short break, climb aboard a state-of-the-art cruise vessel for a 75-minute cruise of all three branches of the Chicago River. Marvel at the architecture that has made the city so legendary. Gain insights into the buildings and engineering of a city that gave birth to the skyscraper and is the spiritual home of modern American architecture. An expert guide will lead you down the Chicago River to uncover hidden gems, as well the city’s most renowned landmarks, such as the John Hancock building and more.  

Chicago: Treasures of the Golden Age Walking Tour

7. Chicago: Treasures of the Golden Age Walking Tour

This Historic Treasures of Chicago tour covers the most significant historic architectural landmarks in Chicago’s Loop. Your expert guide, trained by the Chicago Architecture Center, will focus on great cultural buildings from the late 19th and early 20th centuries, which harkened back to earlier time periods and were designed in revival styles such as Beaux Arts, neo-Georgian and neo-Gothic. Marvel at exteriors and interiors of dazzling beauty and startling originality, and get a glimpse inside some of the city's most beloved buildings.    The highlights of this walking tour will include the Chicago Cultural Center, home to the world's largest Tiffany dome; the iconic Marshall Field's department store, now Macy's on State; and the Palmer House, a beautifully restored hotel from the 1920s. 

Chicago: Underground Pedway & Downtown Secrets Walking Tour

8. Chicago: Underground Pedway & Downtown Secrets Walking Tour

Come experience Chicago's famous "Pedway" – the mysterious underground tunnels downtown that keeps us all warm & dry in bad weather. Wandering the Pedway, through hidden corridors of stained glass and even underground swimming pools, you'll access interiors that seem to come up out of nowhere. In the first part of our 2-hour walk, on weekdays, you'll see beautiful and historic government building interiors, learning not only about the design and history of the buildings, but also about the movies filmed there. On weekends, as government buildings are closed, we instead explore a couple stunning interiors with stained glass mosaics that will leave you awe-struck. You'll walk under full blocks of buildings, up and down staircases, accessing these buildings through the Pedway's secret passages. In the second part of our walk, you'll discover some of the other "secrets of the Loop" hidden in plain sight. What is the meaning behind "The Bean"? What is the significance of Chicago and Route 66? How can someone walk right by a garden and not even SEE it -- or walk by a building and not see it, for that matter? You'll find so many secrets, packed into a leisurely 2-hour walk with your expert Chicago guide. Ending with a fabulous “secret” interior near the Art Institute, you’ll be in the perfect central spot for continuing your exploration of downtown Chicago on your own after the tour!

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

9. Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Spend an evening visiting the Chicago speakeasies that have been open since the Prohibition Era in the 1920s, many preserved in their original conditions. With your own private group, enter by way of secret entrances and enjoy the same cocktails ordered by infamous Chicago gangsters and bank robbers at these venues nearly a century ago. Relive the glamor of the 1920s while listening to stories of the rampant racketeering and bootlegging of the era.   Alcohol is available for purchase at the three to four different speakeasy stops. Your private tour guide will make Prohibition Era drink recommendations and tell you the stories behind them. Travel around with your young, professional guide and be chauffeured in luxury transportation, ranging from a luxury SUV to a full-sized luxury motor coach.

Chicago: Secret Food Tour

10. Chicago: Secret Food Tour

Sample the culinary delights of Chicago with the help of a fun and enthusiastic foodie guide. Be amazed by the city's eclectic mix of architecture and public art along the way. Taste delicious bites as you explore the city's central Loop district for 3 hours. Get better acquainted with what sets this friendly Midwest metropolis apart from other destinations and get a great insight into the art, architecture and everyday life in the city. Benefit from your guide's local knowledge and get tips to help you sightsee and explore the food and dining scene some more in your own time.

Frequently asked questions about Chicago Loop Tours

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Other Sightseeing Options in Chicago Loop

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What people are saying about Chicago Loop

Overall rating

4.5 / 5

based on 740 reviews

Frankie was an excellent guide and gave us a great tour. Lots of little gems around the city hidden in plain sight. Highly recommended!

conner was a great, knowledgeable guide. we enjoyed our tiur very much.

Excellent scenic views of Chicago skyscrapers on a peaceful boat ride!!

Andrea did an amazing job to make it entertaining yet informative.

Departure is on time Rain or Shine Great Bartender Great Captain