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Top Chicago Tours, Sightseeing & Cruises

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68 results | All Chicago Tours

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Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-5
2190
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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  • 2 hours
  • Free Cancellation
From
$35.00
From
$35.00

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1146
Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$46.00
From
$46.00

Chicago in a Day: Food, History and Architecture Combo Tour

Chicago in a Day: Food, History and Architecture Combo Tour

star-5
166
An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.
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  • 5 hours
  • Free Cancellation
From
$104.00
From
$104.00

Chicago Night Crimes Bus Tour
Likely to Sell OutLikely to Sell Out

Chicago Night Crimes Bus Tour

star-5
118
Discover the ‘dark side’ of the Windy City thanks to this 2.5-hour, bus-based, nighttime crime history tour of Chicago. Explore the lives of notorious mobsters like Al Capone, Frank Nitti, Bugs Moran, and more as you explore infamous crime scenes like the St. Valentine’s Day Massacre, learn about ‘The Enforcer’s Safe,’ and stop by local watering holes.
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  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
From
$51.00
From
$51.00

Lonely Planet Experiences: River North Historical Food Tour

Lonely Planet Experiences: River North Historical Food Tour

star-5
14
Get to know the food offerings in River North on this small-group walking tour. As you explore, listen to in-depth commentary from your guide on the culinary history of Chicago and the culture of the River North neighborhood. With a small group of just 12 fellow food-lovers, you'll enjoy personalized attention and the chance to chat about your favorite tastings. Samples include the classic Italian beef, a Chicago-style hot dog, and the famous deep dish pizza.
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  • 2 hours
  • Free Cancellation
From
$60.96
From
$60.96

Chicago Lakefront and Museum Campus Small Group Tour

Chicago Lakefront and Museum Campus Small Group Tour

star-5
150
Experience Chicago like never before on this small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths to famous Buckingham Fountain. Then travel along the banks of Lake Michigan, past Monroe Harbor to the Museum Campus for a breathtaking view of the city’s iconic skyline. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
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  • 2 hours
  • Free Cancellation
From
$73.24
From
$73.24

Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop

Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop

star-5
301
See the overlooked highlights of Chicago’s Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city’s architecture, art and history while visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.
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  • 2 hours
  • Free Cancellation
From
$33.00
From
$33.00

2-Hour Chicago Lakefront and Museum Campus Segway Tour

2-Hour Chicago Lakefront and Museum Campus Segway Tour

star-5
177
Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and glide along the Chicago lakefront to view attractions such as Museum Campus, Shedd Aquarium, The Field Museum, and Soldier Field, homefield for the Chicago Bears.
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  • 2 hours
From
$73.24
From
$73.24

2-Hour Guided Segway Tour of Chicago

2-Hour Guided Segway Tour of Chicago

star-5
127
Enjoy an active and entertaining way to explore Chicago’s highlights with this small-group Segway tour. Meet your guide at a convenient location in downtown Chicago, get acquainted with your Segway before setting off, and then hit the road. You’ll discover top Windy City highlights, including Millennium Park, the Buckingham Fountain, the Museum Campus, and more, all while learning about the city’s history and insider facts from your guide.
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  • 2 hours
  • Free Cancellation
From
$65.00
From
$65.00

Private Custom City Tour in Chicago

Private Custom City Tour in Chicago

star-4
1
See Chicago the way you want to see it. This private tour is fully customizable to your specifications. Whether you are interested in the architecture and history, the art, the cool neighborhoods, or peaceful parks and happening beaches, this tour will cater to your tastes. Work with a guide to discover Chicago your way.
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  • 3 hours
  • Free Cancellation
From
$465.00
Price varies by group size
From
$465.00
Price varies by group size

Untouchable Tours Chicago's Original Gangster Tour

Untouchable Tours Chicago's Original Gangster Tour

star-4
77
Book in advance to take this popular tour that details the mob history of Chicago during the Prohibition Era (1920s-1930s). Learn about the exploits of gangsters like Capone, Dillinger, Moran, and others as you travel by minibus to sites like the Biograph Theater, Holy Name Cathedral, and St. Valentine's Day Massacre. Your guide adopts gangster attire and characteristics that add dramatic flair to the historical commentary.
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  • 1 hour 45 minutes
From
$45.00
From
$45.00

2-Hour Haunted Segway Tour of Chicago

2-Hour Haunted Segway Tour of Chicago

star-4.5
28
Glide through the city of Chicago by moonlight on this haunted Segway tour. Follow your costumed local guide as they show you the sites of some of the most gruesome murders and disasters in Chicago's colorful history. See Chicago's iconic landmarks lit up during the spookiest time of year and hear about the mysterious, haunted history of this storied city.
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  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58

Half-Day Small-Group Chicago Highlights Tour with Pick Up

Half-Day Small-Group Chicago Highlights Tour with Pick Up

star-4.5
15
This Tour is the quickest, best way to explore a place that you are visiting for the first time, we take you to all the hot spots in the city in less than a day. We take care of everything for you, from picking you up at your hotel, to making reservations, parking, helping you with photos, all the way to dropping you off back where you started. zero worries and 100 percent enjoyment.
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  • 4 hours 30 minutes
  • Free Cancellation
From
$198.00
From
$198.00

Chicago Walking Tour: Must-See Chicago

Chicago Walking Tour: Must-See Chicago

star-5
4
Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Art Institute of Chicago, Willis (Sears) Tower, the Chicago Theatre and more! Get a brief overview of more than a dozen buildings—as well as Chicago landmarks like Millennium Park, the Loop and the Chicago River—on this whirlwind tour. There are lots of photo opportunities along the way, so be sure to bring your camera!
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  • 1 hour 30 minutes
  • Free Cancellation
From
$30.00
From
$30.00

Private Al Capone Gangster Tour in Chicago

Private Al Capone Gangster Tour in Chicago

star-5
3
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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  • 3 hours
  • Free Cancellation
From
$482.00
Price varies by group size
From
$482.00
Price varies by group size

Offbeat Chicago Food Tour: Go Deeper Than Deep Dish

Offbeat Chicago Food Tour: Go Deeper Than Deep Dish

star-5
97
Savor the flavors of Chicago — the ‘City of Neighborhoods’ — on a guided, ethnic food tour. This 3.5-hour adventure explores two of Chicago's most diverse neighborhoods: Argyle and Andersonville on the city’s North Side. Sample seven distinctly different types of food, visit landmark locations and learn about the local history and culture.
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  • 3 hours
  • Free Cancellation
From
$70.00
From
$70.00

Chicago Walking Tour: Art Deco Skyscrapers

Chicago Walking Tour: Art Deco Skyscrapers

star-4.5
81
Admire the incredible façades and intricate interiors of the Windy City's 1920s art deco and art moderne buildings during this architecture walking tour of Chicago. Uncover the history of Chicago art deco architectural along with the city's influential role in the development of this iconic artistic style, as you get an up close and personal look at its wealth of gorgeous period buildings. This art deco Chicago walking tour also includes a certified guide.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$30.00
From
$30.00

Amazing Lakefront Segway Tour in Chicago

Amazing Lakefront Segway Tour in Chicago

star-4.5
67
Experience Chicago like never before on this guided, 2.5-hour, small-group Segway tour. Visit popular Grant Park and see famous Buckingham Fountain, with the Windy City skyline as the backdrop. Glide along the lakefront, taking in views of the Field Museum of Natural History, Shedd Aquarium, Soldier Field, Adler Planetarium and Michigan Avenue. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toe shoes.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$75.00
From
$75.00

Chicago Insider Segway Tour

Chicago Insider Segway Tour

star-5
48
Enjoy an introduction to Chicago’s highlights and history—on wheels. This small-group Segway tour offers a new, and zippy, way to explore. Meet your guide near Millennium Park, and begin with a personalized training session. Once you’re comfortable on your Segway, explore Millennium Park, roll along the Lakefront, and more. As you go, learn little-known Chicago stories and tidbits, from mafia history to the innovations that changed the city.
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  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58

Chicago Walking Tour: Historic Skyscrapers

Chicago Walking Tour: Historic Skyscrapers

star-4.5
48
Explore the Loop's famous architecture during this 2-hour walking tour with an expert guide from the Chicago Architecture Foundation. Discover the beginnings of the Chicago School of Architecture through visits to some of the city's oldest skyscrapers, dating from the late 19th and early 20th centuries. This sophisticated, informative tour is a must-do for history and architecture buffs.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$30.00
From
$30.00

45-Minute Chicago Architecture Boat Tour from Chicago Riverwalk

45-Minute Chicago Architecture Boat Tour from Chicago Riverwalk

star-4
44
Enjoy unparalleled views of the Chicago skyline—and glimpse many of the city’s top landmarks—on this architectural boat tour. Pick from multiple convenient departure times, and hop aboard the open-air vessel right off the Chicago Riverwalk. As you trawl the Chicago River, spy skyscrapers and historical marvels from the Willis Tower to the Wrigley Building, and learn all about the Windy City’s world-famous architecture from your guide’s narration.
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  • 45 minutes
  • Free Cancellation
From
$25.00
From
$25.00

Chicago Walking Tour: A Walk Through Time

Chicago Walking Tour: A Walk Through Time

star-5
42
Travel through architectural history on this walking tour that covers Chicago's most famous buildings in chronological order. With a guide in the lead, there's no need to fuss over maps or worry about directions. Simply stroll along and listen to the in-depth guided commentary on Chicago's architectural history; you'll learn about each building and its importance in the architectural canon.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$30.00
From
$30.00

Ugly Buildings Tour

Ugly Buildings Tour

star-5
34
Chicago is the architectural capital of the country and has so many tours profiling these wonderful, beautiful buildings. Hiding around these architectural masterpieces, however, are UGLY BUILDINGS. This “educational roast” teases these buildings and creates a conversation on what makes a building pretty or ugly. These opinions are all subjective, and participants are encouraged to share their perspectives whether or not they agree. IMPORTANT NOTE: There are jokes about Trump Tower along with the person it is named after on this tour. There is also one swear word used, because it is an important part of a story. If you don’t think you would find these kinds of jokes funny, I recommend choosing any other architectural tour. There are so many stories and perspectives on Ugly Buildings I have not previously been able to share on any other tours. I am really excited to have you along for this experience that is unlike any other tour in Chicago!
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  • 2 hours
  • Free Cancellation
From
$30.00
From
$30.00

Chicago Walking Tour: Historic Treasures of Chicago

Chicago Walking Tour: Historic Treasures of Chicago

star-5
31
Get an insider's introduction to Chicago's most celebrated buildings during this architecture-focused walking tour of Michigan Avenue and State Street. Revisit the heyday of the skyscraper and visit stunning, Art Deco-era interiors, from the Palmer House Hotel to the Chicago Cultural Center. Admission to the Chicago Architecture Center is included, with an introduction by the docent.
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  • 2 hours
  • Free Cancellation
From
$30.00
From
$30.00

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