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30 results | All Chicago Tours

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Chicago Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architecture River Cruise

star-5
6875
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
$44.69
From
$44.69
Taking safety measures

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1107
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
  • Taking safety measures
From
$46.00
From
$46.00
Taking safety measures

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
2111
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
  • Taking safety measures
From
$27.00
From
$27.00
Taking safety measures

Chicago Architectural River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architectural River Cruise

star-4.5
711
See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$49.05
From
$49.05
Taking safety measures

Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

star-4.5
557
Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
Taking safety measures

Chicago in a Day: Food, History and Architecture Combo Tour
Likely to Sell OutLikely to Sell Out

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

star-5
153
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
  • Taking safety measures
From
$104.00
From
$104.00
Taking safety measures

Chicago Night Crimes Bus Tour

Chicago Night Crimes Bus Tour

star-4.5
113
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
  • Taking safety measures
From
$51.00
From
$51.00
Taking safety measures

Chicago City Minibus Tour with Optional Architecture River Cruise

Chicago City Minibus Tour with Optional Architecture River Cruise

star-5
445
Explore Chicago's iconic landmarks on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore downtown and Northside neighborhoods. You have a chance to get out and visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.
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  • 2 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
$39.95
From
$39.95
Taking safety measures

Chicago Walking Tour: Art Deco Skyscrapers
Likely to Sell OutLikely to Sell Out

Chicago Walking Tour: Art Deco Skyscrapers

star-4.5
79
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
  • Taking safety measures
From
$30.00
From
$30.00
Taking safety measures

Field Museum of Natural History Admission Tickets

Field Museum of Natural History Admission Tickets

star-4.5
149
Delve deep into the world of natural history with this Field Museum admission ticket in Chicago. Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the free daily tours, led by Field Museum docents.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$26.00
From
$26.00
Taking safety measures

Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

star-5
539
Enjoy a quintessential Chicago experience when you go on an architecture-themed river tour. Pick from multiple convenient start times, and board your vessel—the Lady Liberty—directly from the Chicago Riverwalk. Your trained docent guides will give you a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and you can spy landmarks like the Marina City towers and Navy Pier from the water’s edge.
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  • 1 hour 30 minutes
  • Taking safety measures
From
$56.00
From
$56.00
Taking safety measures

90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
1303
Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
Taking safety measures

Chicago Private Tours

Chicago Private Tours

star-5
144
Have only a short stay planned in Chicago? Make the most of your time in the Windy City, and see more of the city in less time, when you book a private driving tour of Chicago. Pick between several convenient tour times, and meet your guide and driver directly at your hotel. Over the course of your excursion, you’ll make stops at highlight attractions like the Lincoln Park Conservatory, Millennium Park, and Museum Campus. You’ll also learn about Chicago’s history and can spy other remarkable sights as you go.
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  • 3 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
$425.34
per group
From
$425.34
per group
Taking safety measures

Chicago Walking Tour: Historic Treasures of Chicago

Chicago Walking Tour: Historic Treasures of Chicago

star-5
24
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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  • 1 hour 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$30.00
From
$30.00
Taking safety measures

Train & Walking Tour: Chicago's Prairie District - Street of the Elite

Train & Walking Tour: Chicago's Prairie District - Street of the Elite

star-5
9
Step off the typical tourist trail, and discover one of Chicago’s oldest and most scenic neighborhoods, on this walking tour of the Prairie District. Meet your guide in the morning at the Chicago Athletic Association, and set off with just a small group for company. The Prairie District is just a short L ride away; you can look forward to seeing the Second Presbyterian Church, Glessner House, Motor Row, and otherwise discovering how Chicagoans lived at the turn of the 20th century.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$90.00
From
$90.00
Taking safety measures

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.
More
  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58

Art Institute of Chicago Skip-the-Line Small-Group Guided Tour

Art Institute of Chicago Skip-the-Line Small-Group Guided Tour

star-5
24
Explore one of the country’s great art museums—and discover many of its collection highlights—on this small-group Art Institute of Chicago tour. Meet your guide right out front, and see works from artists the likes of Picasso, Chagall, Seurat, O’Keeffe, and many more. As you go, your guide will share the stories behind the masterpieces, and will help bring the history of the museum and its collection to life.
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  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
From
$100.70
Price varies by group size
From
$100.70
Price varies by group size

Ugly Buildings Tour

Ugly Buildings Tour

star-5
23
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!
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$30.00
From
$30.00
Taking safety measures

Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket

Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket

star-5
21
The Art Institute of Chicago houses one of the finest American and Impressionist painting collections in the world, but it can be overwhelming to explore on your own. Remove the guesswork and maximize your time inside the museum on a private tour that covers major highlights by Picasso, Chagall, Warhol, Hopper, and others. Plus, there's no waiting to get inside, as the tour includes a skip-the-line ticket.
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  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
From
$153.70
Price varies by group size
From
$153.70
Price varies by group size

Workers Cottages of Oldtown Triangle Walking Tour

Workers Cottages of Oldtown Triangle Walking Tour

star-5
14
This tour will show you many of these delightful cottages and the different styles they were designed and constructed in. You will also learn about their history and unique part of the growth of the city of Chicago. Plus you will hear about other fascinating Chicago history that dates back 150 years and beyond! The Oldtown Triangle is one of the oldest and most quaint areas of the city - an area that many Chicagoans love and cherish. You will feel like you have left the hustle and bustle of the city and will instantly be transported to another place, another time, specifically the late 1800's!
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  • 1 hour 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$35.00
From
$35.00
Taking safety measures

Underground Donut Tour - West Loop & Restaurant Row

Underground Donut Tour - West Loop & Restaurant Row

star-5
13
Head to one of Chicago’s top neighborhoods for food lovers—and try donuts from four of the Windy City’s top specialty bakeries—on this indulgent walking tour. Meet your guide at the Chicago French Market in the morning, and come hungry: you’ll enjoy four different donuts, each representing different culinary styles and traditions. As you go, wander the West Loop and Restaurant Row, and learn more about Chicago’s dining scene.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$30.00
From
$30.00
Taking safety measures

Saturday Chicago Pizza History and Tastings Bus Tour

Saturday Chicago Pizza History and Tastings Bus Tour

star-5
6
Foodies will enjoy this tour of Chicago that focuses on one of the city’s most popular dishes: pizza. Although your guide can’t tell you once and for all whether Chicago or New York has the best pizza in the USA, they will teach you about Chicago’s ten different types of pizza, let you sample four, and give you exclusive access to pizza kitchens. A fun tour for all pizza lovers.
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  • 3 hours 30 minutes
  • Taking safety measures
From
$90.00
From
$90.00
Taking safety measures

Full-Day Small-Group Tour of Chicago Neighborhoods with Lunch and Dinner

Full-Day Small-Group Tour of Chicago Neighborhoods with Lunch and Dinner

star-5
6
Explore Chicago like a local—and visit the city’s distinctive, characterful neighborhoods, in addition to its major landmarks—on this full-day tour. Set off from downtown with just a small group for company, and leave the driving to your guide—you’ll explore dozens of Windy City neighborhoods, from Hyde Park and Bronzeville to Lincoln Park and the Gold Coast. Learn all about Chicago culture and history as you go.
More
  • 8 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$175.00
From
$175.00
Taking safety measures

Chicago Walking Tour: Connecting Past and Present

Chicago Walking Tour: Connecting Past and Present

star-5
2
This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying architectural styles and see how older structures connect to new skyline additions. On this tour, we'll make seven stops in downtown Chicago where we can compare the histories and styles of buildings located within sight of each other. The tour features 19th-Century Commercial, Beaux-Arts, Mid-Century Modern and Postmodern buildings, as well as the latest in architecture from Frank Gehry, Renzo Piano and Adrian Smith. At each stop, we’ll look at the connections between the past and present and discover what inspires design today. The tour culminates with a visit to Millennium Park, where world-class art and architecture combine, creating a unique urban fabric.
More
  • 1 hour 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$30.00
From
$30.00
Taking safety measures

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