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25 results | All Chicago Tours

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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

Chicago Private Tours

Chicago Private Tours

star-5
145
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
From
$425.34
per group
From
$425.34
per group

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

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

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

90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
1363
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
From
$40.00
From
$40.00

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1145
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 Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architecture River Cruise

star-5
7004
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
  • Free Cancellation
From
$40.33
From
$40.33

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
919
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 audio commentary onboard gives you insight into the city's colorful history.
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  • 2 hours
  • Free Cancellation
From
$26.10
From
$26.10

30 Minute Lake Michigan Speedboat Ride

30 Minute Lake Michigan Speedboat Ride

star-4.5
123
Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.
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  • 30 minutes
From
$34.75
From
$34.75

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

star-5
297
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. Upgrade your tour to include three pours of local craft beer.
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  • 3 hours
  • Free Cancellation
From
$69.99
From
$69.99

Chicago CityPASS

Chicago CityPASS

star-4.5
335
Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Shedd Aquarium, Skydeck Chicago (Opening with reimagined experience in Spring 2021), and the Field Museum plus your choice of admission to 3 of the following attractions: Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Chicago, and the 360 CHICAGO Observation Deck. Also enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers.
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  • 9 days
  • Free Cancellation
From
$109.00
From
$109.00

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

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

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

star-5
27
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

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
23
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
From
$35.00
From
$35.00

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
9
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.
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  • 8 hours 30 minutes
  • Free Cancellation
From
$175.00
From
$175.00

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
From
$90.00
From
$90.00

Chicago Walking Tour: The Magnificent Mile

Chicago Walking Tour: The Magnificent Mile

star-5
5
Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier shopping district. Hear the secrets and stories behind the striking buildings on North Michigan Avenue that have become architectural icons. Developed over the past 100 years, the street includes historically-inspired architecture in Parisian, Gothic, neoclassical and Art Deco styles sprinkled among Modern and 21st Century buildings. You’ll see skyscrapers, vertical malls, hotels, residential towers and some buildings that were designed to embody the brands sold inside.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$30.00
From
$30.00

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.
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  • 1 hour 45 minutes
  • Free Cancellation
From
$30.00
From
$30.00

Family walking tour in Chicago

Family walking tour in Chicago

Where does the Name Chicago come from? Experience the most rewarding adventure with your family on our exclusive family walking tour. Our family-friendly local professional guide will make sure the kids have as much fun sightseeing as adults. The well-informed guide will take you on a 2-hour long walking tour. The tour has an easy pace and includes a stroll around the city center, highlighting the famous cultural and architectural sites. The whole family will have fun learning about Chicago’s fascinating and interesting sites. The stories shared by the guide are guaranteed to provide a few giggles as you wind down the off beaten paths of the city. Why is Chicago city known as the “Home of the Skyscraper”? Are you ready to find out and see?
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  • 2 hours
From
$229.45
Price varies by group size
From
$229.45
Price varies by group size

Private Chicago Tour with Driver and tour Guide. Hotel pick up included

Private Chicago Tour with Driver and tour Guide. Hotel pick up included

One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour guide take you around the most important sites and locations of Chicago. Being a private tour, stop whenver you want to take pictures and also explore by foot specific locations. Pick up is included from your hotel or place of choice inside the city and downtown Chicago. Please include this information as well as a contact number when booking. This private tour will give you a great experience to get to know Chicago. This is a 4 hour private tour with driver and separate tour guide. Here are some examples of what you will see: - Richard J. Daley Center - Lakefront Trail - South Michigan Avenue - Grant Park - Cloud Gate - Downtown / The Loop - South Riverside Plaza - The Art Institute of Chicago - Navy Pier - Buckingham Fountain This private tour will finish off at your hotel in Chicago.
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  • 4 hours
  • Free Cancellation
From
$403.55
Price varies by group size
From
$403.55
Price varies by group size

Walking Tour of Chicago Riverwalk

Walking Tour of Chicago Riverwalk

Chicago's Riverwalk is a bevy of impressive buildings, gardens, eateries, and beyond. Spend two hours wandering with an expert local at your side. Explore the art, architecture, and all the little hidden spaces with the absolute best experience in one of the most essential areas of Chicago. Make your way from the Magnificant Mile to the four distinct districts of the Riverwalk while tales of Chicago delight your ears and sights tickle your eyes.
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  • 2 hours
  • Free Cancellation
From
$32.00
From
$32.00

Chicago Architecture Walking Tour: Debunking Architecture Myths & Urban Legends

Special Offer

Chicago Architecture Walking Tour: Debunking Architecture Myths & Urban Legends

If you’ve taken any tour in Chicago, you’ve likely heard some common urban myths masked in “truth” because the tour guide supposedly knows best. But most tours are basically regurgitated scripts that perpetuate these myths -- and then the guests who take those tours spread those myths to their local friends, and the myths become “truth”…but they’re not true. On this all-outdoors tour, we tell some of the most commonly told urban myths in a fun “Two Truths & a Lie” format, where you’ll be given the TRUTH behind each myth told on so many tours, and we’ll add a few more truths to that. Did Al Capone really operate a speakeasy in the Jewelers’ Building? Was the Carbide & Carbon Building modeled after a champagne bottle in order for the architects to thumb their noses at Prohibition? Is the Civic Opera Building meant to represent a “throne” facing away from New York? Come join us on a debunking mission through downtown Chicago and its riverfront, with gorgeous views along the way!
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  • 2 hours
  • Free Cancellation
From
$26.40
$33.00
$6.60 savings
From
$26.40
$33.00
$6.60 savings

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The answers provided below are based on answers previously given by the tour provider to customers’ questions.
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