Chicago
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Viator
Small-Group Sightseeing Boat Tour in Chicago
The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights around the local waterways including the Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and many others. Come aboard our safe and seaworthy US NAVY built Rigid Inflatable Boat (RIB), and experience a unique & personal tour of the City!
5.0(95)
1h 30m
Chicago
- Free cancellation
- Likely to sell out
From
$89
No similar experiences found
Headout
Big Bus: Chicago Hop-on Hop-off Bus Tour
• Plan your Chicago itinerary without worrying about arranging travel with this 24/48/72-hour hop-on hop-off bus tour, hopping off unlimited times.
4.6(304)
1 Day
Chicago
- Free cancellation
- Instant confirmation
From
$40
No similar experiences found
Viator
Chicago Crime and Movies Tour
Mobsters and Movies takes you through the real haunts of Capone, Dillinger, and The Outfit—then shows you how the very same streets turned into movie magic. Walk the same corners seen in 'The Untouchables' and 'Public Enemies,' and hear how Chicago wrote the script for American gangster history. This isn’t just another sightseeing tour—it’s a front-row seat to crime, cinema, and the city that made them both. Your guides aren’t just storytellers—they’re trained true crime historians, film buffs, and Chicago insiders who bring every scene to life. Step inside exclusive interiors where real mobsters plotted and Hollywood crews once brought the Windy City to the Silver Screen. We take you deeper into the story than any other tour can. Expect vivid tales, insider trivia, and behind-the-scenes stories that make Chicago’s gangster past feel as real as the movies it inspired.
5.0(58)
1h 30m
Chicago
- Free cancellation
From
$35
No similar experiences found
Viator
Chicago Walking Tour: Connecting Past and Present
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. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.
5.0(42)
1h 45m
Chicago
- Free cancellation
From
$35
No similar experiences found
Viator
Chicago Shoreline Adventure Boat Tour
This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Williard Marine, which provides a unique and interesting touch to the normal tour experience. Being both sturdy in the water, and fast! Reaching up to speeds of 35 Knots! We work hard to provide historical context for our great city, as well as provide an exhilarating experience through the use of high speed runs and spins!
5.0(38)
1h 30m
Chicago
- Free cancellation
- Likely to sell out
From
$90
No similar experiences found
Viator
Chicago Haunts and Hooligans Tour
Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a recent transplant to Chicago or have lived among the Windy City’s ‘others’ for years, you’re about to get a haunted history that may leave you with more memories than you dare to retain. Tours begin at the haunted Harry Caray’s Italian Steakhouse in downtown Chicago. A costumed guide will lead tour goers on a walking journey exploring the creepy past of one of Chicago’s most famous bootleggers, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home.
5.0(37)
1h 30m
Chicago
- Free cancellation
- Likely to sell out
From
$35
No similar experiences found
Viator
Chicago Photo Walk to Bean and Landmarks
We’ll begin our photo walk in Millennium Park with portraits at Cloud Gate (The Bean), one of Chicago’s most iconic landmarks. During our time together, we’ll visit a rooftop spot for skyline views, cross the scenic DuSable Bridge, and stop by the elegant Wrigley Building - all perfect for beautiful photos. Along the way, I’ll guide you with natural poses and creative ideas, helping you feel relaxed and confident. By the end of this walk, you’ll not only have a beautiful photo gallery - you’ll have also visited many of the MUST-SEE places in downtown Chicago.
5.0(31)
1 Hour
Chicago
- Free cancellation
From
$169
No similar experiences found
Viator
Chicago Scenic Driving Tour
Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic Driving Tour will start by meeting our knowledgeable Guide/Driver who will pick you up at your hotel or other location provided and then proceed with the exploration of the beautiful windy city.
5.0(21)
2 Hours
Chicago
- Free cancellation
From
$315
No similar experiences found
Viator
History and Architecture of Chicago Loop Walking Tour
Discover the rich history and architecture of downtown Chicago with local expert Dave Lineal. Walking underneath the soaring buildings, we will learn how Chicago grew to become a global force in culture, commerce, and architecture. How did this roaring city come to be? We will hear the tales of Chicago history immersed in the places where it happened -- exploring historic building interiors like the world's oldest skyscrapers, City Hall, and the old library. This deep dive in city history and architecture aims to deepen our appreciation of what Chicago is today.
5.0(20)
2 Hours
Chicago
- Free cancellation
- New
From
$30
No similar experiences found
Viator
Private Chicago History Museum Tour
Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life through captivating stories, insider insights, and exclusive information tailored to your interests.
5.0(18)
2 Hours
Chicago
- Free cancellation
- Private tour
- Likely to sell out
From
$163
No similar experiences found
Viator
Prairie Avenue Haunted History Tour and Ghost Hunt
Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this amazing area, the most desirable address in the city before the fire. Many of the incredible homes are still standing and the spirits linger, waiting to divulge their secrets in a haunted history tour and ghost investigation in one of Chicago's most prestigious places.
5.0(12)
2h 20m
Chicago
From
$40
No similar experiences found
Viator
Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline
Discover the architectural soul of Chicago on a thoughtfully curated half-day city tour. Travel through the city’s most influential districts, from historic riverfront landmarks to groundbreaking modern skyscrapers. Explore the Loop’s civic, financial, and architectural core, admire world-renowned towers, and experience Chicago’s most celebrated public spaces. This small-group tour offers a comprehensive introduction to Chicago’s skyline, history, and urban design, concluding with a panoramic skyline view before returning guests to the original pickup point. Ideal for first-time visitors and architecture enthusiasts alike. Explore Chicago’s iconic riverfront skyscrapers and historic bridges See legendary architecture including Willis Tower and Marina City Discover the heart of Chicago’s financial, civic, and architectural power Pass by Millennium Park and spend time at Cloud Gate (The Bean) Enjoy a panoramic Chicago skyline view, included for all guests
5.0(11)
3 Hours
Chicago
- Free cancellation
- Special offer
- New
From
$41
No similar experiences found
Viator
Lincoln Park Zoo & Nature Museum Private Walking Tour
Discover the wild heart of Chicago on our guided walking tour through Lincoln Park, where nature and history meet in one unforgettable experience. What sets our tour apart is the seamless blend of three iconic destinations—the Peggy Notebaert Nature Museum, the lush Lincoln Park Conservatory, and the vibrant Lincoln Park Zoo—curated into one dynamic, story-filled journey led by a knowledgeable local guide. You'll marvel at the butterflies in flight, wander through exotic gardens under glass, and encounter wildlife from around the world—all while uncovering the hidden history and surprising beauty of this beloved urban oasis. Whether you're a first-time visitor or a lifelong Chicagoan, this tour offers fresh insights, natural wonders, and photo-worthy moments at every turn. Book now and see why Lincoln Park is one of Chicago’s most treasured gems!
5.0(10)
2 Hours
Chicago
- Free cancellation
- Private tour
From
$275
No similar experiences found
Viator
Chicago Movie Locations Tour
Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigley Field exterior (Ferris Bueller's Day Off), the Chicago Board of Trade exterior (The Dark Knight), Union Station's staircase (The Untouchables), and Millennium Park's Cloud Gate (Source Code). Enjoy a seamless and comfortable experience exploring these famous sites.
5.0(10)
3 Hours
Chicago
- Free cancellation
From
$315
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Viator
Intro to Chicago Architecture
Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from early, classically inspired European styles to bold American Art Deco and Modernist innovations to today’s Contemporary designs that continue to set the pace for world-leading architecture. As you journey through Chicago’s spectacular skyscraper canyons and stunning interiors, you’ll see how economics, technology, creativity, and gritty determination shaped Chicago’s ever-evolving skyline. Whether you’re a visitor or you’re a Chicagoan who has never explored the architectural masterpieces you see every day, join us today on this enlightening adventure.
5.0(9)
1h 45m
Chicago
- Free cancellation
- New
From
$35
No similar experiences found
Viator
Candle Making Experience Near Museums & Millennium Park
Step into our vibrant candle-making studio and unleash your creativity! Craft candles with friends and family, blending custom scents in a welcoming space. Take home your masterpiece the same day, making memories and experiencing Chicago in a unique, unforgettable way. Join us for a non-traditional workshop designed for instant gratification and lasting inspiration!
5.0(8)
2 Hours
Chicago
- Free cancellation
From
$75
No similar experiences found
Viator
Chicago West Loop Pizza Crawl
Taste four different styles of pizza in about three hours. Learn about Chicago's 10 pizza styles, and discover why there's more to The Windy City than just deep-dish. Go back in some of the kitchens to see how pizzas are made, and taste the differences. Expert doughcents will share the history of Chicago pizza as well other interesting tidbits about the neighborhood you're exploring. We need to know if there are any vegetarians in your group the day before please.
5.0(7)
3 Hours
Chicago
From
$79
No similar experiences found
Viator
Private Chicago Foodie Tour
Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza, Garrett’s Popcorn, and Do-Rite Donuts while exploring top city landmarks such as the Tribune Tower, Wrigley Building, and Buckingham Fountain. Led by a friendly local guide, this experience blends Chicago’s most famous eats, rich culture, and great photo ops — the perfect way to enjoy the best of the Windy City in one delicious day. Tour Ticket Includes: • 1 Portillo’s hot dog • 1 small Garrett’s Popcorn • 6" Al’s Italian Beef Sandwich • 1 slice of authentic Chicago deep dish pizza
5.0(6)
4 Hours
Chicago
- Free cancellation
- Private tour
- Likely to sell out
From
$288
No similar experiences found
Viator
Chicago Walking Tour of Highlights with Free Bike or Kayak Rental
This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking Tour. During this 2-hour Walking Tour of Chicago, stroll through downtown’s beautiful streets as expert local guides share rich history, colorful characters, and insider tips to enhance your list of Things to do in Chicago. Your experience includes a FREE 2-hour bike or kayak rental—bike the Lakefront Trail or kayak on Lake Michigan for unforgettable skyline views. Bobby’s Bike Hike tours are nationally recognized by National Geographic, USA Today, and Condé Nast Traveler for excellence in storytelling and urban exploration. You’ll see the landmarks that define Chicago: Millennium Park, the Chicago Riverwalk, the Wrigley Building, the Chicago Theatre, and the famed Magnificent Mile. Covering 1.5 miles (2.25 km) of easy, flat terrain, this tour offers a complete and memorable introduction to the city.
5.0(6)
2 Hours
Chicago
- Free cancellation
From
$45
No similar experiences found
Viator
Chicago Guided Tour in Spanish
Because we don't just show you the city... we tell you, and we make you live it! At ChicaGo Turismo you will discover the true essence of Chicago: its vibrant history, imposing architecture and hidden corners that few know. Our guides are passionate and certified experts, with charisma, solid knowledge and an authentic connection to the city. We offer 100% Spanish tours, designed especially for Spanish speakers who want to know Chicago thoroughly, with cultural context, fascinating stories and a touch of humor and excitement. We walk, explore, observe and feel each space with curiosity and respect, so that you live an unforgettable, close and authentic experience.
5.0(6)
2h 45m
Chicago
- Free cancellation
From
$45
No similar experiences found
Viator
Chicago Seasonal Stroll Walking Tour of Holiday Attractions
There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through the Chicago Loop, Millennium Park, & the Magnificent Mile with an internationally recognized tour company proudly headquartered right here in Chicago. Our entertaining guides will spark your holiday spirit with fun facts, cultural insights, & the very best seasonal décor—like the surprising fact that Rudolph the Red-Nosed Reindeer was created in Chicago! Along the way, you’ll marvel at the iconic Christmas window displays of the original Marshall Field’s store, admire Chicago’s official Christmas tree, Mag Mile lights, and take in the festive Millennium Park ice skating rink. You’ll even enjoy VIP access—no waiting in line—to the legendary Christkindlmarket, the city’s beloved German holiday market. If you’re searching for Things to do in Chicago during the holidays, this experience is a perfect fit. Note: This is a walking tour only.
5.0(5)
2 Hours
Chicago
- Free cancellation
From
$45
No similar experiences found
Viator
Chicago BYOT Screen Printing Workshop: Make Your Own Art Tee
Remade in Chicago is the upcycling studio where surplus textiles are transformed into one-of-a-kind wearable art, braided rugs, and hand-stitched quilts. We host public and private workshops, and we love to partner with DIY-enthusiasts on custom projects. Our aim is to inspire folks to creatively modify their wardrobes, extend the life of cherished items, and be savvy textile consumers.
5.0(5)
1h 30m
Chicago
- Free cancellation
From
$60
No similar experiences found
Viator
Private Chicago Guided Tour with Hotel Pickup
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. During this tour, you will explore great locations in Chicago like the Richard J. Daley Center. There will also be a photo stop at the Lakefront Trail and South Michigan Avenue. Don't miss the Grant Park, Cloud Gate and of course the Downtown / The Loop. This private tour will finish off at your hotel in Chicago.
5.0(5)
4 Hours
Chicago
- Free cancellation
- Private tour
- Special offer
From
$794
No similar experiences found
Viator
Self-Guided Chicago Loop Tour Explore the City at Your Own Pace
Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skyscrapers and hidden architectural gems, allowing you to explore at your own pace. Uncover the rich history from the Great Fire of 1871 to the architectural masterpieces that define the skyline. Stroll past renowned theaters, museums, and captivating public art pieces that contribute to the city’s creative spirit. The Loop offers a unique perspective on Chicago's past and present, whether it's your first visit or a familiar stroll. — Self-guided exploration of Chicago’s historic Loop area — Learn about the city’s architectural innovations and history — Visit iconic landmarks like the Art Institute and Millennium Park — Perfect for first-time visitors or seasoned Chicagoans alike
5.0(4)
2 Hours - 2h 30m
Chicago
- Free cancellation
- Private tour
From
$10
No similar experiences found
