Top Chicago Sightseeing Tours - page 7

200+ results

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Chicago is renowned for its architecture—and this immersive walking tour offers the perfect way to discover its highlights. Pick from a wide range of start times, meet your private guide right in the Loop, and set off on foot. In between seeing renowned landmarks like the Chicago Cultural Center, public art by Picasso, and other heritage buildings, you’ll learn all about the city’s history.

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Private 2-Hour Walking Tour: Chicago Loop Interior Architecture

2 hours

from $325

Price varies by group size

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Chicago All Day Water Taxi

20 minutesFree Cancellation

from $36

Embark on an exclusive journey through Chicago's storied past with a private tour unveiling the city's 1920s Art Deco and Art Moderne architectural wonders. Led by a knowledgeable local guide, delve into Chicago's pivotal role in shaping the global Art Deco movement, an era synonymous with innovation and elegance. Marvel at the intricate facades and lavish designs adorning the city's iconic buildings, each a testament to the opulence and creativity of the Jazz Age. Gain profound insights into the architectural evolution that defined Chicago's skyline, from the roaring twenties to the present day. This immersive experience promises a deep dive into the vibrant history and enduring legacy of Chicago's architectural heritage, offering a unique perspective on the city's rich cultural tapestry.

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Chicago Loop Private Walking Tour with a Guide

2 hoursFree Cancellation

from $131

Price varies by group size

Live the mythical Route 66 as it should be: at your own pace, with freedom and with the feeling of being walking a living history. This audio guide accompanies you from Chicago to Los Angeles, transforming each stretch of road into an experience full of context, curiosities and stories that give meaning to the journey. You don’t just drive – you understand the landscapes, cities and small towns that marked the American dream. No schedules, no groups and no rush, just you, the road and a voice that guides you at the right time. If you’ve always dreamed of doing Route 66 for real, this audio guide is the most authentic and simple way to live it.

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Guided Audio Road Trip Route 66

6 daysFree Cancellation

from $30

Per group

Entry ticket and self-guided audio tour of Skydeck and the city of Chicago are available in a separate app — the WeGoTrip app. You will receive an email from WeGoTrip with the link to download the app with the ticket and the digital guide. The digital guide includes maps, photos, scripts, and audio commentary. You will see Chicago from above and on foot with a Skydeck ticket and self-guided audio touring-app audio tour. Soak up history and panoramas of the place that Frank Sinatra called "My kind of town" and after your visit to the Skydeck, continue your journey on foot, uncovering the stories behind what you saw. Visit Millennium Park, cross the Chicago River and stroll along the Magnificent Mile

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Chicago Willis Tower Skydeck Ticket and Audio Tour with City Walk

2 hours

from $79

Our tour will take you through Millennium Park, starting at the Millennium Park Welcome Center. We’ll wander past shining sculptures, playful fountains, and peaceful gardens, all while soaking in the city’s energy, ending at Queen’s Landing, where the city meets the lake, and the skyline stretches as far as you can see. You'll learn the history of the city, see the sites, learn about what you are seeing and be guided step by step by our walking tour app.

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Chicago’s Millennium Park Self Guided Audio GPS Walking Tour

1 hour to 1 hour 30 minutesFree Cancellation

from $10

Chicago is inseparable from its Black history, where local pioneers helped shape the city’s story. On this self-guided audio tour through downtown Chicago, you’ll hear untold stories of Black excellence, resilience, and activism that transformed both the city and the nation. From Underground Railroad stations to civil rights battlegrounds, you’ll discover how Chicago became a beacon for those seeking freedom and opportunity. Starting at the site of Jean Baptiste Point DuSable’s mansion near the Chicago River, you’ll follow the footsteps of the city’s founder: a Black man who established Chicago’s first trading post in the 1770s. You’ll walk through the heart of the Loop, exploring sites where pioneering entrepreneurs like John Jones built businesses that became platforms for activism. The tour ends at Grant Park, where Barack Obama delivered his historic presidential acceptance speech in 2008 – a moment that represented the culmination of generations of struggle.

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Resilience and Revolution: Audio Tour of Chicago’s Black History

2 hours to 2 hours 30 minutesFree Cancellation

from $15

Chicago Self-Guided Walking Audio Tour

1 to 2 hours

from $5

Per group

GPS Audioguide app: From Loop to Millennium Park (Offline).

Chicago, a city with undeniable charm, awaits you for a walking exploration of its 25 must-see attractions. From the Riverwalk to Marina City to the famous Cloud Gate, this tour takes you through the history and architecture of Windy City. See iconic venues like the Chicago Theatre and Willis Tower, while learning fascinating stories about Al Capone and Prohibition. An enriching experience for architecture, history and gastronomy lovers, all in one day. - 7.2 km tour through points of interest in Chicago - Discover the historical and modern heritage of the city - Explore at your own pace with captivating audio stories - Ideal for travelers in a hurry or those on a quick visit to Chicago

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Chicago Audio Guided Walking Tour 3h and 25 Audio Commentaries

3 hoursFree Cancellation

from $7

Per group

Uncover the essence of Chicago's sports culture on this guided tour through the downtown area. Learn about the city’s iconic sports figures, explore fascinating stories, and discover the hidden sports landmarks that define the lives of Chicago fans. This tour offers a unique perspective on how sports are woven into the fabric of the city, providing insights that only a local guide can share. Whether you're a die-hard sports fan or just curious about the city's history, this tour is perfect for anyone looking to delve deeper into Chicago's athletic legacy. - App-Guided tour focusing on Chicago's rich sports history - Explore the downtown area and discover hidden sports icons - Learn about legendary figures and their impact on the city - Ideal for sports enthusiasts and those interested in local culture - Opportunities to purchase Chicago sports-related souvenirs

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Chicago Sports Legends Guided Tour

2 hoursFree Cancellation

from $5

Likely to Sell Out

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. Tour Chicago in a small group perfect for busy sidewalks and get up close to monumental art! Join one of our expert guides on this unique and exclusive 2.5 hour guided walking tour of Downtown Chicago. Highlights Include: Edward Kemeys’s “Lions” Juame Plensa’s “Crown Fountain” Anish Kapoor’s “Cloud Gate” (The Bean) Eduardo Kobra’s “Muddy Waters” Pablo Picasso’s “Untitled” Joan Miro’s “Chicago” Alexander Calder’s “Flamingo” Marc Chagall’s “Four Seasons” Louis Comfort Tiffany Art Glass Creation Augustus St. Gaudens “Abraham Lincoln” Marcel Francois Loyau “Clarence Buckingham Fountain”

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Exclusive Downtown Chicago Guided Walking Tour 12ppl Max

2 hours 30 minutesFree Cancellation

from $52

Price varies by group size

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise. Witness the stunning skyline as you glide across the water, leading up to the spectacular fireworks display at Navy Pier. This 1.5-hour cruise offers a unique perspective of the city while providing a relaxed atmosphere for friends and family to gather and enjoy the show. Boarding begins 15 minutes prior to departure, so arrive early to secure your spot and make the most of this dazzling experience. - 1.5-hour cruise featuring panoramic views of Chicago's skyline - Marvel at the iconic fireworks show off Navy Pier - Departing and returning to 111 N Lake Shore Drive

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Chicago Fireboat Fireworks Cruise

1 hour 30 minutesFree Cancellation

from $57

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Original Chicago Prohibition Bus Tour

4 hoursFree Cancellation

from $55

Venture along Michigan Avenue on an interactive tour to uncover Chicago's hidden gems and iconic landmarks. Dive into the city's rich history, answer trivia, and complete challenges for a unique experience blending sightseeing with gaming. Explore the Magnificent Mile and Cultural Mile with this unique adventure: Solve puzzles, explore the city, and find hidden gems at your own pace. Try a new type of experience with your smartphone, the perfect mix between a walking tour, sightseeing, and a scavenger hunt.

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Michigan Avenue Rendezvous GPS App Walking Tour Mobile Game

1 to 2 hoursFree Cancellation

from $17

Price varies by group size

Logan Square Walking Tour Experience

1 hour 20 minutesFree Cancellation

from $35

Discover Chicago's soaring ambition and neighborhood soul with your self-guided audio tour, allowing you to explore America's most architecturally significant city at your own pace. Begin at Millennium Park where Anish Kapoor's Cloud Gate reflects the skyline that pioneered skyscraper design and continues to push architectural boundaries today. Wander along the Chicago Riverwalk where boat tours explain how the city reversed the river's flow and rebuilt in steel and stone after the Great Fire of 1871. Marvel at the ICAs world-class collection. Explore the Magnificent Mile's shopping and historic Water Tower, then discover the vibrant neighborhoods where Polish, Mexican, and African American communities have shaped Chicago's culture. Experience the blues at clubs where Muddy Waters and Buddy Guy defined a genre, then savor deep-dish pizza in the taverns that perfected this Chicago original.

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Discover Chicago: A Self-Guided Walking Tour

8 hours 30 minutesFree Cancellation

from $10

Explore the underground drinking culture of Chicago during the Prohibition era on this captivating app-guided walking tour. Uncover the secrets of hidden bars and speakeasies while learning about the city's notorious figures like Al Capone. This evening tour blends fascinating stories of gangsters and bootleggers with Chicago's vibrant cocktail and beer scene, making it an ideal experience for history lovers and cocktail enthusiasts alike. - Visit intriguing speakeasy-style venues and secret bars in Chicago's Loop - Discover the rich history of Prohibition and its impact on the city - Optional purchase of drinks and food at most stops, with recommendations provided - Perfect for history buffs and those seeking a unique night out in Chicago

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Sip Happens: Chicago Loop Prohibition Tour

1 hour 30 minutes to 2 hoursFree Cancellation

from $5

This 45-minute self-guided walking tour explores the bizarre history beneath Wicker Park’s elegant surface. Led by a longtime resident, you will discover the neighborhood’s transition from a wealthy enclave to a gritty artist hub and its modern gentrification. Key Highlights: * Radical History: Learn about labor leader Lucy Parsons and the search for hidden bombs in the park. * Beer Baron Row: Hear tragic tales of murder and madness tied to grand Victorian mansions. * Quack Medicine: Discover how Theophilus Noel’s "Vita-Ore" empire funded iconic local architecture. * Mob Intrigue: Visit the former Russian Baths where mobsters met in steam rooms to avoid FBI wires. * Massacre Connections: See where the St. Valentine’s Day Massacre was planned and its getaway car destroyed.

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Bizarre Wicker Park: Medicine and Mobsters Self-Guided Audio Tour

45 minutes to 1 hour 15 minutesFree Cancellation

from $10

Likely to Sell Out

Chase away your Monday blues with Chicago’s coolest concert at sea! Hop aboard the historic Tall Ship Windy for a 2-hour live blues music cruise on Lake Michigan, featuring city skyline views and a rotating roster of top local and international artists. With a full-service bar and plenty of space to move, relax, and dance, this floating music event blends unbeatable atmosphere with legendary sounds—perfect for date nights, group outings, or music lovers looking for a summer highlight. VIP boarding upgrades and kid discounts available. Book early; these shows sell out fast!

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Monday Night Concert Series: Blues and Views Aboard Tall Ship

2 hours

from $81

Discover the rich history and dynamic transformation of Hyde Park on this engaging walking tour. Delve into the neighborhood's evolution from a lakeside retreat for the elite to a vibrant, diverse community shaped by migration, policy, and social change. Explore iconic landmarks like the Museum of Science and Industry while gaining insight into the impacts of racial segregation and urban renewal. This tour is designed for history buffs and urban studies enthusiasts, offering a nuanced perspective on the intersection of race and community development. - Walk through Hyde Park and learn about its historical significance - Visit key sites related to civil rights and urban policy - Understand the neighborhood's transformation and ongoing challenges - Perfect for history lovers and those curious about social dynamics

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Hyde Park Walking Tour History Race and Urban Change

3 hoursFree Cancellation

from $5

Discover the stories, styles, and spirit that built Chicago into the architectural capital of the world. On this walking tour through the Loop, you’ll explore the birthplace of the skyscraper, visit landmarks like the Chicago Theatre, the Pablo Picasso at the Daley Plaza, and Millennium Park, and see how the city rose from the Great Fire to define modern design. Led by a friendly local guide who’s passionate about Chicago’s history and architecture, this tour brings the skyline to life one building, story, and photo stop at a time. Whether you’re an architecture enthusiast, a first-time visitor, or a curious local, you’ll walk away seeing Chicago in a whole new way.

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Downtown Chicago Loop Walking Tour (Private)

2 hoursFree Cancellation

from $27

643

Chicago Gangster History Walking Tour of River North

2 hoursFree Cancellation

from $40

Price varies by group size

Route 66, known as "The Main Street of America", runs through eight states from Chicago to Santa Monica. EN route to Illinois, POR Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California. Along DE way, it connects iconic cities such as St. Louis, Tulsa, Amarillo, Albuquerque, Flagstaff and Los Angeles, offering a unique experience through varied landscapes, from the Midwest Plains to the Southwest Deserts, each with its own history and culture. Route Chicago : 50 points Route DE Chicago to St. Louis : 56 points Route San Luis : 13 points Route DE San Luis to Joplin : 56 points Route Joplin to Oklahoma city : 29 points Route DE Oklahoma City to Amarillo : 27 points Yellow Route to Santa Fe : 39 points Route DE Santa Fe to Las Vegas : 80 points Route DE Las Vegas to Los Angeles : 34 points Total DE DE DE DE l’Or points of interest: 384

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Routes POR Route 66 with Audio Guide

6 daysFree Cancellation

from $24

Per group

Likely to Sell Out

Explore the wonders of the Field Museum with general admission that covers all open general exhibitions, including the Griffin Halls of Evolving Planet & SUE the t. Rex. Enjoy unique access to the Grainger Hall of Gems and the engaging exhibit, Native Truths: Our Voices, Our Stories. As part of your ticket, select three tastings from a curated list featuring Field Museum Gin, Vodka, Rye, and Pseudo SUE Beer, all inspired by the museum's historic botanical collections. This experience is perfect for those 21 and older, combining education with a delightful tasting adventure.

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9100

Field Museum Basic Admission Ticket with Tasting Experience

4 to 5 hoursFree Cancellation

from $55

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Top Attractions in Chicago

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Chicago is known for its architecture and waterfront setting, and tours are an ideal way to explore the city's top attractions without the hassle of organizing your own itinerary. A variety of Chicago sightseeing tours are available—whether you prefer walking tours, bus rides, or boat cruises—all of which offer an efficient way to get to know the city with guides offering narration and insight. Tours typically include multiple stops, ranging from Millennium Park to the Chicago Riverwalk, Navy Pier, and Grant Park.

Top Chicago Sightseeing Tours - page 7

200+ results

Top Attractions in Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

Art Institute of Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

Art Institute of Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

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