Chicago
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2 hours Private Evening Walking Tour with the Ghosts of Chicago
Step into the eerie past of Chicago on this thrilling 2-hour private ghost tour led by a local through the haunted corners of the Lincoln Park area.
2 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$350
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Viator
Chicago Self-Guided Walking Audio Tour
Relive this city’s most remarkable historic events while visiting the towering buildings, fascinating sculptures, and beloved public spaces built by generations of Chicago laborers who brought to life the ingenious ideas of some of the world’s most influential designers.
1 Hour - 2 Hours
Chicago
- Private tour
- New
From
$5
No similar experiences found
Viator
Private 2-Hour Walking Tour: Chicago Loop Interior Architecture
Make the best of your visit to Chicago and explore the interiors of the emblematic Loop of Chicago downtown with a private licensed guide. You will enjoy a private tour and discover the hidden architectural treasures of Chicago with a local expert. Here are some examples of what you will enjoy: - Chicago Loop, Chicago - Chicago Cultural Center - Untitled by Picasso, - Block 37, - Marshall Field's Wholesale Store, This is a private tour just for your group.
2 Hours
Chicago
- Private tour
From
$322
No similar experiences found
Viator
Routes POR Route 66 with Audio Guide
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
6 Days
Chicago
- Free cancellation
- Private tour
From
$24
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Viator
Chicago Downtown Walking Tour & Lake Michigan Cruise Tickets
Walk beneath Chicago’s soaring skyline, hear its hidden stories, then see it shimmer from the water on a lake cruise. From the iconic Bean to the legendary theatre district, this tour brings the city’s spirit to life—one step and wave at a time. Highlights: • Discover downtown Chicago on foot with a 5-Star Private Guide leading the way • Cruise Lake Michigan with included tickets and audio commentary onboard • See breathtaking skyline views and snap iconic photos from the water • Learn the city’s best-kept secrets through fascinating stories and history • Get tailored recommendations on top spots to eat, visit, and explore next Did you know there’s a sculpture in Chicago that reflects the whole skyline? With Rosotravel’s private tour, you'll walk through the city’s most iconic spots, then see it all again from the water on a relaxing lake cruise. It's a fun, personal way to experience the best of Chicago in just a few hours.Reserve your spot ow!
3 Hours
Chicago
- Free cancellation
- Private tour
From
$263
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Viator
Skyline, Lakefront and Millennium Park Chicago Private Day Tour
Explore Chicago’s iconic landmarks and scenic lakefront on a private, fully personalized city tour. Travel in comfort with your English-speaking driver, who shares local stories, history, and insights while guiding you through the city’s most famous sites. Begin at Millennium Park to see the iconic Cloud Gate sculpture (“The Bean”), then visit Buckingham Fountain in Grant Park for stunning lake and skyline views. Drive through downtown to admire the Willis Tower Skydeck area, then enjoy the Chicago Riverwalk and Wacker Drive for striking architectural vistas. Continue to Navy Pier with its attractions and Centennial Wheel, then take a scenic drive along Lake Shore Drive for panoramic lakefront skyline views. Conclude at Lincoln Park and North Avenue Beach for one of the city’s most memorable photo spots. This flexible, door-to-door private tour offers a relaxed and immersive way to experience Chicago’s architecture, waterfront, and vibrant urban culture.
3 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$171
No similar experiences found
Viator
Chicago Private Lakefront Sunset and Skyline Photo Tour
Enjoy a private, fully personalized sunset tour along Chicago’s scenic lakefront. Travel in comfort with your English-speaking driver, who shares insights into the city’s architecture, skyline, and history while guiding you to the best photo spots. Begin at Museum Campus, where the skyline rises above Lake Michigan, offering stunning reflections at golden hour. Continue to Adler Planetarium for one of Chicago’s most iconic panoramic skyline views. Visit Buckingham Fountain, where the historic landmark creates a beautiful foreground for sunset photos. Head to North Avenue Beach to capture the skyline stretching across the horizon as the sun sets, then enjoy a scenic drive along Lake Shore Drive as city lights begin to glow. With a flexible itinerary and door-to-door service, this experience offers a relaxed, unforgettable way to capture Chicago’s skyline from day to night.
2 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$144
No similar experiences found
Viator
Private Shopping Tour from Chicago to Chicago Premium Outlets
Comfortable Roundtrip Tour from your hotel in Chicago to Chicago Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.
5 Hours - 6 Hours
Chicago
- Free cancellation
- Private tour
From
$294
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Viator
Hyde Park Walking Tour History Race and Urban Change
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
3 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$5
No similar experiences found
Viator
Private Architectural Walking Tour in Chicago Loop Landmarks
Skip the crowds this is a private tour for your group only! Embark on a captivating journey through the Loop’s architectural wonders with our Loop Architecture Tour in Chicago. Explore the iconic Chicago Board of Trade Building and the historic Rookery Building, steeped in timeless elegance. Marvel at the striking Calder sculpture in Federal Plaza, a highlight of the city’s public art scene. Admire the innovative design of the Marquette Building, a masterpiece of the Chicago School of Architecture. Step into the luxurious Palmer House, a landmark boasting historical significance. Discover the rich legacy of the Marshall Field and Company Building, a symbol of Chicago’s commercial prowess. Finally, delve into the cultural richness of the Chicago Cultural Center, showcasing the city’s artistic diversity. Join us on this unforgettable journey through Chicago’s architectural gems in the heart of the Loop.
2 Hours
Chicago
- Free cancellation
- Private tour
From
$869
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Viator
Bizarre Wicker Park: Medicine and Mobsters Self-Guided Audio Tour
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.
45 Minutes - 1h 15m
Chicago
- Free cancellation
- Private tour
- New
From
$10
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Viator
Logan Square Walking Tour Experience
An amazing, local's guided tour of one of Chicago's coolest neighborhoods. Learn the history and get advice from a local who knows this area and make your Chicago experience a memorable one. Get out of downtown, come and experience the neighborhoods that make Chicago the great city that it is. Looking forward to seeing you!
1h 20m
Chicago
- Free cancellation
- Private tour
- New
From
$35
No similar experiences found
![Downtown Chicago City Tour In a Lamborghini[60 Minute Experience]](/_next/image?url=https%3A%2F%2Fmedia-cdn.tripadvisor.com%2Fmedia%2Fattractions-splice-spp-480x320%2F17%2F05%2F8d%2Fda.jpg&w=3840&q=75)
Viator
Downtown Chicago City Tour In a Lamborghini[60 Minute Experience]
Experience Chicago in unparalleled style with a 10-mile cruise through the city in a luxury or exotic vehicle. Glide through iconic streets, turning heads at every stop, while taking in the captivating sights of the Windy City. Whether you're a resident or visitor, this exclusive ride offers a fresh perspective of Chicago's vibrant energy and charm. Don’t miss the chance to explore the city like never before—reserve your adventure and drive through Chicago’s heart in true sophistication. All tour vehicles are subject to availability During This Ride You May See Views Of The Following Land Marks: Little Italy Willis Tower Harold Washington Library The Chicago Theatre Millennium Park Grant Park Buckingham Fountain Magnificent Mile Gold Coast Museum of Science & Industry Lake Michigan And much more! We cannot guarantee that all sites on this list will be seen in your tour.
45 Minutes - 1 Hour
Chicago
- Private tour
- New
From
$99
No similar experiences found
Viator
Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour
See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the footsteps of the gangsters, bootleggers, hoodlums, gunmen, and crooked cops and politicians who made up what was known as the “Chicago Outfit” • Hear from producer Richard Junger, an urban historian, professor and author passionate about Chicago • Do it all in 45 minutes or linger at stops along the way with complete control over when you start and finish • Get unlimited use before your booking date and after it • Use the virtual tour option at home Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the VoiceMap app and enter your code. The app displays directions to the starting point, and when you’re in the right place, just pop in your headphones and tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.
45 Minutes - 1 Hour
Chicago
- Private tour
From
$7
No similar experiences found
Viator
4 Hours of Chicago City Tour Sedan
Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city
4 Hours
Chicago
- Free cancellation
- Private tour
From
$640
No similar experiences found
Viator
Resilience and Revolution: Audio Tour of Chicago’s Black History
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.
2 Hours - 2h 30m
Chicago
- Free cancellation
- Private tour
- New
From
$15
No similar experiences found
Viator
Chicago Willis Tower Skydeck Ticket and Audio Tour with City Walk
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
2 Hours
Chicago
- Private tour
- New
From
$79
No similar experiences found
Viator
Chicago Jewish History Landmarks Private Guided Walking Tour
Walk through Chicago’s vibrant Jewish history, from the striking Loop Synagogue to the inspiring Heald Square Monument and Jay Pritzker Pavilion. Uncover hidden gems and untold stories that shaped the city’s cultural heart. Book your journey today! Tour is available in following language: English Spanish & French Highlights: • Explore Chicago’s Jewish heritage with a knowledgeable 5-Star Private Guide • Discover key Jewish landmarks and skip common tourist routes with ease • See historic monuments and hidden gems that shaped the city’s vibrant culture • Learn inspiring stories of Jewish contributions to Chicago’s art and history • Get custom tips for more cultural sites and experiences around the city Follow the footprints of Jewish history through Chicago’s vibrant streets!. On this private walking tour with Rosotravel, a Licensed Guide will tailor the experience to your interests, revealing hidden gems, fascinating stories, and historical treasures.
2 Hours
Chicago
- Free cancellation
- Private tour
From
$227
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Viator
Skip-the-Line Art Institute of Chicago Private Guided Tour
Skip the lines to the iconic Art Institute of Chicago and marvel at world-famous masterpieces by Monet, Van Gogh, and Picasso. Dive into a treasure trove of art, history, and culture at one of the oldest and most celebrated museums in the U.S. Tour is available in following language: English Spanish & French Highlights: • Private Tour of the Art Institute of Chicago • 5-Star Licensed Guide fluent in your chosen language • Skip-the-Line Tickets to the Art Institute of Chicago • Insightful stories about world-famous masterpieces, including works by Monet, Van Gogh, and Picasso • Expert guidance through Impressionist, Post-Impressionist, and Modern Art collections Discover the rich art and cultural heritage of Chicago with Rosotravel on an exclusive private tour with Skip-the-Line Tickets to the iconic Art Institute. Enjoy the luxury of a personalized itinerary led by a Licensed Private Guide. Uncover the magic of Chicago’s artistic treasures today!
2 Hours
Chicago
- Free cancellation
- Private tour
From
$318
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Viator
Chicago Sports Legends Guided Tour
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
2 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$5
No similar experiences found
Viator
Pilsen Chicago Walking Tour: Street Art & Mexican History
Discover Pilsen, one of Chicago’s most vibrant neighborhoods, known for its colorful street art, rich Mexican heritage, historic architecture, and thriving local culture. This locally led Pilsen walking tour offers an authentic, insider experience beyond typical Chicago sightseeing. - Pilsen-based experts with 40+ years of combined experience - Explore iconic sites like 16th Street murals, Thalia Hall, and local cultural landmarks - Official Pilsen tour partner of the Chicago History Museum - Bilingual tours available in English and Spanish - Multiple routes and flexible options, including walking, running, or biking tours
1h 15m
Chicago
- Free cancellation
- Private tour
- New
From
$35
No similar experiences found
Viator
Private Historical Ghost Walking Tour in Chicago Lincoln Park
This private historical ghost walking tour in Chicago explores stories rooted in the city’s layered past. You will walk through Lincoln Park, an area shaped by transformation from cemetery grounds to residential district. What traces of earlier history remain beneath modern streets? Architectural landmarks reflect 19th-century development and urban expansion. Historic venues such as theaters and pubs carry narratives passed through generations. These accounts reveal how memory and place intertwine within the city’s cultural fabric. The experience offers a thoughtful perspective on Chicago’s past through legend and documented history. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.
2 Hours
Chicago
- Free cancellation
- Private tour
From
$869
No similar experiences found
Viator
Sip Happens: Chicago Loop Prohibition Tour
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
1h 30m - 2 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$5
No similar experiences found
Viator
Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle
Explore the surprising beauty and history of the Windy City with this combo tour of Chicago’s Millennium Park and Riverwalk! Snap a picture by the famous Cloud Gate sculpture and get away from the hustle and bustle in the city’s most iconic park. Then, stroll along the picturesque riverside, admire Chicago’s totally unique architecture, and learn the fascinating stories behind the city’s skyline. This combo is the easiest, best way to get to know this complex city! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.
1 Hour - 2 Hours
Chicago
- Free cancellation
- Private tour
From
$25
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