Chicago
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Viator
Chicago Gangsters and Prohibition Private History Tour
Discover Chicago’s infamous gangster past on a private, fully personalized tour through the city’s historic Prohibition-era streets. Travel in comfort with your English-speaking driver, who shares captivating stories about Al Capone, rival gangs, speakeasies, and legendary crime events of the 1920s and 1930s. Begin at Biograph Theater, where John Dillinger was shot, then visit the St. Valentine’s Day Massacre site, a pivotal moment in Al Capone’s rise. Explore Holy Name Cathedral, the Cook County Criminal Court Building, and Harry Caray’s Italian Steakhouse, all linked to Chicago’s mob history. Conclude in the Chicago Loop, uncovering hidden speakeasies and secret nightlife spots from the Prohibition era. With a flexible, door-to-door itinerary, this private tour offers an immersive, thrilling look into the city’s dramatic gangster history.
2.3(3)
2 Hours
Chicago
- Free cancellation
- Private tour
- New
From
$115
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Viator
Discover Chicago: A Self-Guided Walking Tour
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.
2.0(1)
8h 30m
Chicago
- Free cancellation
- Private tour
- New
From
$9
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Viator
Chicago River Yoga Walk Tour
This is truly an experience like none other. It is combination of a historical walking tour of the Chicago Riverwalk and Yoga. It is a very non-traditional Yoga experience as we incorporate flows along the walking tour, in picturesque locations with beautiful views. No mats are necessary as we incorporate the surrounding elements of the Riverwalk, ie: benches, steps, and grassy lawns. A Fit Tour is the most unique way to "get your steps in" and actively engage with the surrounding city.
1h 30m
Chicago
- Free cancellation
- Likely to sell out
From
$44
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Viator
Private One-Way Airport Transfer from O'Hare Airport to Chicago
We understand the importance of ensuring a hassle-free transfer experience. Our private airport transfer service allows you just that. Book our private airport transfer service and enjoy a safe, reliable, comfortable, and convenient journey from O'Hare International Airport (ORD) to your accommodation in Chicago. Let us take care of your transportation needs, allowing you to focus on enjoying your trip to the fullest.
45 Minutes
Chicago
- Free cancellation
- Private tour
From
$94
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Viator
Great Smoky Mountains,Gatlinburg 4-Day Tour from Chicago
1. Explore Motorsports Hall of Fame. 2. Be in the National Park with most visitors in US -- Great Smoky Mountains. 3. Southern dinner show Dixie Stampede featuring America’s civil war. 4. Tour in Lookout Mountain: Rock City, Ruby Falls, Incline Railway. Room Details All hotel rooms are based on two Full / Double beds or one King/Queen bed depends on what rooms are availiable at the hotel on the day. The maximum occupancy per room is four travelers. One Room Selection If you are a party of more than four guests or desire to have separate rooms, please create separate bookings. Avoid traveling in a different bus? If you have more than one booking, please provide all confirmation numbers once your bookings are complete.
4 Days
Chicago
- Free cancellation
From
$1,030
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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
Chicago O`Hare Airport (ORD) to Chicago: Arrival Private Transfer
Book your private arrival transfer from Chicago O`Hare Airport (ORD) to Chicago. Avoid the hassle of waiting in long taxi or shared shuttle queues and use our private, door-to-door airport transfer. Your driver will be waiting for you at the scheduled time, and you can travel comfortably to your destination. We track your flight. Our driver greets you with a name plate. We provide door-to-door service. There are no hidden charges. We use clean cars and professional drivers.
30 Minutes
Chicago
- Free cancellation
- Private tour
From
$102
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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
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Viator
Latin Libations Mixology Experience
Unlike typical cocktail classes, this experience is infused with culture, storytelling, and hospitality rooted in Latin and Caribbean traditions. Hosted by Chef & Mixologist Inez Melendez at the warm, welcoming Chicago Mama’s Kitchen, you’ll learn more than just how to mix a drink—you’ll explore the origins of ingredients, the legacy of spirits like rum and agave, and the personal stories behind each cocktail. This is a true culinary journey in a glass—designed to connect people through flavor, rhythm, and shared experience. With small group sizes, hands-on participation, and a fun, relaxed vibe, it’s not just a class—it’s a celebration.
1h 30m
Chicago
- Free cancellation
- New
From
$100
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Viator
Chicago Riverwalk Architecture Walking Tour and Discover Skyline
Explore Chicago's iconic skyline on this enlightening Riverwalk architectural tour. Experience the rich tapestry of history and innovation as "you get your steps in" along the scenic Riverwalk, revealing the stories behind the city’s most celebrated structures. Expert guides will share insights into the work of renowned architects like Mies van der Rohe and Jeanne Gang, showcasing the stunning interplay of glass, steel, and water. Ideal for architecture enthusiasts and first-time visitors alike, this tour offers a unique perspective on the Windy City’s vibrant culture and architectural beauty. - Discover Chicago’s architectural evolution from Art Deco to modern designs - Guided insights from experts on legendary architects and their masterpieces - Enjoy a scenic stroll along the picturesque Riverwalk - Perfect for both architecture lovers and those new to Chicago
1h 30m
Chicago
- Free cancellation
From
$49
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Viator
Chicago O`Hare Airport (ORD) to Chicago: Round-Trip Transfer
Book your private transfer from Chicago O`Hare Airport (ORD) to Chicago and return. Avoid the hassle of waiting in long taxi or shared shuttle queues and use our private, door-to-door airport transfer. Your driver will be waiting for you at the scheduled time, and you can travel comfortably to your destination. • We track your flight. • Our driver greets you with a name plate. • We provide door-to-door service. • There are no hidden charges. • We use clean cars and professional drivers.
1 Hour
Chicago
- Free cancellation
- Private tour
From
$204
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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
2 Hour Pullman/Roseland Chicago Tour
Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Pullman, led by Historian Dilla, who uncovers the unique stories and contributions of these communities, providing an authentic experience of Chicago's diverse heritage. Whether you're a history buff or simply curious about local culture, these tours offer fascinating insights into the Windy City's past and present. The tours vary in duration but typically last around 2 hours, making them perfect for a quick but enriching adventure. - Discover the history and culture of Chicago's neighborhoods - Tours available in Pullman - Led by knowledgeable Historian Dilla for an authentic experience
2 Hours
Chicago
- Free cancellation
- New
From
$45
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Viator
Chicago Bears Football Game at Soldier Field
One of the two remaining founding members of the NFL, dating back to 1920, the Chicago Bears are the epitomise NFL history. For an experience filled with tradition and history, look no further than attending a Bears game at the iconic Soldier Field. The Bears are entering a new era, led by former Heisman-Trophy winning quarterback, Caleb Williams. The excitement and electricity in the air Solider Field is noticeable and expectations amongst the Bears passionate fanbase have been raised. Soldier Field, the oldest stadium in the NFL, is a historic venue, located on the shores of Lake Michigan, with a unique architectural blend of the original structure and modern upgrades. The tailgating scene at Soldier Field is vibrant. Fans gather hours before the game to socialize and celebrate, forming a big part of the game day experience. Attending a game is also an opportunity to explore the city, known for its famous deep-dish pizza, you’ll have to get a taste of the real Chicago culture!
4 Hours
Chicago
- New
From
$436
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Viator
Chicago Airport Luggage Services Same-Day Delivery and Storage
Unlike other providers that only offer storage, uniquely combines both storage and delivery services. Let your bags picked up curbside at the airport, securely stored at our facility, and delivered to their hotel all on the same day in time for check-in. We are the only service in Chicago offering this convenient, all-in-one solution.
30 Minutes
Chicago
- Free cancellation
- Private tour
From
$99
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Viator
Departure Transfer: Chicago to O'Hare Airport ORD by Luxury SUV
Your safety is our crew’s biggest priority. Before your journey even begins, your chauffeur completely disinfects the vehicle and places free hand sanitizer in the back seat. One of our professionally-trained drivers will greet you with a name sign in the reception of the hotel, will offer to assist with luggage and guide you to your vehicle. Your driver will open and close the door for you, and for your safety, guests are only permitted to ride in the back seat. We’re here to ensure you arrive at your destination feeling healthy, happy, and ready to take your flight.
30 Minutes
Chicago
- Free cancellation
- Private tour
From
$220
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Viator
Chicago to Mackinac Island Scenic Tour
Explore the charm of Mackinac Island on this delightful journey from Chicago. Experience a blend of history, culture, and stunning landscapes as you travel through the Great Lakes region. Discover the island's unique features, where cars are absent, allowing horse-drawn carriages to roam freely among Victorian architecture and beautiful scenery. Enjoy iconic sites like Fort Mackinac and Arch Rock while wandering through quaint downtown shops and savoring famous fudge. This tour is designed for families, couples, and solo travelers looking for a serene getaway filled with natural beauty and cultural richness. - Scenic travel through the picturesque Great Lakes region - Discover Mackinac Island's charm without car traffic - Visit Fort Mackinac, Arch Rock, and local boutiques - Ideal for families, couples, and solo adventurers seeking relaxation
16 Hours - 17 Hours
Chicago
- Free cancellation
- New
From
$795
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Viator
Chicago Private Tour
Enjoy and appreciate Chicago with your private transportation and guide. Customize your tour and visit the most important sites and landmarks of the Windy City. Be satisfied that you experienced the most important and beautiful sites, taking the most memorable tour of the city.
3 Hours
Chicago
- Free cancellation
- Private tour
From
$300
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Viator
Midway Airport Transfer to Chicago by Sedan - Meet & Greet inside
Inside Greet and Meet With Luggage Assistance. A professional, uniformed driver will pick you up at Chicago Midway Airport, Meet you inside the Airport (Lower Level, baggage claim) holding a sign with your name on it. He will help you with the luggage and guide you to your limousine. Skip the stress of a taxi or shared shuttle between Midway Airport and Chicago downtown with the Highest rated limousine service in Chicago on Trip Advisor, Google and Yelp. Travel in a comfortable, newer private sedan for a safe and relaxed ride. All our drivers are licensed and insured and all our sedans carry a $350,000 insurance policy. Ensure a hassle-free arrival at your Chicago Downtown hotel with this private transfer service.
Chicago
- Free cancellation
- Private tour
From
$133
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Viator
O’Hare-Midway to Downtown Chicago: Stretch Limousine
Luxurious Fleet: Our fleet consists of top-of-the-line luxury vehicles, meticulously maintained to provide the utmost comfort and style during your journey. Whether you're traveling solo, with a group, or for a special occasion, we have the perfect vehicle to suit your needs. Professional Drivers: Our drivers are not only highly skilled behind the wheel but also epitomize professionalism and courtesy. They prioritize your safety and satisfaction, ensuring a smooth and enjoyable ride from pick-up to drop-off. Affordable Rates: Despite offering top-notch service and luxurious vehicles, we believe in providing affordable rates to our customers. Enjoy the luxury and convenience of private transportation without breaking the bank. With transparent pricing and no hidden fees, you'll know exactly what to expect when you book with us. Flexible Booking Options: We offer flexible booking options to accommodate your schedule and preferences.
1 Hour - 1h 30m
Chicago
- Private tour
- New
From
$385
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Viator
Private Tour Art Institute of Chicago Guided Museum
Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to the heart of the city. Upon your arrival, meet your seasoned tour guide, ready to lead you on an enchanting tour of Art Institute of Chicago. Discover the awe-inspiring allure of Art Institute of Chicago, marvel at the grandeur of Chicago, and capture iconic moments and many more. Leave the details to us as we escort you on an extraordinary adventure, crafting memories that will stand the test of time!
5 Hours
Chicago
- Private tour
From
$1,068
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Viator
Michigan Avenue Rendezvous GPS App Walking Tour Mobile Game
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.
1 Hour - 2 Hours
Chicago
- Free cancellation
- Private tour
From
$17
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Viator
Executive Airport transfer SUV
Ryde Luxury Limousine is the trusted provider for thousands of clients. We provide the best in luxury transportation with affordable rates, professional and friendly chauffeurs, safe and comfortable vehicles, and a focus on customer service. Our limo service in the city of Chicago is the top choice if you need airport transportation, want a special night out, going sightseeing in the beautiful windy city, or need daily business transportation. Our limo services get you to your destination safely, efficiently, and comfortably.
50 Minutes
Chicago
- Free cancellation
- Private tour
From
$180
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Viator
Roll, Fold & Feast: An Empanada Making Experience
Transform your gatherings into memorable culinary celebrations with Chicago Mama’s Kitchen. Specializing in Puerto Rican cuisine, we offer immersive mixology and cooking workshops tailored to any occasion, from intimate dinners to corporate events. Delight in crafting hand-made empanadas and refreshing cocktails with expert guidance, ensuring a fun and flavorful experience for all. Perfect for birthdays, team-building, or just a fun night in, your workshops can accommodate groups of up to 50. Bring the vibrant flavors of Puerto Rico to your home or office and savor an unforgettable culinary journey. At Chicago Mama’s Kitchen, guests dive into hands-on culinary and mixology experiences that celebrate Latin flavors with a Chicago twist. Led by Chef Inez Melendez, each class blends culture, creativity, and community—teaching authentic recipes, craft cocktails, and heartfelt hospitality in a warm, communal kitchen setting.
1h 30m
Chicago
- Free cancellation
- New
From
$80
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