Chicago Downtown Private Guided Walking Tour
Uncover Chicago’s bold spirit through its iconic landmarks, from the Gothic Holy Name Cathedral to the gleaming Cloud Gate. Hear untold stories of resilience, art, and innovation. Optional: see the Chicago Theatre, Cultural Center, and Tiffany glass dome.
Tour is available in following language:
English
French & Spanish
Choose one of our excellent tour options tailored to your needs and interests:
2-hour: Downtown
Visit Downtown Chicago to see landmarks like Holy Name Cathedral, Tribune Tower, and the Wrigley Building. Uncover stories of resilience and architectural beauty.
3-hour: Downtown, Chicago Theatre, & Cloud Gate
Visit Downtown Chicago and see the Chicago Theatre, Cultural Center’s Tiffany dome, and Cloud Gate. Extend your walk through rich history and iconic views.
This fun and history-filled tour will take you through the architectural wonders and cultural landmarks of Downtown Chicago. With a Licensed Private Guide, you'll uncover the stories behind iconic sites.
Private Cultural Walking Tour in Chicago with Lakefront Landmarks
This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public art reflects modern civic expression. What defines Chicago’s identity as a center of American innovation? Cloud Gate offers a striking reflection of skyline and sky. The DuSable Bridge stands as an engineering achievement tied to the city’s growth. Along the waterfront, Navy Pier reveals Chicago’s connection to commerce and recreation. This route connects cultural landmarks with the story of a city shaped by industry and design. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.
Bucktown and Wicker Park’s 606 Trail: A Walking Tour
The Bloomingdale Trail was built on a former railway line that once served as the industrial backbone of Chicago's north side. On this self-guided audio tour through Bucktown and Wicker Park, you'll hear how the factories, immigrants, and artists who lined these tracks transformed two scrappy neighbourhoods into some of the city's most sought-after real estate. The tour starts at Walsh Park, the eastern terminus of The 606, named with a nod to Chicago's universal zip code prefix. Further along, you'll stop at the Damen Avenue Arts Plaza, where the Flat Iron Arts Building stands as a reminder of how artists were deliberately recruited to revive a struggling neighbourhood. The tour ends at Western Avenue, the longest continuous city street in the world at 24.5 miles, where the trail continues west into Logan Square and Humboldt Park.
Daily Single Kayak Rentals Near Chicago
Looking for an unforgettable adventure that combines the thrill of paddling with the stunning natural beauty of Illinois? Our Guided Kayak Rentals near Chicago are the perfect way to experience Starved Rock State Park from a whole new perspective.
Chinatown Food Tour
Experience the authentic flavors of Chinatown on a 3-hour guided food tour curated by Chicago Tribune Good Eating Award winner Z.J. Tong. As you explore the neighborhood with a local guide, you'll sample regional Chinese specialties, discover the stories behind each dish, and gain a deeper understanding of Chinatown's rich culture and history. Tea and ice water are included throughout the tour.
- Sample authentic regional Chinese dishes at local favorite eateries.
- Explore Chinatown with knowledgeable guides connected to the community.
- Learn the cultural traditions and stories behind every tasting.
- Enjoy an award-winning culinary experience curated by Z.J. Tong.
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.
Offbeat Street Art Tour of Fulton Market and West Loop
Explore the vibrant art scene of Chicago on the Offbeat Street Art Tour through Fulton Market. This guided walking tour takes you into a neighborhood where industrial buildings have become canvases for stunning murals and installations. Discover the stories and cultural influences that define this area, once a meatpacking district, now a hotspot of creativity and innovation. Ideal for both locals and visitors, this tour provides a unique perspective on Chicago's urban culture, with numerous photo opportunities along the way.
- Guided walking tour through the artistic Fulton Market neighborhood
- Discover vibrant murals and thought-provoking installations
- Learn about the artists and cultural influences shaping the area
- Perfect for locals and visitors seeking a fresh view of Chicago
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
Chicago Field Museum Ticket and Audio Tour on Your Phone
• Skip the lines and explore the world-renowned Field Museum with a ticket and a digital tour - all in one app
• Get into an Ancient Egyptian tomb and learn incredible facts about mummification and death rituals
• Meet face-to-face with the largest predator that ever walked on Earth, SUE the Tyrannosaurus rex
• Follow billions of years of evolution to see the 3.2-million-year-old Lucy, the oldest human fossil
• Feel like on a wildlife-watching expedition walking along the Nature Walk amidst detailed dioramas
Private Transfer: Midway Airport MDW to Chicago by Luxury SUV
Reliable ground transportation from the airport
The modern traveler will appreciate the importance of a hassle-free journey from the airport. If you travel several times a year to distant destinations, you will be well aware of the individual and unique pitfalls and challenges that may await you on the way from the airport. With reliable airport transfers, you can experience the same high level of service wherever you go - a familiar feeling in an often unfamiliar environment. Your driver will meet you at the airport when you land, ready to help you carry your luggage to a waiting car and then take you smoothly and directly to your destination in the city.
A Remarkable Scavenger Hunt: The Great Quest in Illinois
Let’s Roam is the #1 app-led adventure hunt company! Embark on a journey to the best landmarks and hidden gems, answering trivia questions and tackling exciting challenges along the way. Team up with friends or compete against them as you uncover new facts and create unforgettable memories.
Let’s Roam Adventure Hunts are perfect for everyday fun, bachelorette parties, birthday celebrations, corporate team-building events, and more! Each player selects an interactive role, with challenges tailored just for them. Get ready for an adventure like no other!
Departure Private Transfer: Chicago to O'Hare Airport ORD in Business Car
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.
Cherry Valley Crusade Scavenger Hunt
Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment!
Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!
Fun Pasta Making Class With a Local Chef in Chicago
Forget complicated pasta projects — this is your excuse to make ridiculously cozy gnocchi from scratch. At a relaxed Chicago whiskey distillery, you’ll mix ricotta, flour and egg into a tender dough, then roll and cut it before shaping each piece by hand. You’ll pick up practical techniques for working with soft dough without overthinking every little move. Once your gnocchi is ready, you’ll cook it and make a rich sage butter sauce with Parmesan, fresh herbs and seasonal garnishes. You’ll learn how to combine the ingredients into a balanced, savory finish, then sit down to enjoy your freshly prepared meal. The atmosphere stays casual and social, making it easy to chat, laugh and enjoy the process. Your potatoes can take the night off — ricotta is handling gnocchi duty.
Chicago Riverwalk Architecture Walking Tour
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
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.
Astounding University Hunt: The Great Quest in Illinois
"Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration!
Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza.
Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll!
With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure!"
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.
Route 66 Multi Day Tour from Chicago to Los Angeles
Travel the legendary Route 66 in 14 unforgettable days - from Chicago to Los Angeles across eight states, discovering over 450 handpicked points of interest. Explore iconic landmarks, historic towns, scenic detours, hidden gems, classic diners, and breathtaking landscapes while creating your own version of America’s most famous road trip.
Podcast Tour Chicago The Promised Land and the Black Metropolis
Step into the vibrant, resilient heart of Chicago's South Side. On this immersive journey through Bronzeville, you will uncover the epic story of the Great Migration—a time when millions of African Americans fled the Jim Crow South to build a self-sustaining 'Black Metropolis'. From the birthplace of gospel music to the headquarters of a newspaper that changed the nation, discover the triumphs of entrepreneurship, the brilliance of cultural innovation, and the unyielding spirit of a community that shaped modern America.
A 3.9 km self-guided tour with 7 stops over 121 min
Ideal for travelers interested in Identity, Migration & Globalization and History & Memory
Immersively told in a podcast style by experts and locals
Matching audio content, AI guide and navigation through the app
Immersive Potsticker Cooking Class in Chicago
Chef Janet, a seasoned head chef, personal chef and culinary instructor, has served and educated countless food enthusiasts throughout her career. Let Chef Janet's expertise and charisma guide you in mastering the art of dumpling-making. This class takes place at a beautiful local venue known for its warm atmosphere and excellent craft beers. In this session, you'll start by preparing meat dumplings (vegetarian option available) using ingredients like carrots, cabbage, scallions, garlic, ginger and soy. You'll then create a tasty dipping sauce with soy and citrus. The class concludes with steaming or pan-frying your dumplings and enjoying your flavorful creations.
What to Expect:
- Step-by-step guidance from a talented chef who makes it make sense.
- A fun, beginner-friendly class where no one judges your knife skills.
- Tasting, laughing and leveling up your kitchen game.
- Ideal for: a solo outing, date night, girls’ night or group fun.
Murder Mystery Detective Experience in Skokie IL
Step into the shoes of a newly-minted detective, tasked by Commander Mahoney to solve a gripping case... murder on the streets of Skokie.
Throughout this crime-solving audio adventure, visit each of the 10 mapped locations. You'll have the option to explore the downtown area using the Walking Map or follow a Driving Map on the city's outskirts. Once you choose, the exact starting point will be revealed. *See images for route.
Park or stop at each location, listen to the audio story, and put your detective skills to the test by gathering clues and piecing together the evidence. Finally, make your deductions and issue an arrest warrant.
Your overall detective skills will be evaluated, culminating in a Case Performance Score to measure your sleuthing prowess. This game is suitable for solo detectives, dynamic duos, or groups of mystery enthusiasts, offering an immersive audio tale filled with intrigue.
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.
