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.
Duration: 2 hours
- Free cancellation
- Private tour
Chicago Architecture Walking Tour: What's New
Over the course of 90 minutes, explore some of the newest buildings around the Chicago Architecture Center, focusing on construction elements and their impact on the city’s built environment.
What's New looks at some of the most recent additions to the built environment surrounding the Chicago Architecture Center. This walking tour focuses on each building's height, structure, materials, ornament and its impact on the environment, the neighborhood and the city's economy. The tour showcases several recently completed buildings, including 462 N. Park and the St. Regis, and compares them to each other in order to observe emerging patterns. These new additions are also contrasted with some of the older buildings downtown as a way to highlight developments.
As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.
Duration: 1 hr 30 min
- Free cancellation
Private Wicker Park and Bucktown Walking Tour
This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time to see a whole different side of the city.
The tour has 2 options:
Wicker Park and Bucktown - faster pace, 2.5 miles of walking.
Wicker Park only - slower pace, 1.5 miles of walking
Duration: 2 hr 30 min
- Free cancellation
- Private tour
Private One-Way Airport Transfer From Chicago To O'Hare Airport
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 your accommodation in Chicago to O'Hare International Airport (ORD). Let us take care of your transportation needs, allowing you to focus on enjoying your trip to the fullest.
Duration: 45 min
- Free cancellation
- Private tour
Chicago Private Neighborhoods Tour to Lincoln and Hyde Park
Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares local stories, historical insights, and highlights the architecture and communities that shape the city’s unique character.
Begin in the Gold Coast Historic District with its elegant mansions and tree-lined streets, then explore Lincoln Park with its scenic paths, gardens, and historic zoo. Visit Wrigley Field to experience Chicago’s sports culture, followed by Hyde Park and the University of Chicago, known for its stunning architecture and intellectual heritage.
Conclude in Chinatown, a lively cultural district with colorful streets, markets, and traditional restaurants. With a flexible, door-to-door itinerary, this private tour offers a relaxed, immersive way to experience Chicago’s history, culture, and diverse neighborhoods.
Duration: 4 hours
- Free cancellation
- Private tour
Midway Airport Transfer to Chicago by Luxury SUV - Inside Meet
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 vehicles 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.
- Free cancellation
- Private tour
Chicago Walking Tour: Historic Skyscrapers
Chicago is home to some of the world’s earliest skyscrapers. Get an up-close look at these 19th Century marvels, learn about innovations used to build them and discover how they transformed Chicago into a center of skyscraper design and engineering.
Highlights on this walking tour include Burnham and Root’s Rookery (1888), a transitional building with a Moorish and Romanesque exterior and a stunning interior atrium re-designed by Frank Lloyd Wright; Adler and Sullivan’s Auditorium Building (1889), a masterpiece of acoustical and structural engineering; and Holabird and Roche’s Marquette Building (1895), an outstanding example of the metal frame expression with traditional details and decorations.
As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.
Duration: 1 hr 30 min
- Free cancellation
Sushi Making Cooking Class at a Local Distillery in Chicago
Enjoy a unique sushi-making experience at a local distillery in Chicago with Chef Janet! In this hands-on class, you’ll learn how to craft fresh, restaurant-quality sushi while sipping on expertly distilled spirits available for purchase. Start by steaming and seasoning the perfect sushi rice, then prep fresh ingredients for two signature rolls. You’ll assemble a vibrant veggie roll with sweet mango, creamy avocado, and crisp cucumber, followed by a classic California roll featuring surimi, avocado, and cucumber. With Chef Janet’s expert guidance, you’ll master the techniques of rolling sushi and slicing it into picture-perfect pieces. Whether you're looking for a fun night out, a unique date idea, or a new culinary skill to impress friends and family, this class offers the perfect blend of great food, hands-on learning, and a relaxed distillery setting. Book your spot today for a sushi and spirits experience like no other in Chicago!
Duration: 2 hours
- Likely to sell out
- Free cancellation
One Day Galena and Dubuque Tour from Chicago
Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, where you can enjoy free time to stroll, have lunch, or even take a cable car ride for breathtaking views. Continue to Galena, a beautifully preserved historic town where 80% of the buildings are listed on the National Register of Historic Places. Here, you’ll visit the Ulysses S. Grant Home and take in the serene beauty of Grant Park. With a total travel distance of 325 km from Chicago, this tour offers the perfect blend of history, scenery, and relaxation before heading back to the city.
Duration: 9–10 hours
- Free cancellation
O’Hare-Midway to Downtown Chicago: Stretch Limousine
THE LINCOLN MKT STRETCH LIMOUSINE OFFERS SEATING FOR 8 PASSENGERS, WITH LUGGAGE CAPACITY FOR 3 CHECKED-IN BAGS AND 3 CARRY-ON ITEMS.
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.
Duration: 1 hour – 1 hr 30 min
- Free cancellation
- Private tour
Cooking Class with Celebrity Chef Tony Hu
Join our exclusive cooking workshop series in collaboration with celebrity chef Tony Hu. In the first session, you'll learn to prepare two of his signature dishes—Chef’s Special Dry Chili Chicken and Crispy Lemon Shrimp.
Featured on numerous TV shows and interviews, including NBC, ABC, FOX, and WGN, Chef Tony Hu is the founder of the iconic Lao Sze Chuan Restaurants with 14 locations across the country. This hands-on cooking workshop is more than just a culinary lesson—it’s a cultural experience. We invite you to connect with Chinese heritage in a warm, interactive setting where every dish tells a story, and every bite is a celebration of tradition.
A minimum of 4 participants is required for this experience. If the minimum is not met, the tour may be canceled, and you will receive a full refund.
Duration: 1 hr 30 min
- Likely to sell out
- Free cancellation
SUV O'Hare/Midway Airport (Curbside) Chicago One Way
THE STANDARD SUV OFFERS SEATING FOR 5 PASSENGERS, WITH LUGGAGE CAPACITY FOR 3 CHECKED-IN BAGS AND 2 CARRY-ON ITEMS.
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.
Duration: 30 min – 1 hour
- Free cancellation
- Private tour
Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago
Roam the lively heart of Lincoln Square with its cafés, delis, and other fun and fascinating stores; stand beside the Berlin Wall; take in ghastly history, gorgeous murals, and 300-year-old oak trees; and, at your journey’s end, find yourself rewarded by the sight of an architectural gem.
As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. Join the game!
Highlights include:
• Explore Merz Apothecary, Gene's Sausage Shop and Delicatessen, Lincoln Square Mural and lesser-known places.
• Enjoy a uniquely crafted story brought to you by our top-notch/gifted/talented writers.
• Try a new type of experience, the perfect mix between a tour, outdoor escape game, and treasure hunt.
After your booking you will receive an email with instructions on how to download and play the game on your phone. We recommend that each user purchases a ticket for an optimal experience, although several people can share a phone.
Duration: 1 hr 50 min – 2 hr 20 min
- Free cancellation
- Private tour
Private SUV Transfer from O'Hare Midway Airport to Chicago
Whether you're flying in for business or leisure, We ensures your journey is as smooth and stylish as your destination. Here's why travelers trust us:
Luxury Fleet for Every Occasion
Choose from executive sedans, SUVs, Sprinter vans, and minibuses
Immaculately maintained, climate-controlled, and equipped with premium amenities
Punctual & Reliable
Real-time flight tracking ensures on-time pickups—even if your flight is early or delayed
Chauffeurs arrive early and plan routes to avoid traffic delays
Professional Chauffeurs
Courteous, licensed, and experienced drivers
Dressed professionally and trained in customer service and safety
Easy Booking & Real-Time Updates
Book online in minutes with instant confirmation
Receive driver details and live tracking before your ride
Perfect for Business & Leisure
Ideal for corporate travel, family vacations, weddings, and group events
Discreet, comfortable, and tailored to your needs
Duration: 1 hour
- Free cancellation
- Private tour
2-Hour Chicago's Chinatown History and Culture Tour
Discover the heart of Chicago’s Chinatown with your authentic history and culture tours, exclusively offered by the official Chinatown Visitor Center. Led by experienced local guides, your tours dives deep into the neighborhood’s rich heritage, hidden landmarks, and cultural traditions. Unlike generic tours, we bring you behind the scenes with insider stories, community connections, and exclusive access to local favorites. Experience Chinatown through the eyes of those who know it best.
A minimum of 2 participants is required for this experience. If the minimum is not met, the tour may be canceled, and you will receive a full refund.
Duration: 2 hours
- Free cancellation
Haunted Chicago: Lincoln Park Ghost & History Walking Tour
This isn’t just a ghost tour, it’s a story-driven walk through one of Chicago’s most haunted landscapes, where real history and local legend collide.
Unlike tours that rely purely on jump scares or folklore, this experience is rooted in true events—from the forgotten cemetery beneath Lincoln Park to the devastating fires, disasters, and tragedies that shaped the city. Each stop connects documented history with reported paranormal activity, giving the stories weight, context, and credibility.
Set entirely within Lincoln Park, one of the most beautiful areas in Chicago, the contrast is part of what makes it unforgettable: you’ll walk through scenic paths and peaceful views while uncovering the dark past hidden just beneath your feet.
A blend of storytelling, humor, and atmosphere, this tour feels less like a lecture, and more like stepping into Chicago’s past as it quietly comes back to life around you.
Duration: 1 hr 30 min
- Free cancellation
History of the Jazz Age at Chicago Art Deco Architecture Tour
Dive into the center of the architectural boom of the roaring 1920s and take a chance to enjoy the grand facades of the Art Deco skyscrapers on this guided walking tour.
Go back in history while admiring one of the epicenters of the style’s birth. Immerse yourself into the life of the Windy City between World War I and World War II, the time when the design evolved and turned into neo archaic Mesoamerican grandeur, which can’t leave anyone indifferent. Be delighted with the variety of decorations and geometrical shapes which distinguish Art-Deco from Neoclassicism.
Uncover the stories behind the famous Loop district of Chicago. Delve into the atmosphere of the 1920s as you listen to more insights and facts from your enthusiastic local guide. Overview the history and pay attention to the details you wouldn’t notice without a tour. Grab the chance to get inside famous buildings and revel in the Art Deco interiors.
Duration: 1 hr 30 min
- Free cancellation
Private Luxury 6-Pax SUV Limo Transfer from or to Chicagoland Airport and Suburb
Enjoy convenient private transportation between Midway or O'Hare International Airport and your hotel in the comfort of a private 4 door 6 Passenger Luxury SUV Limousine. Airport or hotel transfer Multiple times offered throughout the day.
Duration: 30 min
- Free cancellation
Chicago 4-Hour Sightseeing Transfer by Luxury SUV
Skip the crowded, shared bus and enjoy the city from your own luxury vehicle and private, uniformed chauffeur. Stop where you want, when you want, stay as long as you like.
Full Tour Customization - Choose your own route, attractions & timeline!
Experience Chicago from your own luxury private vehicle driven by professional chauffeurs. We can accommodate any request, just ask!
- Chicago's Highest Rated Limo And Car Service
- 10 Years in the limousine business
- Proven track of exceptional customer service
- Professional, Safe, Fully Uniformed Chauffeurs
- FBI Background checks for all drivers
- $350,000 Commercially Insured
- GPS tracking devices on all vehicles
- "Driver ON Location" automated text message
- Chicago Based company
Note: This service includes private transportation only. No tour guide or narration is provided
- Free cancellation
- Private tour
Downtown Chicago Loop Walking Tour (Private)
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.
Duration: 2 hours
- Free cancellation
- Private tour
Chicago and All MidWest Self Guided AI Audio Tours for 7 Days
With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent Mile—or dive deep into 1920s mobster hangouts and hidden Prairie Style masterpieces. Ask about literally anything that catches your eye—from a Gilded Age historic district to a secret jazz club or a towering steel-and-glass skyscraper. The Windy City's deepest secrets are entirely yours to uncover.
Point & Discover: Snap a photo of any monument or museum masterpiece to instantly receive a captivating and accurate story. It’s like having a historian in your pocket!
Ultimate Freedom: Navigate seamlessly with interactive map-based audio tours. Your schedule, your pace, your rules.
Choose Your Vibe: Select a narrator persona that matches your style—from a deep-diving scholar to a fun companion for the kids.
Get Started: 7 Days of Premium Access available instantly for iPhone and Android.
Duration: 7 days
- Free cancellation
![Downtown Chicago City Tour In a Lamborghini[60 Minute Experience]](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-400x400/17/05/8d/da.jpg)
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.
Duration: 45 min – 1 hour
- Private tour
Private Chicago City Minibus Tour
Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town), Millennium Park (The Bean), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its beautiful attractions. Your private tour ensures a more personal experience. If you would like to take the tour at a time other than what is offered, please note in special requests field when booking. The best way to tour at this time! Sanitized vehicles with just your group.
Duration: 2 hours
- Free cancellation
- Private tour
Historic Pullman Private Half-Day Walking Tour
Step into Chicago’s past and explore the story of America’s first model industrial town on this guided walking tour through the Pullman Historic District. Once the heart of George Pullman’s luxury railcar empire, this neighborhood is now a National Monument that beautifully preserves its 19th-century charm and revolutionary history. Wander past rows of red-brick homes, elegant civic buildings, and historic landmarks as your local guide shares the fascinating rise and fall of the Pullman Company—and how a workers’ strike here forever changed labor rights across the country.
- Explore a National Monument – Walk through one of the best-preserved 19th-century industrial communities in the United States.
- Visit historic landmarks – See the Pullman Administration Building, Hotel Florence, Greenstone Church, and the Pullman Historic Foundation Visitor Center.
- Discover labor movement history – Learn how the famous 1894 Pullman Strike shaped the future of workers’ rights in America.
Duration: 4 hours
- Likely to sell out
- Free cancellation
- Private tour