Premium guided tours and luxury sightseeing adventures through the Windy City's most iconic landmarks and hidden gems
Book Your Tour TodayYour premier partner for unforgettable Chicago travel experiences
Founded in 2015, Signature Sightseeing has been Chicago's leading premium tour operator, specializing in luxury guided experiences that showcase the city's rich history, stunning architecture, and vibrant culture. Our expert local guides possess intimate knowledge of Chicago's neighborhoods, from the iconic Loop district to the charming lakefront communities.
We pride ourselves on delivering personalized, small-group tours that go beyond typical tourist attractions. Our carefully curated itineraries include exclusive access to hidden gems, architectural marvels, and cultural hotspots that most visitors never discover. Whether you're interested in Chicago's famous deep-dish pizza scene, world-class museums, or breathtaking skyline views, we create memorable experiences tailored to your interests.
With over 50,000 satisfied customers and partnerships with Chicago's top attractions, restaurants, and cultural institutions, Signature Sightseeing continues to set the standard for luxury travel experiences in the Midwest. Our commitment to excellence has earned us recognition as Chicago's #1 boutique tour company.
Carefully crafted experiences designed to showcase Chicago's best
Explore Chicago's world-renowned architecture with expert guides who bring the city's skyline to life. From Frank Lloyd Wright masterpieces to modern skyscrapers.
Taste your way through Chicago's legendary food scene, including authentic deep-dish pizza, Italian beef, and gourmet dining experiences.
Immerse yourself in Chicago's rich cultural heritage with visits to world-class museums, theaters, and neighborhood cultural centers.
Discover Chicago's beautiful lakefront, Navy Pier, and stunning beaches along Lake Michigan with our scenic waterfront excursions.
Uncover Chicago's fascinating history from the Great Fire of 1871 to the rise of the modern metropolis we see today.
Personalized luxury experiences tailored to your interests, schedule, and group size with dedicated private guides and transportation.
Experience the difference that premium service makes
Professional guides with extensive Chicago knowledge and storytelling expertise
Comfortable, climate-controlled vehicles with panoramic windows for optimal viewing
Intimate groups of maximum 12 people for personalized attention and flexibility
Flexible tour options that can be tailored to your interests and preferences
Special access to attractions and experiences not available to regular tourists
Award-winning customer service with 24/7 support and satisfaction guarantee
Real experiences from our satisfied customers
Absolutely incredible experience! Our guide Maria was knowledgeable and passionate about Chicago's history. The architecture tour exceeded all our expectations, and we saw parts of the city we never would have discovered on our own.
The culinary tour was a foodie's dream come true! We tried authentic deep-dish pizza, visited local markets, and discovered amazing restaurants we never would have found. Professional service and great value for money.
Our private family tour was perfectly customized for our group. The kids loved the interactive elements, and we adults appreciated the in-depth historical insights. Signature Sightseeing made our Chicago vacation unforgettable!
Ready to explore Chicago? Get in touch with our team
125 Michigan Avenue
Chicago, IL 60601, USA
Monday - Sunday
8:00 AM - 8:00 PM