Let’s take photos at one of Chicago’s most famous spots - the bright red CHICAGO sign at the Chicago Theatre! During this 30-40 minute photo walk, I’ll help you pose and feel comfortable while taking high-quality photos usin... More

This is not a bus tour, 90% of our tours are 11 people or less, as we specialize in small, personalized group tours. This gives us the space and time to take pictures and have great conversation! The personal, small tour approach ... More

This is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into the streets to showcase and highlight the vibrant street art scene, which many people overlook on a daily basi... More

On A Boat Sailing offers an all-inclusive, private VIP sailing experience departing from the brand-new Navy Pier Marina in Downtown Chicago. If you appreciate attention to detail, hospitality, and sophisticated service, this is th... More

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have the experience of a lifetime!... More

Explore the wonders of the Field Museum with general admission that covers all open general exhibitions, including the Griffin Halls of Evolving Planet & SUE the t. Rex. Enjoy unique access to the Grainger Hall of Gems and the eng... More

One of a kind experience you can only find in Chicago. Motorized paddle boards take the stress out of paddling. LED-lights make the boards illuminate the water providing a personal light show.... More

Experience the story of Chicago through its skyline on a walking tour that stretches from the city’s 19th-century roots to its most striking modern towers. From Beaux-Arts to modernist to Art Deco, this architecture tour has it ... More

Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking parks, the famous Cloud Gate (The Bean), world-class museums, and reno... More

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing travellers around the world, our small team ... More

The Offbeat Street Art Tour is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into the streets to showcase and highlight the vibrant street art scene which many people ov... More

Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza, Garrett’s Popcorn, and Do-Rite Donuts while exploring top city la... More

The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights around the local waterways including the Navy Pier, Soldier Field, ... More

Chauffeurs are knowledgeable and professional, always on time, and well dressed. Chauffeurs are highly trained that safety is our number one priority. We also make bookings hassle free with our QR code available at your fingertips... More

Flytographer Private Vacation Photo Shoot Connect with a local hand-picked professional photographer in Chicago and capture your most memorable moments during this private photo shoot. Get insider tips on the best things to do in... More

Step into the birthplace of the modern skyscraper on this immersive walking tour through Chicago’s historic Loop. Discover the stories, innovations, and hidden details behind the buildings that shaped the modern city. What makes... More

Experience the magic of Chicago at dusk on a 90-minute live guided panoramic adventure that captures the city in its most captivating light. Watch the entire skyline come to life, from Magnificent Mile to Museum Campus and beyond.... More

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Take a detour off the beaten path, and explore the flavors of Chicago’s delicious West Side with Bobbys's Bike Hike & Food Tours, America's longest running city bike tour company, who recently ranked as Top 20 Food Tours in the ... More