This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where architectural landmarks are illuminated with festive displays. How do Europea... More

Chicago can sometimes feel inaccessible to visitors, but a private walking tour with a local guide takes the mystery out of the city. This personalized tour focuses on the exteriors of iconic monuments, including museums, while yo... More

Much of the historical information shared on this tour is unknown to most attendees. This tour also shows everything from the gritty to the pretty, from the mundane to the magnificent.... More

Start your immersive walking tour at a Chicago icon: the Centennial Fountain at River Esplanade Park. From here, your guide will take you on a culinary and cultural adventure. Our first stop is the famous Billy Goat Tavern, wher... More

Sipping Our Way Through History Visit some of the best cocktail bars and tavern that line the streets of Galena. Galena once boasted over 60 bars and taverns, come explore why Galena is often referred to as the town that time forg... More

On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hancock Tower. Your guide is a local who has plenty of tales about Chicag... More

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding a bike. Dive into the atmosphere of the city’s movement and c... More

There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through the Chicago Loop, Millennium Park, & the Magnificent Mile with an internatio... More

Take a spin through the Windy City on a bike tour and discover the most remarkable and world-famous sights. Hit the streets like a local with your guide, dive into the bustling life of the business districts, be welcomed by the so... More

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying architectural styles and see how older structures connect to new s... More

Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a recent transplant to Chicag... More

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists. Along the way, we'll discuss some of the people, and people groups, ... More

Taste four different styles of pizza in about three hours. Learn about Chicago's 10 pizza styles, and discover why there's more to The Windy City than just deep-dish. Go back in some of the kitchens to see how pizzas are made, an... More

Make the best of your visit to Chicago and explore the interiors of the emblematic Loop of Chicago downtown with a private licensed guide. You will enjoy a private tour and discover the hidden architectural treasures of Chicago wi... More

Capture your Chicago adventure with a professional photoshoot at the city’s most famous landmarks. Perfect for solo travelers, couples, or friends — no posing experience needed! We’ll visit: The Bean, Chicago Theatre, River... More

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get a unique chance to combine touring by foot a... More

Learn about the life and work of Louis Comfort Tiffany as we visit some of Chicago’s most magnificent art-glass and mosaic installations, each designed and crafted by the Tiffany Glass and Decorating Company. In the late 19th C... More

Enjoy moving at your own pace through Chicago's Millennium Park with an app as your guide. You and your private party can stop or start the app whenever you like; pausing to explore further on your own. Take in the sights of the p... More

A dating app. A stranger with arctic blue eyes. A meeting in Lincoln Park on Halloween. This self-guided ghost escape game drops you into Chicago's most haunted park, where thousands of bodies still lie beneath the grass. Solve 1... 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