Lonely Planet Experiences Private Chicago Tour: Culture & Architecture

Chicago has it all – amazing architecture, great food, and iconic sights both old and new. This private tour takes you to some of the city’s best spots alongside a local guide where you’ll get the inside scoop on what makes Chicago so special. Not only that, we’ll throw in a couple of sweet, local treats to keep you going as we explore on foot and via local transportation.

This tour is priced for a minimum group size of four travellers. A solo traveller may still book this private experience but will be charged the base rate for four travellers

Experience the best travel stories for yourself. Join a local expert and uncover hidden gems on this city adventure hand-picked by the world's leading travel publisher. Lonely Planet Experiences powered by Urban Adventures bring stories to life in the best-loved cities around the globe.

Chicago is known as one of the most architecturally striking and culturally dynamic cities in the United States. Join us on a tour of some of Chicago’s greatest hits: incredible architecture both old and new, delicious local treats, a uniquely Chicago transit ride, stunning river views, and much more! 

We start our private tour under the dazzling marquee of the Chicago Theater (where you might recognize the neon sign from the movie musical Chicago) before heading off into the bustling city. Our first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core. 

We’ll then head towards the Chicago Pedway. This unique feature of Chicago is used by locals and commuters daily to move about the city in a network of underground tunnels — especially necessary during the Midwest winters. We’ll head back above-ground near City Hall, and on most weekdays, be able to head inside to see the classic interior design and architecture. 

Next, we’ll make our way to a spot where we’ll share a sweet treat, and a local tradition: Chicago-style popcorn. Weather permitting, we’ll take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Sears Tower (now known as the Willis Tower). 

From there, we’ll either hop on the ‘L’ train or a water taxi on the Chicago River (depending on the weather and time of year). Either option offers a uniquely local Chicago experience! The ‘L’ train is recognized as a Chicago landmark having been featured in movies and TV shows for decades. You’ll enjoy feeling like a local as you zip past buildings and catch even more awesome views. If your guide takes you on a water taxi, you’ll be seeing the Chicago skyline from a totally different perspective, as well as sharing in the daily commute of local Chicagoans late for work. 

Once you’re back on solid ground, we’ll make our way to another delicious destination. Along the way, you’ll be able to enjoy views of the world-famous Wrigley Building and the incredible Chicago Tribune building, the heart of Chicago’s thriving and historic journalism industry. Your second tasty confection is locally made chocolate from a Chicago staple. 

Finally, we’ll take a stroll through the beautiful lakefront parks along Michigan Avenue. We’ll end up in the picturesque Millennium Park, home to the iconic Bean sculpture. Here (or nearby), your guide will conclude your tour and point you in the right direction toward more amazing sights, great lunch spots, or a drink recommendation inside one of the most amazing spaces in the city. 

This tour is priced for a minimum group size of four travellers. A solo traveller may still book this private experience but will be charged the base rate for four travellers