easy
2–3 hours
Participants should be comfortable walking continuously for a few hours over flat urban terrain.
Explore Chicago’s architectural legacy and vibrant culture on this expert-led urban tour. Walk through history and modernity in one of America’s most iconic cities.
Starting at $44 | 2.5 Hours | Experience one of the most architecturally striking cities in the U.S!
Duration: 2.5 hours Price Adult (Ages 12+): $49 Child (Ages 6-12): $44 Young Child (Under 6): Free
Chicago has it all – amazing architecture, great food, and iconic sights both old and new. This 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.
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 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 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.
Inclusions: Local, English-speaking guide, various flavors of popcorn tasting, chocolate tasting
Exclusions: Additional food or drinks, souvenirs and personal shopping, tips/gratuities for your guide.
Notes:
This tour involves several hours on foot through city streets and riverwalk paths. Comfortable shoes are a must.
Chicago weather can change quickly; bring layers and a rain jacket if needed.
Staying hydrated is key during urban explorations, especially in summer months.
Daytime rush can affect transit; arriving early helps you start the tour stress-free.
Chicago’s rebirth after the Great Fire of 1871 spurred a building boom that shaped its renowned skyline.
The city's Riverwalk incorporates sustainable design elements promoting native plants and reducing runoff into Lake Michigan.
Support and comfort for extended city walking.
Manage unpredictable spring temperatures and possible rain.
spring specific
Protection during sunny summer days outside.
summer specific
Stay warm and shielded from fall breezes near the lake.
fall specific