Best of Chicago: First Elevator Access at Willis Skydeck, Architecture Cruise, & Inside the Loop Tour

Get an insider’s look at Chicago’s iconic architecture—from legendary skyscrapers to lesser-known gems.

Home to the city's most impressive architecture and its most storied buildings, the Loop has been the beating heart of Chicago for over a century. In the city that gave the world its first skyscraper, there truly is no better place to start your visit than at the feet (and at the top!) of these giants—and no better company than our experienced, expert local tour guides.

We’ll meet at the Monadnock Building and head straight to nearby Willis Tower, where we’ll take the day’s first elevator up to the Skydeck! From this jaw-dropping vantage point atop the third-tallest building in the US, our expert guide will show you all of Chicago—and beyond—laid out before you. It’s the perfect place to get the lay of the land and take a bird’s-eye view of the rest of the sights you’ll be seeing today.

From there, you’ll stroll through the financial district and revel in Chicago’s imposing Art Deco architecture, which is designed to make you look up. Towering atop the magnificent Board of Trade Building, you’ll see the three-story-high statue of Ceres, the Greek goddess of corn and wheat, looming over the streets.     

Next, you’ll enter a breathtaking lobby designed by a young Frank Lloyd Wright and be astounded by the secret glass mosaics adorning interiors throughout Chicago that only an in-the-know local would be able to point out. 

As you continue your exploration of the Loop, you’ll hear the stories of the colorful characters that brought this city to world prominence. Marvel at the intricate golden peacock doors at the Palmer House—birthplace of the brownie—and stand in awe of the largest Tiffany glass dome in the world. 

Then it's on to Millennium Park and the world-famous Cloud Gate sculpture. After posing in front of the Bean, we’ll head up Michigan Avenue to check out more architectural quirks (wait, does that building look like a champagne bottle?).   

Finally, we’ll head to Chicago’s iconic Riverwalk. To wrap up your morning of exploring, sit back and relax on a 90-minute architecture cruise along the Chicago River and Lake Michigan. If you’re hungry from all that walking, don’t worry—there are snacks and refreshments available for purchase on board!

After nearly six fascinating hours, you’ll have experienced Chicago’s incredible architecture from the sky, streets, and water, and know how each structure fits into the city’s story.

Sites Visited
Monadnock Building, Chicago Board of Trade with Ceres Statue, Skydeck at the Willis Tower, Federal Reserve, Rookery Building (interior), Marquette Building (interior), Inland Steel, Palmer House (interior), Carson Pirie Scott Building, Marshall Field Building (interior), Chicago Cultural Center (interior), Millennium Park, Cloud Gate / The Bean, Michigan Ave., Riverwalk, DuSable Bridge, Chicago River & Lake Michigan