Best of Chicago Walking Tour + River Cruise

What you’ll do:

Explore the heart of Chicago on a dynamic, four-hour adventure combining city walking, landmark visits, and a relaxing architectural cruise. Kick off your tour at Willis Tower’s Skydeck with 360-degree views spanning four states, then stroll past iconic buildings like the Rookery, Palmer House, and Sullivan Center as your guide shares the stories behind their facades.

Stop for an iconic selfie at “The Bean” in Millennium Park before heading toward the lively Chicago Riverwalk and crossing the historic DuSable Bridge. End your tour with a narrated Shoreline Architecture Cruise, where you’ll learn all about the city's famed skyline from the best seat in the house—on the water.

Why we love it for your party:

• Views from 103 floors up make for epic party pics (You’ll literally be standing above the city with the skyline stretching for miles)

• Iconic architecture + fun facts = smart sightseeing (You’ll see historic buildings and actually know what you’re looking at)

• Selfies at the Bean are basically a rite of passage (Capture your group’s best angle with Chicago’s most famous sculpture)

• River cruise = chill time with a view (Relax, chat, and take in 40+ landmarks from a breezy boat ride)

• It’s an all-in-one highlight reel (You’ll hit every must-see spot without having to plan a thing)

About this experience partner:

See Sight Tours brings you closer to the cities you love with immersive small-group experiences led by passionate local guides. Their Chicago day tour blends fascinating stories, architectural wonders, and riverfront relaxation into one seamless journey through the Windy City.

With stress-free logistics and expertly curated stops, See Sight Tours makes it easy for your party to explore, learn, and make unforgettable memories—all in a single, standout day.