Best of Chicago History & Architecture Walking Tour with Optional Boat Cruise

What you’ll do:

Take in the best of Chicago on foot with this immersive walking tour through the city’s most iconic landmarks, vibrant neighborhoods, and scenic routes. You’ll start at Millennium Park to admire the famous Cloud Gate, then explore the Chicago Pedway’s hidden tunnels before strolling the beautiful Riverwalk.

Continue up the Magnificent Mile, crossing the historic Michigan Avenue Bridge and passing legendary buildings like the Wrigley and Tribune Towers. You’ll also get a chance to taste a savory Chicago treat and check out the Starbucks Reserve Roastery.

Want more? Choose the option to end your experience with a relaxing boat ride on the Shoreline Architecture Cruise for views of over 40 iconic buildings from the water.

Why we love it for your party:

• Snap a pic at “The Bean” in Millennium Park (Because no Chicago photo dump is complete without it)

• Wander the secret tunnels of the Chicago Pedway (Explore a whole underground world hidden beneath the city)

• Take a bite out of the Windy City (Grab a classic Chicago treat while you stroll)

• End with a skyline boat cruise (Opt for our popular tour with the boat cruise included to enjoy city views from the water after a day of exploring)

• It’s got the perfect mix of iconic and unexpected (This walking tour hits the highlights and the hidden gems)

About this experience partner:

See Sight Tours is a leading provider of small-group and private tours, known for creating curated local experiences with top-rated guides, smooth logistics, and insider access. In Chicago, their walking and boat tours offer an up-close look at the city’s famous architecture, deep history, and unique culture—all delivered with engaging storytelling and personal flair.

With See Sight Tours, guests skip the typical tourist routine and experience the heart of the city like a local.

Additional information:

• The walking tour is $49 per person and lasts 2.5 hours, and the walking tour with boat cruise included is $104 per person (the boat cruise adds an extra hour)