Exclusive Private Chicago City Tour: River Cruise, Skydeck, Bean & Hotel Transport

What you’ll do:

Experience the very best of the Windy City on a private, fully guided tour just for your group. With skip-the-line entry to top attractions and a knowledgeable local guide by your side, you’ll start at the Skydeck Chicago for jaw-dropping views from the 103rd floor (and a heart-pounding walk on The Ledge).

Then head to Adler Planetarium Pier for a postcard-perfect skyline view before hopping aboard a narrated Shoreline Architecture Cruise to learn about Chicago’s world-renowned buildings from the water. Wrap up the day with iconic photo ops at Buckingham Fountain and The Bean, and enjoy hassle-free pick-up and drop-off right from your downtown hotel.

Why we love it for your party:

• It’s your own private VIP experience (Just your group, a fun guide, and zero strangers tagging along)

• The Ledge is pure adrenaline (Stand on a glass box 1,353 feet above the city for a thrill you’ll all talk about later)

• The skyline from Adler Pier is unmatched (Snap some of the best group shots of your entire trip)

• Cruising the river is both relaxing and Insta-worthy (Great architecture, chill vibes, and even better views)

• You hit every major highlight without the crowds (From The Bean to Buckingham Fountain, it’s all streamlined for you)

About this experience partner:

See Sight Tours is known for its intimate, small-group experiences led by passionate local guides who deliver unforgettable city adventures. Their private Chicago tour offers the perfect blend of iconic sights, architectural wonders, and personalized insight—all with VIP perks like hotel pick-up, skip-the-line access, and a dedicated guide.

Whether you're new to the Windy City or looking for a fresh way to explore it, this private tour makes sightseeing seamless, fun, and totally unforgettable.