Chicago Architecture Cruises, Skydeck Tickets and Walks

The Architecture River Cruise

Chicago's river cruise is the most booked activity in the Midwest, and it deserves it: ninety minutes on the water with a guide explaining the skyscrapers that invented the form. The guided version from the Riverwalk is the most reviewed, the skip-the-ticket-line cruise is the alternative with similar ratings, and the night river and lake cruise swaps the history for the lit-up skyline.

Skydeck and the Views

The Willis Tower Skydeck puts you on a glass ledge 1,353 feet up; the ticket is timed and the line moves fastest before 10am. 360 Chicago on the north side has the Sip and View ticket, a drink with the lake and skyline below. Flyover is the flying theatre at Navy Pier, thirty minutes of aerial footage with motion seats.

Walking Tours Off the Lakefront

The Gangsters and Ghosts walk is the most popular tour on foot, covering the Capone era and the haunted corners of the Loop. The Secret Interiors architecture walk goes inside the lobbies the cruise can only point at, and the Pedway tour explores the underground walkway system most visitors never find.

Seasons on the River

Cruises run from spring to late fall; the river freezes and the boats stop in winter. Summer weekends sell out, so book a morning slot a few days ahead. Most tours offer free cancellation up to 24 hours before.