Chicago's Best Attraction Tours and Passes

Three companies run architecture cruises from three different docks around downtown Chicago, which trips up plenty of visitors who show up at the wrong bridge. Here is who runs what.

Architecture river cruises

The Chicago Architecture Center’s cruise aboard Chicago’s First Lady leaves from 112 E. Wacker Dr at the Riverwalk, a 90-minute trip narrated by CAC-trained volunteer docents past more than 50 landmarks, for $57 to $67. Book the CAC cruise through architecture.org . Wendella Boats, running since 1935, docks at 400 N. Michigan Ave by the Wrigley Building, with a 45-minute river tour from $28 or a 90-minute river-and-lake cruise through the Chicago Harbor Lock from $45. Shoreline Sightseeing runs shorter 60 to 75 minute tours from Navy Pier and the Michigan Ave Bridge for $46 to $50, the version bundled into Chicago CityPASS. Compare river cruise times on GetYourGuide . All three run seasonally, roughly April through November.

Skydeck Chicago at Willis Tower

At 233 S Wacker Dr, the Skydeck occupies the 103rd floor at 1,353 feet, with The Ledge, glass balconies extending 4.3 feet out over Wacker Drive. General admission starts around $32 for adults, with expedited entry from $55. Hours run longer in summer than winter; check current times at theskydeck.com .

Museum Campus

The Field Museum, Shedd Aquarium and Adler Planetarium sit together south of Grant Park. Each sells its own separate ticket; there is no joint box-office pass linking any of them to the Art Institute of Chicago across town, so budget each admission individually.

Navy Pier is free to enter, with the Centennial Wheel, Chicago Children’s Museum, and Chicago Shakespeare Theater along its length. Each winter it runs Winter WonderFest, an indoor carnival with rides and ice skating, most recently December 5, 2025 through January 4, 2026, alongside the newer Summer Skate roller rink.

Hop-on hop-off buses

Big Bus Tours is the sole open-top hop-on hop-off operator left downtown, running 12 to 14 stops including Millennium Park, the Skydeck, Navy Pier, and Museum Campus on about a two-hour loop. A one-day ticket runs $45 to $52, a two-day ticket $58 to $68. See current Big Bus routes . Chicago Trolley Company shut down for good at the end of 2019, so skip any listing still promoting vintage street trolleys downtown.

Planning your tours

Book popular attractions online ahead of time, since several sell out same-day slots in peak season. Wear comfortable shoes; a river cruise plus a Loop museum easily adds up to several miles of walking between docks and entrances.

The verdict: pick your river cruise operator by which dock is closest to your hotel rather than trying to compare all three, and save the Skydeck for a clear-sky day rather than booking it blind. For a room within walking distance of the Riverwalk docks, check rates on Booking.com , and see the sightseeing guide for the observation decks in more depth.