Touring Chicago Landmark Attractions

Three separate companies run architecture cruises from three separate docks, and mixing them up means showing up at the wrong bridge. Here is who runs what, and what else is worth booking in advance.

Architecture river cruises: three operators, three docks

The Chicago Architecture Center’s cruise aboard Chicago’s First Lady departs from 112 E. Wacker Dr, at the Riverwalk by the Michigan Avenue Bridge. It runs 90 minutes, narrated by CAC-trained volunteer docents, and covers over 50 landmarks along the Main, South, and North branches, for $57 to $67 depending on time of day. Book the CAC river cruise through architecture.org . Wendella Boats, Chicago’s oldest operator since 1935, docks at 400 N. Michigan Ave by the Wrigley Building and offers 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, and its tour is the one included on Chicago CityPASS. Compare river cruise options on GetYourGuide . Cruises run seasonally, roughly April through November, and stop once the river starts icing over.

Willis Tower Skydeck

At 233 S Wacker Dr, the 103rd-floor Skydeck sits 1,353 feet up and includes The Ledge, four glass balconies that extend 4.3 feet out over Wacker Drive. General admission starts around $32 for adults and $24 for youth, with expedited entry from $55. Hours run 9am to 10pm in warmer months and shorter in winter; check current times at theskydeck.com .

Navy Pier’s general admission is free, and the 3,300-foot pier holds the Centennial Wheel ($19 to $21 adult), Chicago Children’s Museum, and the Chicago Shakespeare Theater. Each winter it hosts Winter WonderFest, an indoor carnival with rides and ice skating that most recently ran December 5, 2025 through January 4, 2026, alongside the newer Summer Skate roller rink. Free fireworks light the pier on Wednesday and Saturday nights between Memorial Day and Labor Day.

Hop-on hop-off buses

Big Bus Tours is the only open-top hop-on hop-off operator left downtown, covering 12 to 14 stops including Millennium Park, the Skydeck, Navy Pier, and Museum Campus on a roughly two-hour loop. A one-day ticket runs $45 to $52 for adults; a two-day ticket runs $58 to $68. See current Big Bus routes and pricing . Chicago Trolley Company closed for good at the end of 2019, so any listing that still mentions vintage street trolleys downtown is out of date.

Museum Campus and Millennium Park

The Field Museum, Shedd Aquarium, and Adler Planetarium sit together on Museum Campus south of Grant Park; each sells its own ticket separately, since no joint box-office pass links them to the Art Institute across town. Nearby, Millennium Park is free and holds Cloud Gate and the Jay Pritzker Pavilion, worth pairing with a river cruise dock a short walk north.

The verdict: pick one river cruise operator based on your dock, not all three, and put the Skydeck or 360 CHICAGO on a clear day rather than booking blind. For a hotel near the Riverwalk docks, search Chicago stays on Booking.com , and pair this with the sightseeing guide for the observation decks in more depth.