An architecture cruise on the Chicago River is the tour most visitors put first, and for good reason: the city's buildings are best seen from the water. The Chicago Architecture Center River Cruise, run with First Lady boats from East Wacker Drive, uses the Center's docents and runs from mid-March to late November. Wendella Boats, family-owned since 1935, sails year-round on climate-controlled vessels, while Shoreline Sightseeing, operating since 1939, adds skyline lake tours, fireworks cruises and a water taxi between downtown docks.
On land, Chicago Food & City Tours runs food walks through the West Loop, Chinatown, Pilsen and Lincoln Park, along with a classic Chicago foods tour and one inspired by The Bear. Bobby's Bike Hike offers guided bike tours and a walking food tour from Lake Shore Drive. Book boat tours ahead for summer weekends, bring a layer for the wind on the water, and check dietary rules before booking food tours.
5 places · Updated October 27, 2026
Our top 3 tours & activities in Chicago
Tour operator
The Chicago Architecture Center's river cruise aboard First Lady boats introduces the city's buildings from the water, with commentary from the Center's docents.
View details — Chicago Architecture Center River CruiseTour operator
Wendella Boats is a family-owned Chicago boat company founded in 1935, running river architecture tours, lake and river cruises and sunset trips all year.
View details — Wendella BoatsTour operator
Shoreline Sightseeing has run boat tours in Chicago since 1939, offering architecture river tours, skyline lake tours, fireworks cruises and a water taxi between downtown docks.
View details — Shoreline SightseeingTour operator
Chicago Food & City Tours runs guided food walks through neighbourhoods such as the West Loop, Chinatown, Pilsen and Lincoln Park, plus a tour of classic Chicago foods.
View details — Chicago Food & City ToursTour operator
Bobby's Bike Hike runs guided bike, walking and food tours from 540 North Lake Shore Drive, including a city bike tour and a bike tour with signature dishes.
View details — Bobby’s Bike Hike