From Land to Sea: The Windy City's Best Building Tours

Learn more about Chicago's unique and inventive architecture


Back in 1871, the Great Chicago Fire destroyed large sections of downtown, so many of the city's buildings are remarkable not for their history, but for their originality. Chicago is also unique in that some of its best views don’t come from within the city itself but from boat tours along its shoreline. Check out these outstanding Chicago architecture tours to see the city in a new way.

Historic Skyscrapers

Chicago is the birthplace of the skyscraper. It was here that skyscraper engineering and design really took off in the late 19th century in the wake of the Great Fire. Hosted by the Chicago Architecture Foundation, the Historic Skyscrapers tour explores the stories behind some of Chicago's most innovative and iconic skyscrapers, including the The Rookery and the Chicago Board of Trade Building. Tours depart daily from the CAF Shop and Tour Center.

Architectural Cocktail Cruise

Scofflaw offers cocktails to suit any palette and budget, but this Logan Square gem is, at its heart, a gin joint. You're not likely to find a better selection of this often overlooked spirit at any other bar in Chicago. Scofflaw's brick and wood interior gives it a cozy Victorian atmosphere, and if you start to feel a bit hungry, they serve up some tasty small plates that are surprisingly filling.

Must-See Chicago

The Must-See Chicago tour is just the ticket when you want to take in as many significant Chicago landmarks as possible in 90 minutes. It includes sites like the Willis Tower, Wrigley Building and the Art Institute of Chicago, as well as in-depth commentary from knowledgeable Chicago Architecture Foundation guides. Must-See Chicago Tours are on Saturday, Sunday and Monday. They depart from the CAF Shop and Tour Center.

Craft Beers and Community Cheers

Let's not beat around the bush—if you're looking for a dive bar, this is your place. You could call Richard's Bar an old man's bar, and there's not a thing in the world wrong with that. The atmosphere is dingy, the beer is cheap, the jukebox is loaded with Rat Pack classics and the bartenders do not suffer fools. The clientele ranges from local old-timers to college students and out-of-towners looking for a home away from home.

Hop on Hop Off Chicago Tour

Some Chicago architecture tours are best explored at your own pace, and the Hop On Hop Off Chicago Tour allows you to do just that. The brainchild of the Chicago Trolley and Double Decker Company, this 48-hour tour invites you to climb aboard one of the company's trolleys or buses at your leisure. Your tour guide will fill you in on the history of all the downtown highlights while you're on board.

Get on or off at any stop along the tour route. Trolleys and double-decker buses typically make the rounds at each stop every 30 minutes or so. Many stops are located near historically and architecturally significant sites like the John Hancock Center and the Chicago Water Tower.


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