Hear the history behind some of Chicago’s most impressive landmarks on one of these free guided tours.
The Chicago Cultural Center
InstaGreeter Tour Stop at The Chicago Cultural Center. Courtesy of Choose Chicago.

InstaGreeter If you ever longed for a Chicagoan friend to play tour guide on your visit, the InstaGreeter tours might be perfect for you. "It's like you're taking out a friend," says Janice Rosenberg, one of 200 guides volunteering with the city-run program. These tours are short (just about an hour), informal (each guide has their own favorite stops) and packed with local insights. Janice's tour starts under the world's largest Tiffany stained-glass dome (at the Chicago Cultural Center), then it's on to Macy's on State Street, the Picasso at Daley Plaza and the opulent Oriental Theater.

Between landmarks, guides share stories about historical events: the city's early days as Fort Dearborn, the Chicago Fire of 1871 and the 1893 World's Columbian Exposition (aka the Chicago World's Fair). "That's how Chicago became the Second City," Janice says. "The World's Columbian Exposition showed that Chicago had come back from the fire."

Tours leave from the Chicago Cultural Center on the half hour, Friday to Sunday. No reservations required; head to the Chicago Cultural Center and ask for an InstaGreeter tour. chicagogreeter.com/instagreeter

The Chicago Cultural Center
InstaGreeter Tour Stop at The Chicago Cultural Center. Courtesy of Choose Chicago.

Millennium Knickerbocker "Let's step back in a time machine," says concierge Paul Funkhouser, standing in the lobby of the Millennium Knickerbocker Hotel Chicago, a block off the Magnificent Mile. Every Friday at 4 p.m., Paul takes visitors back to the Roaring '20s when this was the Davis Hotel and Al Capone's brother, Ralph, operated a speakeasy and casino on the hotel's 14th floor.

The tour takes guests through a ballroom that had the only lighted dance floor in Chicago and up to the mezzanine level that was home to a 5,000-volume library before it became a USO during World War II. But the highlights are the stories of Prohibition-Era shenanigans. Back then, a secret stairway allowed for quick passage to the 13th floor when law enforcement arrived on the property. "The only thing they ever found up there was a lot of empty coffee cups," Paul says. (312) 751-8100; millenniumhotels.com

Harold Washington Library Center At 10 stories tall and more than 750,000 square feet, the Harold Washington Library Center takes up a full city block and even has its own train stop. So it should come as no surprise that the monthly art tour lasts a full two hours. This is, after all, one of the largest libraries in the United States.

Retired art librarian Anji Holtzman leads small group tours through the $1 million collection of paintings, photographs, sculptures, murals, Civil War-Era furnishings and cannon. Anji shares interesting tidbits about the history of the library, which was named for Chicago's first African-American mayor. The tour concludes in the Special Collections division next to a bookcase filled with gilded tomes that Queen Victoria sent in 1871 as a gift to the city.

Harold Washington Library Center
Courtesy of Harold Washington Library Center

The art tour is offered once a month, usually on the second Tuesday; call to reserve a spot. (312) 747-4800; chipublib.org