Historic Site in Lincoln Park & Old Town

Biograph Theater

In 1934 the ‘lady in red’ betrayed gangster John Dillinger at this theater, which used to show movies. FBI agents shot him in the alley beside the building.
Historic Site in The Loop

Route 66 Sign

Attention Route 66 buffs: the Mother Road’s starting point is here. Look for the sign that marks the spot on Adams St’s south side as you head west toward Wabash Ave.
Historic Building in South Loop & Near South Side

Willie Dixon's Blues Heaven

From 1957 to 1967, this humble building was Chess Records, the seminal electric blues label. It's now named for the bassist who wrote most of Chess' hits. Staff give hour-long tours of the premises. It's pretty rams…
Historic Site in Hyde Park & South Side

Pullman National Monument

Pullman got its national park certification in 2015. Its significance? It offers a rare look at a capitalist's fallen utopia. The community's design and architecture make for a fascinating walkabout. The Historic Pu…
House in Hyde Park & South Side

Obama's House

Hefty security means you can’t get close to Barack Obama’s house, but you can stand across the street on Hyde Park Blvd and try to glimpse over the barricades at the redbrick Georgian-style manor. He and his family …
Historic Site in Wicker Park, Bucktown & Ukrainian Village

Nelson Algren's House

You can’t go inside, but on the 3rd floor of this apartment building writer Nelson Algren created some of his greatest works about life in the once down-and-out neighborhood. A plaque marks the spot. Algren won the …
Historic Building in Hyde Park & South Side

Meyers Ace Hardware Store

Jazz aficionados often seek out the unassuming Meyers Ace Hardware Store. Why? Because in the 1920s and ’30s the building was the Sunset Cafe, where all the greats gigged. Imagine Louis Armstrong blowing his trumpet…
Historic Site in Hyde Park & South Side

Union Stockyards Gate

The castle-like gate was once the main entrance to the vast stockyards where millions of cows and hogs met their ends each year. During the 1893 World’s Expo the stockyards were a popular tourist draw, with nearly 1…
Historic Site in Lincoln Park & Old Town

St Valentine's Day Massacre Site

At this infamous spot on February 14, 1929, Al Capone's henchmen, dressed as cops, lined up seven members of Bugs Moran's gang against the garage wall that used to stand here and sprayed them with bullets. After tha…
House in Hyde Park & South Side

Muddy Waters’ House

At Muddy Waters’ house, impromptu jam sessions with pals like Howlin’ Wolf and Chuck Berry erupted in the front yard. Waters, of course, was Chicago’s main bluesman, so everyone who was anyone came to pay homage. Wa…