Green Mill Jazz Club
4802 N. Broadway Ave.
Red line to Lawrence
Green Mill has that perfect mix of history and modern culture so important to maintain in an evolving city. Opened in 1907 and run by one of Al Capone’s henchmen (“Machine Gun” Jack McGurn) in the 20s, the Green Mill has been hosting live swing and jazz bands for the better part of the 20th century. In addition to the live music, the Green Mill also hosts the world-famous Uptown Poetry Slam on Mondays, which some scholars regard as the first ever organized slam poetry competition, founded in 1986. Just be sure to bring your ID — even for the concerts or poetry shows, the Green Mill is strictly 21+.
Nelson Algren's House
1958 W. Evergreen Ave.
Blue Line to Damen-O'Hare
Winner of the first ever National Book Award for his novel The Man With The Golden Arm, Nelson Algren remains one of Chicago’s (and America’s) forgotten treasures. Enjoying a moderate renaissance in academia — led in part by Northwestern’s own senior lecturer Bill Savage — Algren and his pals Saul Bellow, Mike Royko and Studs Terkel helped reshape the Chicago literary scene in the 60s and 70s. Though he lived in Wicker Park before it was cool, Algren’s modest house (specifically, the third floor apartment) has since become a city icon and landmark. Afterward, check out the Violet Hour on Damen (if you can find it — there’s no sign above the door, and also no “door”) for one of their famous cocktails.
Fort Dearborn
Intersection of Michigan and Wacker
Red Line to State/Lake
Way back before Chicago was officially incorporated as a town in 1833, there was Fort Dearborn. Built in 1803 to guard the western territories, the fort was razed by a Potawatomi Indian tribe during the War of 1812. The site of the original fort (about where Michigan and Wacker intersect, just south of the river) now houses some incredible statues and memorials of the battle by American sculptors Henry Hering and James Earle Fraser. After paying your respects, hop across the river to the famous Billy Goat Tavern (430 N. Michigan Ave.) and see if you can find one of Mike Royko’s columns about the fort tacked on one of the walls.
The Silver Palm
768 N. Milwaukee Ave.
Blue Line to Chicago-Blue
Located in River West by the Kennedy Expressway, The Silver Palm is pretty much your run-of-the-mill restaurant and bar, except for one small detail: the restaurant’s located inside a refurbished 1947 dining car. The dining car, named after an Amtrak train that used to run on the Atlantic Coast Line from Washington, D.C. to Miami, opened as a restaurant in 2003. The menu consists largely of American comfort food and an extensive bourbon and scotch list, as if the car were still making the 30-hour trip. The restaurant shares a sidewalk (and a friendly rapport) with next-door bar The Matchbox, and if you’re looking for some culture after your lunch, Intuit: The Center for Intuitive and Outsider Art is just a block away.
Robie House
5757 S. Woodlawn Ave.
Green Line to Garfield-Green
Guys, I’m gonna level with you. I like to play up the Northwestern/University of Chicago rivalry as much as the next guy. So for me to tell you to make the trek all the way down to our city rival’s campus, you need to just trust me. Located in Hyde Park, Robie House is perhaps Frank Lloyd Wright’s most famous design, the prime example of his prairie style of architecture and a designated historical landmark and a member of the National Register of Historic Places. It’s breathtaking. Just be sure to wear some purple down on their turf.
Northerly Island
Museum Campus
Red Line to Roosevelt
Say what you will about the old mayor, Richard M. Daley, but he spent a lot of time and money beautifying the city. Northerly Island used to be the site of Meigs Field, a single strip airport south of the planetarium. In 2003, Daley famously snuck out in the middle of the night and destroyed the airstrip, citing “homeland security” purposes, and subsequently unveiled city plans that coincidentally converted the island into green park space and incorporated it into the museum campus. Located just south of Adler Planetarium (which was beautifully renovated for the 2011 season), Northerly Island boasts some of the best parkland and beaches in the city. The museum campus is best known for the Field Museum and the Shedd Aquarium, but Adler and the rest of the island are worth checking out as well. A peninsula jutting out into the lake, the shore just north of the Planetarium provides my personal favorite view of the city skyline and are a great photo-op.