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Top 10 Chicago Institutions
1. Green Mill
Music, art and gangsters. Green Mill boasts a rich and interesting history that’s Napoleonic in scope. Slinging drinks under its current name since 1910, this joint was a popular hangout for Al Capone and also owned by his right-hand man “Machine Gun” Jack McGurn. It still features a network of underground passages that came in handy during police raids in the ‘30s. Appearing in several films, including Michael Mann’s Thief and The Joker is Wildstarring Frank Sinatra it has undoubtedly bolstered its reputation — but it’s the nightly performances that keep the regulars coming back. Weekly poetry slams pack in an artsy crowd, while late-night jazz sessions that carry on until 4 a.m. entertain patrons sipping on classic cocktails and chatting it up in a respectfully restrained tone. Simply put, the Green Mill is Chicago in a nutshell.
2. Palmer House Hilton
Showcasing the grandeur and sophistication of Chicago’sarchitecture, as well as the opulence of the social hierarchy’s upper crust, the Palmer House Hilton is an enduring symbol of the city’s emergence as a world-class destination. Built in 1871, the grandiose hotel burned down 13 days later in the Great Chicago Fire. With almost fanatical determination, the owner immediately set to rebuilding the structure with a head-spinning amount of loaned money. The result is Chicago’s second largest hotel and a resplendent lobby that’s one of the finest you’ll ever see.
3. Schaller’s Pump
Opened in 1881, this south-side White Sox fan haven has remained one of the most time-tested joints in the entire city. Not that first-time visitors would notice when perusing the unassuming confines or mingling with the shot-and-beer swilling patrons. Owning Chicago’s oldest liquor license, Schaller’s Pump also holds the distinction of being the oldest continually running bar in the city. Thanks to the 11th ward democratic headquarters nestled right across the street, Schaller’s has also been a favorite hangout of Da Mare (“the mayor” in Chicago-speak), as well as his pops, the late Richard J. Daley.
4. The Berghoff
A veritable Chicago landmark and fixture of the bustling Loop since 1898, The Berghoff provides locals with an opportunity to sample tantalizing German fare without having to bus it up north to Milwaukee. After prohibition was repealed in 1933, this joint got the city’s first renewed liquor license. Though it shut down temporarily in 2006, things are back in full swing, allowing schnitzel-yearning patrons to fill up on hearty grub and palatable pours of a wide range of beers
5. Manny’s Deli
Since moving to its current South Loop locale in 1964, Manny’s has managed to cultivate its rep on nearly hysterical praise from the pastrami-yearning regulars. While Manny’s specializes in serving up scrumptious slices of sandwich meat aside homey Jewish fare, such as kreplach and potato pancakes, it’s really the old-school vibe of this quintessential deli that makes it such a standout spot. Blue-collar workers, businessmen and politicos stop in daily and fill up their cafeteria trays with mountainous sandwiches. Swing by and pick up the President’s Special, a favorite of the one and only Barack Obama
6. The Pump Room
Nestled within Gold Coast’s regal Ambassador East Hotel, The Pump Room boasts more history than a dusty set of hardcover almanacs. Welcoming visiting celebrities and hotshots since 1938, this swank eatery fills up its luxe confines with hungry patrons looking to experience a bit of the spot’s glamorous past. The coveted “booth one” has hosted the likes of Frank Sinatra, Paul Newman and David Bowie. Phil Collins named an album after an incident that took place here (No Jacket Required), and The Pump Room has also been referenced in "Chicago (That Toddlin’ Town)” and “My Kind of Town (Chicago is).” Don’t be surprised if a rap song shout-out is next on the list.
7. Gene & Georgetti
Throw a stone in any direction while strolling through downtown and chances are you’ll hit a decent steakhouse. With so many options for sizzling slabs of scrumptious meat available, Gene & Georgetti has differentiated itself from the pack by simply outlasting the competition. The oldest steakhouse in town, G&G has been whipping up delectable Italian dishes and steaks since 1941. Nothing much has changed since then, with cigar-toting gentlemen being replaced by Blackberry-toting gentlemen. It’s a can’t-miss eatery, where memorable meals are served up in a spot that’s seemingly frozen in time.
8. Kingston Mines
Slowly but surely, the blues is beginning to fade away. Legends such as John Lee Hooker and Junior Kimbrough pass away while kids learn how to freestyle or DJ instead of huff and puff away on a harp. As the city’s oldest and largest blues joint, Kingston Mines has been keeping the sweet music alive on the north side since 1968. Popular with tourists and locals alike, the spot offers two stages, music seven nights a week, down-home soul food, and discounts for local DePaul students — ensuring a rowdy crowd on the weekends. Something tells us it’ll be a while before Kingston Mines locks up for good.
9. Boom Boom Room At Green Dolphin Street
Getting crowds to come back every week for a nightly bash is oftentimes a headache-inducing struggle for many clubs. That’s why Green Dolphin Street’s 18-year run of hosting its Monday night Boom Boom Room party is so intriguingly mind-blowing. Since 1992, a melange of LGBT clubgoers and backward-hat toting bros have been getting down here to Chicago-bred house music with infectious alacrity while simultaneously wreaking havoc on their workweek productivity.
10. Superdawg
If there’s one thing that Chicagoans can agree on, it’s that ketchup should never, ever come in contact with a hot dog. Superdawg definitely subscribes to that adage, and even takes its refreshing traditionalism one step further. Since opening in 1948, this northwest-side drive-in hot doggery has never altered its culinary methods or recipes. The formula works, and has brought the seminal hot dog stand massive media coverage over the years from a bevy of travel shows and publications. Stop by to munch on one of the city’s classic hot dogs and snap some photos in front of the hot dog versions of Tarzan and Jane perched atop the roof.
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