From Barack to the Rat Pack, Chicago has always been the promised land of thick steaks, great jazz, good drinks and handsome haberdasheries. Here’s a picture of the city, from its classics to its cutting edge.

Manny's

The walls of Manny’s delicatessen are lined with newspaper clippings and photos detailing its 70-year history of making Chicagoans globular. Start with kreplach soup, then fill your plate once, twice, four times with corned beef and pastrami on rye, kishke and giant, mouth-watering potato knishes (with meat in the middle!). The guys behind the counter won’t even blink at your excess. “We do this all day,” one told us, nonchalantly shifting the toothpick in his mouth in a way that proves that yes, they do indeed. 

David Burke's Primehouse

The low lighting and leathery browns of the dining room may be easy on the eyes, but the magic of Primehouse happens in the dry-aging room, where shelf upon shelf of chuck, rib-eye and sirloin are stacked up against a wall lined with marbled blocks of Himalayan pink salt tiles. Starters of Wagyu beef sashimi and lobster spring rolls set the scene for pop-over biscuits to go with scallops as thick as steaks and steaks as tender as scallops, and when by meal’s end we dug our teeth deep into our luscious steak bone, one of the staff leaned in and whispered, “That’s how you do it!”

Goorin Bros

The Goorin family has been in the hat business since 1895, and the store works hard to keep that feel: dark-stained wood floors, a velour-covered loveseat (so you can sit with a hat and get to know it, perhaps). We were just musing about how odd it is to see classic hat styles sitting atop young heads with tattooed necks and various piercings – something like watching Billy Idol working a butter churn or Pink at a loom – when we spotted it. Our hat. It’s brown tweed and it fits like a charm.

Haberdash

The large storefront on State Street will call you in with uncomplicated clothing that hints at the past: tweeds and wools, rustic pants and wrinkled shirts. We’re greeted like regulars by a man in a flat cap, suspenders and old-timey button-down, because as he explains, Haberdash values the best of times gone by. This is a place for gentlemen with gentle manners, an environment where a fellow can feel at ease shopping and shooting the breeze. As we consider a pair of Wolverine boots, we tell the man that we’d never before encountered a store that could make us want to extend the experience of shopping. Until now.

Green Mill Jazz Club

This 100-year-old jazz club seems like it’s never changed, with wild oversized paintings and Art Nouveau designs from floor to ceiling. Join the crowd drinking in all the jazz that wafts from the stage, from the bebop to warm-blooded Latin music – the performers always give it their all. We sipped on scotch and sodas and people-watched the jazz fans young and old. That’s the thing about this town: the past and present keep each other alive in every brick, in every saxophone note, and here at the Green Mill on a Saturday night, the horns blow until 5 a.m. The night is young.

Curio

Pass the heavy velvet curtain and you’ll feel like you’ve stepped into a preserved room from the 1920s, with dense leather sofas lining the walls and designer wood tables that somehow retain an overturned-orange-crate feel. Candlelit through thick jars, past the golden vintage cash register, sits the bar’s namesake, a curio: an ancient display case filled with glass jugs and strange bartending tools that look almost pharmaceutical. Our Pimm’s Cup – Pimm’s No. 1, ginger beer, lemon, cucumber, orange and mint – was so delicious, we wanted five. Way back when, the police would have raided a place like this, but today the only fuzz in this chic-easy is the egg white in the whiskey sour.


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Where to Stay

The recently renovated Allegro Chicago mixes Art Nouveau decor with modern design. When we were there, there was a mannequin at the base of the lobby’s elegant double staircase, painted pink and carrying a laser gun. (Think Cotton Club meets Stargate.)
171 W. Randolph St., 312-236-0123, allegrochicago.com

The Palmer House Hilton, the city’s grande dame, has perhaps the greatest lobby bar around, with Sistine Chapel ceilings and an afternoon tea that’s famous for a reason.
17 E. Monroe St., 312-726-7500, hilton.com

Where to Eat

The mecca of Jewish deli delights since 1942, Manny’s makes the best everything – from knishes to kishke. At David Burke’s Primehouse, you can choose your meat aged from anywhere between 21 and 75 days in the Himalayan salt-tiled aging room. Have you ever thought your meat tasted happy?
Manny’s 1141 S. Jefferson St., 312-939-2855, mannysdeli.com
David Burke's Primehouse 616 N. Rush St., 312-660-6000, davidburkesprimehouse.com

What to Do

Suit seekers looking for the latest cuts should head to Haberdash, but if it’s a hat you’re after, the ancient and jam-packed Goorin Bros. is the place for you.
Goorin Bros. 1533 N. Milwaukee Ave., 773-384-4287, goorin.com
Haberdash 1350 N. Wells St., 312-440-1300, haberdashmen.com

Opened in 1907, Green Mill Jazz Club made its name with headliners like Al Jolson, Eddie Cantor and Sophie Tucker. It remains Chicago's hopping house of jazz. Curio, on the other hand, makes the best Chartreuse cocktail around.
Curio within Gilt Bar, 230 W. Kinzie St., 312-464-9544, giltbarchicago.com
Green Mill Jazz Club 4802 N. Broadway Ave., 773-878-5552, greenmilljazz.com