Soho House Chicago
You don't need to have a membership to enjoy a stay at Soho House Chicago, but it certainly doesn't hurt. The newest member of the Soho Group, which runs 12 houses in places like Berlin, Miami, and London, this new establishment offers tiny, small, medium, and medium plus bedrooms to non-members, with guest status granting them access to the club's bars, restaurant, spa, screening room, and rooftop pool. Should you feel like becoming a member — potential members are vetted and normally come from creative industries — you'll also get access to the drawing room, library, and 15,000 sq ft gymnasium, and, depending on your membership, will be welcomed at all other Soho Houses worldwide.
Green City Market
Most farmers markets are "green" in concept — you're likely buying products directly from farmers and artisans, as opposed to them sending their wares to the store — but few take it as seriously as Green City Market. Open in the south end of Lincoln Park on Wednesdays and Saturdays from May until October (and in the Peggy Notebaert Nature Museum in the winter), this unique market offers local, sustainable foodstuffs from purveyors that are heavily vetted before being allowed in. The result is fresh, delicious food that you can feel good about eating.
Green Mill Cocktail Lounge
Yes, it has live jazz. Yes, it serves up tasty cocktails. Yes, it has a statue of Ceres in the corner. But you're not heading to the Green Mill Cocktail Lounge for any of that. You're heading there because of its history. Opened in 1907, the Green Mill was a favorite hangout for Al Capone and his henchmen, thanks to its dark atmosphere, and, legend has it, a series of tunnels underneath the joint that gave them a way to slip out of the bar unnoticed should the Feds stop in. You can even sit in Capone's favorite booth — with views of both entrances — but, unfortunately, the tunnels are off limits.
Big Star
Few things go together to create a great summer evening out like great food, good drinks, and terrific outdoor atmosphere. Big Star checks all three of the list. The simple menu includes a variety of tacos and tostadas, as well as grilled jalapeños, queso, salad, beans, and, of course, chips and guacamole, while the booze menu encompasses a solid selection of beers, an extensive bourbon list, an impressive variety of tequilas and mezcals, and a simple cocktail menu divided up into bourbon- and tequila-based drinks. Best enjoyed on the killer patio.
Joe's Barbershop
Don't expect to find any frills, facials, massages, or other unnecessary nonsense at Joe's Barbershop. Established in 1968, the shop is — for better or worse, but we think better — essentially unchanged since it moved to its current digs in 1985. Offering haircuts, shaves, and nothing else, this Logan Square institution is run by the shop's namesake and his son — fittingly named Joe Jr. — and prides itself on great conversation and friendly service dished out on a first-come, first served basis.
Firkin
The hamburgers are fantastic. The decor is eclectic, rich, and inviting enough that you want to stay all day. The staff is knowledgeable and friendly. But you're not heading to Firkin for any of that. Instead, you're making the trip to this little spot north of Chicago for the top-notch beer selection, which includes one cask, thirty one draught, fifty-six bottle, and six can options that range from everything from rare microbrews to a healthy selection of Belgians. If, for whatever reason, you're not feeling a beer, they also offer a small selection of wines as well as a full bar.
The Purple Pig
"Like father, like son" goes the old saying — and that's certainly true at The Purple Pig. Helmed by Chef Jimmy Bannos Jr. — with guidance from his father (of Heaven on Seven fame) and Scott Harris (of Mia Francesca), this Magnificent Mile serves up "cheese, swine, & wine" with a distinct Mediterranean flair. Highlights include the house-made charcuterie, the pork neck bone rillette, the scallop spiedini, and the Panino con Nutella. Not feeling hungry? It's still worth stopping by, as the Pig also happens to offer one of the best wine bars in the city.
Hala Kahiki
As far as Stateside Tiki bars go, it's tough to get more authentic than Hala Kahiki. Originally opened in 1963 as a neighborhood tavern, transformed into a Tiki not long after, and subsequently moved to its roomier current location, this classic Polynesian-themed bar offers over 100 tropical drinks on its extensive menu, as well as a full bar and a smattering of bottled beer. There's plenty of seating — 40 tables plus the bar inside, and another 15 tables in the garden outside — from which you can take in the terrific decor, including the largest collection of Witco art of any Tiki bar in the US.
The Belmont Barbershop
You won't be getting a manicure at The Belmont Barbershop. Nor can you order up a facial treatment, or lie down for a massage. But what you can get is a fantastic haircut. In business since 2005, this Roscoe Village haunt accepts appointments and walk-ins alike, and is staffed by six licensed barbers that are great at one thing: cutting hair. They also offer straight razor shaves. And that's it — but that's really all you need.
The Oregon Trail Burlesque
Okay, so there wasn't ever really anything sexy about the Oregon Trail, but the Gorilla Tango Burlesque troop is aiming to fix that with The Oregon Trail Burlesque: You Have Died of Sexy. Scheduled to run every Friday night in Bucktown from January 10 to April 11, 2014, this show mixes elements of the original computer game with a film noir-style murder mystery, all performed by lovely, scantily-clad ladies. It's obviously 18 and up, but at least you don't have to worry about contracting dysentery.
Telegraph
Sure, it serves food — very good food, in fact — but you don't make a trip to one of the country's best wine bars just to eat. Led by Sommelier Jeremy Quinn, Telegraph is a Logan Square establishment serving up a highly curated selection of wines focused rare and European offerings, with over 20 available by the glass. There's also a similarly well-considered selection of beers on tap, a handful of specialty cocktails, and a $35 three-course dinner that's far more impressive than its price suggests.
Roost
If you're expecting to find chicken coops and other farm-related items at Roost, you might be disappointed. But then again, you might not. This killer Andersonville vintage store stocks all sorts of items, from carefully-curated and displayed knick knacks on the first level to a full on retro furniture explosion on the second level. The prices aren't cheap, but neither is spending all weekend driving around to yard sales trying to find just one thing worth buying. Trust us. We've tried. And the only thing worthwhile we ever seem to bring home is a six-pack to calm our nerves.
