Homestead on the Roof


1924 W Chicago Ave
Chicago IL60622
(773) 332-2354

Roots Pizza serves as a prime Ukrainian Village hangout for premium thin-crust pies, craft beers, and televised sports, but upstairs offers a completely different vibe. Homestead on the Roof serves up chef-driven fare and fancy cocktails, but thankfully it’s a very laid-back experience, making it perfect for date night. Roll in with someone special, and maybe another couple, like those neighbors you’ve always wanted to get to know better. If the weather’s favorable, grab an open-air seat. Homestead is the only rooftop patio in the nabe that also doubles as a full-size working garden. Don’t be surprised if you spot a cook—or bartender—picking fresh herbs or vegetables close to your table. Homestead is a farm-to-table restaurant in the most literal sense, so take advantage of the situation by ordering as many market-fresh dishes as possible. Start with a Little Gem Salad, an unconventional appetizer amped up with black barley, English peas, braised artichokes, and smoked Caesar dressing. If it’s a double date, break bread with those new neighbors by ordering a basket filled with laminated brioche, jalapeño cream cheese cornbread, and ciabatta served with olive tapenade, pickled veggies, and Oaxacan honey butter. While the menu is seasonal, you can always count on the kitchen to work smoked oxtails, seared whitefish, and grilled steak into a few dishes (all with local vegetables, of course). Raise a signature cocktail—maybe a rum with blueberry, thyme, and housemade falernum—and toast the transformation from neighbors to friends.

– See more at:

View Larger Map

Photograph by Peyri Herrera



108 W Kinzie St
Chicago IL60654

Mercadito may have originated in New York, but its Chicago location is a local standby. It makes an ideal spot for your next group outing for a bunch of reasons. For one, the menu changes regularly to reflect the tastes of the Mexican-born chef, which should please your pals looking for authenticity. Your foodie friends will dig the “celebrity chef” tacos, as each month, well-known local and national culinary stars put their spin on the popular street fare. But there are no wrong turns on the menu, since everything is lovingly made with market-fresh ingredients. Maybe you’ll find some adobo-marinated grilled chicken with bacon mojo and queso fresco, or dry-roasted pork belly with roasted apples. If you’ve got clubbier chums in tow, they’ll appreciate Double A, a “secret” subterranean tequila lounge below Mercadito. You can grab a few bites down there, but its main draws are Latin craft cocktails and DJs spinning exotic and soulful tunes. The tiny space accommodates only about 50, so if you don’t have a reservation, you’ll hang out at the bar. That’s actually the best spot in the room, as you can watch mixologists whip up specialty sippers with fresh fruits, offbeat spices, and, of course, some of the finest tequila in town.

– See more at:

View Larger Map

Photograph by opacity
Edited by MasterCard

Green Street Smoked Meats


112 N Green St
Chicago IL60607
(312) 754-0431

With so much barbecue in Chicago, it’s easy to find a place that does pulled pork well. But when you’re also looking for some atmosphere—and a supreme whiskey selection—you need to make a beeline for Green Street Smoked Meats in the West Loop. You know this is the place to go because you’re a fan of nearby sister spot Au Cheval, the contemporary diner where folks obsess over their irresistible, upscale, double-stacked cheeseburgers. Green Street gives a similar update to Texas roadhouse BBQ–but not so much that it’s too cool for school for your next guys’ night out. Guide your friends to the unmarked entrance through the alley on Green Street. Once you’re inside this bright, lively place, grab a craft beer, whiskey, or mezcal Negroni, and then head over to the quick-service food line. At the counter, you can order ‘cue from different regions: Carolina pulled pork, Memphis baby back ribs, and Texas brisket, just to name a few. Add perfect house-made sauces (mustard, sweet, spicy, vinegar) and sides (cole slaw, macaroni salad, spicy fries) and you’re ready to settle in. Grab a communal, picnic-style table in the dining room or head outdoors to the patio if the weather’s nice. The setting’s not half as rowdy as your typical roadhouse, so you’ll be able to hear each other as you get all caught up on the latest. (The soundtrack does crank out country tunes, but that just guarantees the energy levels stay high.) On your way out, show off your game on the miniature b-ball basket hanging over the door. After all, it’s been a night of slam dunks. One more seems about right.

– See more at:

View Larger Map

Photograph by jeffreyw
Edited by MasterCard

County Barbecue


1352 W Taylor St Chicago IL 60607
(312) 929-2528

You’re always looking for the perfect place to keep the party going following a big Bulls or Blackhawks win. Little Italy is only a five-minute ride from Chicago’s United Center, putting County Barbeque in easy reach for your next post-game get-together. Grab the round table in the center of the room and start off with some refreshing whiskey cocktails. An Old Fashioned (a classic featuring rye, bitters, sugar, and water), or a house special like the Cornbread Moon, with bourbon, bourbon-barrel-aged maple syrup, lemon, and allspice dram, will keep you smiling as you peruse the menu. Drinks in hand, get the food parade going with the infamous bacon-and-barbecue parfait: deep layers of cheddar grits, pulled pork, and bacon in a shot glass. (Seriously, how amazing does that sound?) You’ll be harder pressed to make your entrée choices when there’s veal brisket and smoked St. Louis-style spareribs on the menu. Fortunately, County makes decisions easier by offering a tasting menu that’s $18 per person. You’ll get the spareribs, plus Texas-style brisket, spicy hot links, and smoked chicken that you can drizzle with house-made barbecue sauces. Add a few sides (smoked pork hush puppies, seared kale, cheddar grits) and you’re all set. And don’t worry about your table being too loud, that’s encouraged here. Booming funk beats serve as a great soundtrack for festive occasions, like another W for Chicago’s own.
– See more at love this city

Photograph by jeffreyw
Edited by BlackBook



534 N Clark St Chicago IL 60654
(312) 595-1616

You’ll find Brindille completely different from Naha, its well-seasoned next-door sibling, the moment you walk in on date night. Instead of Naha’s opulent Mediterranean atmosphere, the French-focused Brindille opts for subtle sophistication and a bit of a vintage vibe. You’ll absorb that flavor from your perch at the bar as you and your sweetheart enjoy an aperitif before dinner. Muted tones and downtempo house grooves set a relaxed vibe as you settle in for the evening. While there are a mere five house cocktails on the menu, they’re all tempting, perhaps none more than the Vieux Carre, with its layered mix of rye, cognac, vermouth, and Peychaud’s Bitters. You’ll also have a meticulously curated offering of absinthe, amaro, ports, and whiskeys to choose from, if you’re a bit more of a purist when it comes to spirits. Once your table is ready–maybe you requested that special circular table in the rear–your little party of two will be ready to savor some of the city’s finest Gallic fare. You could go a la carte, but this might be the night to put yourselves in the chef’s hands with the tasting menu, which could include anything from foie gras and squab to lamb saddle. That way you can set your own pace for surprise after delicious surprise on an incredibly romantic night of fine dining in Chicago.
– See more at love this city

Photograph by jb
Edited by BlackBook

Au Cheval


800 W Randolph St Chicago IL 60607
(312) 929-4580

Once you get over the fact that you just waited an hour to sit down for a burger, you will appreciate Au Cheval for what it is: an ideal spot for a gathering with friends. This cheery, contemporary diner offers booths roomy enough for eight people, and you’ll appreciate the elbow room once the food arrives. You and your crew will be feeling the groove as you nod your heads in unison to old-school hip-hop, soul, and rock, cranked out effortlessly from vintage reel-to-reel equipment. About that burger? It’s simple enough, but griddled to perfection, with a generous two patties and American cheese when you order a “single,” and three patties when you order a “double.” Got that? Also popular is the stacked, Dagwood-style fried bologna sandwich that will take you back to the days when Mom packed your lunchbox. It’s so massive that you could slice it up and share it among your table. The bar specializes in classic cocktails, so order something appropriately old school. Your whiskey-lovin’ pals will appreciate the attention to detail put into the Old Fashioned, while the more adventurous types in the circle might indulge in a gin-based Pegu Club. The kitchen stays open late, so you can pair your drinks with more food, should this turn into a late night.
– See more at love this city

Photograph by Jennifer Woodard Maderazo
Edited by BlackBook



218 W Kinzie St Chicago IL60654
(312) 624-8154

While most Chicago steakhouses cater to over-indulgent business types, Bavette’s puts its focus squarely on date night. You’ll quickly find yourself feeling intimate and cozy on either level of this Parisian-inspired eatery, enjoying the dimly lit atmosphere among other well-coiffed couples. Head straight for the lower level, where you’ll find the best seats in the house. If you’re lucky, you’ll also rub shoulders with a visiting celebrity or two. The music upstairs majors in modern fare, but downstairs gets down ‘n’ dirty with velvety hip-hop, soul, and funk. There’s no dance floor, but the grooves will put you in the mood for a little bump and grind, and you’ll enjoy the energy of mingling with like-minded couples. On the dining side, the menu caters to steak and seafood lovers. Set the mood by feeding each other from the plateaux de fruits de mer, a bountiful platter of fresh lobster, oysters, clams, mussels, and more. If you’re in steak mode, the prime bone-in filet cannot be missed. It’s a solid 16 ounces, perfect for sharing, accompanied by a decadent Béarnaise and steak salt. Alas, it’s in limited quantity, so you may want to come on the early side. To completely embrace the French steakhouse theme, toast your night with sparkling cocktails, ranging from the absinthe-based Death in the Afternoon to a classic Kir Royale.
– See more at love this city

Photograph by
Edited by BlackBook



111 W Hubbard St Chicago IL60654
(312) 828-9000

Celeste’s glamorous Deco Room is the type of late-night sanctuary you’ll want to hide out in with someone super-significant. Reserve the tiny table for two at the top of the room and you’ll feel like you’re the only ones in the space. Add to that intimate experience a carefully curated cocktail menu, designed exclusively for the lucky patrons on this second level. Be bold in your choices, as the adventurous elixirs served in this clandestine lounge make use of exotic ingredients like crema de mezcal infused with chocolate and chili. A flavor profile is included under each cocktail, so you can concentrate on the beautiful face before you instead of asking your server a million questions. Savor the anticipation as you get ready for something that’s “smoky, layered, orange,” “herbal, mint, sophisticated,” or “savory, Nordic, esoteric.” Most cocktails have been prepped to pair with a seasonal menu of light bites with an emphasis on seafood. You’ll find that the romance of this dining and drinking experience is strategically tied in with the smooth music on the second level. While the first floor throbs with hip-hop, house, and pop hits, the upper level embraces a more sophisticated vibe, offering old-school soul from the likes of Diana Ross and Minnie Riperton. When you really start feeling the music, take advantage of your secluded little corner and dance a little.
– See more at love this city

Photograph by Gabriel Saldana
Edited by BlackBook

Park Hyatt Chicago


800 N Michigan Ave Chicago IL60611
(312) 239-4030

If you’re planning a family getaway in Chicago, a long weekend at the Park Hyatt on the Near North Side is fantastic all year round. The hotel’s central location in the city’s most vibrant neighborhood makes it perfect for when your kids want to play all day at American Girl Place across the street, or take in the sights from a horse-drawn carriage. When you need a break, one of the best places in the area to eat is right inside the hotel. NoMI’s a grown-up spot, but your kids will feel right at home in the summertime with the make-your-own-sundae program. You’ll love watching their dessert dreams come true as they pick and choose among house-made butterscotch, graham streusel, and peanut butter fudge. Or say they’re all bundled up and coming out of the cold during winter. The pastry team’s got their back with creamy and thick hot chocolate that’s certain to please every little one—and big one—in the group. More house-made toppings, like mint-infused marshmallows and flavored whipped creams, take hot cocoa to a new level. And just in case you were wondering, while everyone else is picking out all sorts of crazy toppings, you can have yours spiked with a nip of whiskey, rum, or Grand Marnier.
– See more at love this city

Photograph by Zechariah Judy
Edited by BlackBook