2 Sisters

Spot for boutique shoppers on a budget. Spacious, well-lit shop packs a continuously revolving collection of thoughtful and chic pieces, but at the kind of prices you might expect to see at the mall, rather than in the West Loop. Vigoss brand jeans, cute styles by Peppe Peluso, Pinko 1988 and Biss Princess circulate the racks and the friendly staff make the experience a pleasurable one. You’ll walk out with more than you meant to, but without breaking the bank.

Vera Chicago

Spain is the influence at this West Loop wine bar helmed by husband and wife Mark and Elizabeth Mendez. Wine list is 100 bottles strong, and there’s artisanal cider and beer–but specialty is sherry, a rarity in the States. Dishes cover various regions in Spain, with options such as beef tripe with morcilla and garbanzos; paella with duck and rabbit chorizo; and cheese plates highlighting both Spanish and Midwestern favorites. Classy.

8 Fifty 8

Weekend-only dancing den in former Theatro space. Music’s too loud for chatting, so come to dance or down enough speciality cocktails till you can hear over Gaga and Katy Perry vibrating from the speakers. Easy to drown in a sea of form-fitting dresses and too tight denim. RSVP for easy entry, door staff equipped with iPads can easily double check your VIP status.


Great-looking space, all dark and fetching, with sconces that pull light up the walls with drama and reverence. After all these years, Italian mainstay and pioneer of the Randolph Restaurant Row is still happening. Nothing particularly innovative about Vivo’s menu, it’s just good food. It doesn’t hurt either that it has one of the most romantic nooks in the city: their celebrated elevator shaft.


On a Friday at 9pm or Tuesday at 6:45, this communal winebar/eatery is always abuzz. And no wonder. Co-owned by Chicago restaurant dynamo Donnie Madia (he of Blackbird, Sonotheque and Violet Hour), Avec is all casual cool. Stylish foodies settle in for salumi, fish specialties and exotic cheese plates paired with expertly selected vino.

Karyn’s on Green

As misnomers go, a gourmet vegan menu might be up there with social conservatism. But Karyn Calabrese (Karyn’s Raw and Karyn’s Cooked) dares you try her vegan interpretations of chorizo sliders, crab cakes, and crispy chicken legs and not be halfway converted. Aside from the upscale mix of cooked and raw dishes, Karyn’s offers a full bar and extensive list of fully sustainable wines in an atmosphere that’ll keep the college hippie in you completely comfortable, replete with a large communal table. Too crunchy for you? That’s okay, there’s a little market and carry-out area for those vegans who are still closeted.

Belly Q

Between Lillie’s Q, Porkchop, and a handful of others, Chicago has had no shortage of recently-opened barbecue joints. Not that that’s any surprise for a meat-and-potatoes-loving town. But chef/owner Bill Kim of Urban Belly and Belly Shack acclaim adds an Asian twist and classier environs to the culinary trend. DIY at a table grill at one of the wood booths or order off the menu, packed with everything from banana leaf-wrapped salmon, tea-smoked duck breast served with Chinese buns and goat milk feta cheese and rice noodle pancakes. And of course, Kim’s famous kim-chi. The bar shakes up craft cocktails, so you can ease into the night with some smooth sochu in your system before moving onto Thai fried chicken.

La Sardine

Companion restaurant to Le Bouchon, this restaurant’s brightly painted pillars and bustling dining room create a communal feel. Makes standing at the bar more intense because room is well-lit and it feels like everyone is staring at you. Jitters recede after being seated with a good cabernet and some snails Burgundy.


Paul Kahan is a James Beard Foundation award winner and the consistently huge crowds at this super sleek room bear it out. Emphasis on carefully prepared dishes that are arranged like artpieces, so much so that piercing one with your fork feels like a violation of something sacred. Prada-clad foodies and their Marc Jacobs draped dates dine on cleverly assembled game, seafood and veggie dishes. Brilliant.