Chicago Written by Amy Crist
Located on trendy Armitage Avenue in Lincoln Park, this exquisite shop features women’s clothing and fashion accessories as well as gifts and home accessories to fit a vast array of personal styles. You’ll find the perfect outfit to have you sparkling in Lincoln Park after dark. (Sorry, we couldn’t resist.)
934 W. Armitage Avenue, Chicago, IL
Asrai Garden is owned by a true Chicagoan who expresses her emotion through her exquisite floral arrangements. Elizabeth Cronin gathers loose stems and displays them to look like a handsome suitor left a bouquet on your doorstep.
1935 W. North Avenue, Chicago, IL
We secretly wish we might see Don Draper strutting through this store. This dapper destination is the perfect place to find items that will help you drink, smoke and lounge in 1960’s style. Brimfield’s home finds drip Rat Pack swag like no other.
5219 N. Clark Street, Chicago, IL
You know that girl who always has the best outfit at the party? She got it here. Edgy classics like Sass & Bide capes, sequin chevron jackets and buttery leather shorts share space with lucite trays and neon jewelry.
1917 N. Damen Avenue, Chicago, IL
Walking into this art gallery and home store feels like you’re stepping into a Mad Hatter’s dream. This store is full of unique, quirky, and artsy pieces that are as outrageous as boutique owner Joan Cusack (yes, her). Cusack’s house of curiosity will have you smiling from ear to ear. Be sure to play nice with the elephant statue as you walk in.
1151 N. State Street, Chicago, IL
Neighborly is the midwesterner’s take on well-designed and affordable goods of mid-century modern style. Many of the items are sourced locally and feature the utmost in quality and quirkiness.
2003 W. Montrose Avenue, Chicago, IL
The Swett sisters grew their once-tiny shop into Chicago’s best stop for hand picked gifts, indie-designed greeting cards, and sweet little treasures. Stock up on journals, letterpress stationery, and hand-selected children’s books.
2027 W. Division Street, Chicago, IL
Imagine vintage hotel silver, sweet notebooks imported from France, and even monogrammed aprons. Once we shipped home a whole set of silver-rimmed dishes, service for 8. Ah, the things we do for love.
613 N. State Street, Chicago, IL
Roost is an extremely well-curated vintage store that will have you lusting over place-settings for 12. Their unique home finds are an obsessive collector’s dream come true. We’re still kicking ourselves for not bringing home the firehouse chairs.
5634 N. Clark Street, Chicago, IL
This rustic and romantic space not only features beautiful hardwood floors, exposed brick walls and filament lightbulbs, it also features the best emerging and established designers. Roslyn has an exquisite selection of dresses from designers including Alice + Olivia, Elizabeth and James, and Porter Grey.
2035 N. Damen Avenue, Chicago, IL
A word to the wise fashionista: pack an extra suitcase or two. SARCA is Chicago’s premier mecca of hip designers. You’ll walk out with an outfit ready for a night in Chicago’s chic meat-packing district. The accessories and shoe selections offer further temptation.
710 N. Wabash Avenue, Chicago, IL
Nestled in the heart of Gold Coast, this eclectic boutique features a hand-picked collection of clothing, shoes and accessories. Sofia was named after a true fashion icon — Sofia Loren, and exudes similar beauty, class, and glamour.
100 E. Walton Street, Suite 106, Chicago, IL
The Painted Lady
In the heart of Bucktown (the architectural salvage district du jour), this gorgeous store is sure to make your heart skip a beat. The owners scour Midwestern flea markets and estate sales for pretty chairs, vintage lighting, and all of those things that give a home character. From antique boudoir finds to beautiful dining tables, you’ll want to bring home every piece you find.
2130 N. Damen Avenue, Chicago, IL
Food + Restaurants
Antique Taco boasts “market Mexican fare, drink-worthy cocktails, and old antiques,” and this trifecta of bliss should not be missed. Order the habanero popcorn and fish tacos and sit back and enjoy this mason-jar friendly establishment.
1360 N. Milwaukee Avenue, Chicago, IL
Graham Elliot has taken rock-n-roll and food and turned it into a religion known as GEB. Menus are served on old vinyl records and the staff is as hip as they are friendly. The restaurant features bright red hues and is lined with tongue-in-cheek saint candles featuring the likenesses of Elliott’s chef friends.
841 W. Randolph Street, Chicago, IL
Girl And The Goat
There’s a lot to love at Stephanie Izard’s uber-hot restaurant: soaring ceilings, polished wood tables, the glistening bar. And then there’s the food. Izard has been dubbed the “architect of flavor” and her menu features duck confit, diver scallops, and Kona Kampachi Crudo – crispy pork belly with chili aioli and caper berries. If you can’t get in for dinner, have cocktails at the bar.
809 W. Randolph Street, Chicago, IL
Hoosier Mama Pie Co
This artisanal pie company has brought back some old-fashioned favorites in a big way. This sweet little pie shop features a slice and a cup of joe for $5 or stop in on a Friday night to enjoy a “Pie Flight” of three slices. Pure pie heaven in a slice (or three).
1618 W. Chicago Avenue, Chicago, IL
Hub 51 is the hub of Chicago, so to speak. Located on Hubbard just off Michigan Avenue this local establishment is constantly packed with stylish Chicagoans. The cocktails and snacks are as lively as the atmosphere and the extensive menu has something for everyone.
51 W. Hubbard Street, Chicago, IL
Pops For Champagne
This darling bar is steps from Michigan Avenue and is by far the best place to rest those tired feet from a full day of shopping. With over 200 champagnes and sparkling wines by the glass as well as delicious snack plates, you’ll quickly get an energy boost to tackle the boutiques off nearby Oak Street.
601 N. State Street, Chicago, IL
Publican is in the heart of the hot meat packing district for a reason. The sprawling community table winds through the restaurant and will have you quickly befriending your neighbors. The private tables are a mock “pig pen” leaving you completely enclosed for a private dining affair. We always leave with full tummies and big smiles.
837 W. Fulton Market, Chicago, IL
Chef Art Smith is the papa bear of Chicago. His warm and comforting dishes taste like Sunday dinners at home. Tea-braised short ribs fall apart at the first touch of a fork. For more of Art’s love, order the cauliflower, gruyere, mushroom, brown butter crumble. The only thing you’ll regret is not ordering two.
52 W. Elm Street, Chicago, IL
The J. Parker
Sitting above the Hotel Lincoln, the J Parker was named after President Lincoln’s bodyguard. This small yet fashionably hip lounge offers unobstructed views from a large terrace. Order small plates and sip elegant yet unfussy cocktails. The Parker Collins is our favorite.
1816 N. Clark 13th Floor, Chicago, IL
This quiet little neighborhood spot boasts exposed brick walls, beautiful lighting and clever menus. It is the perfect restaurant to enjoy in the company of dear friends after a long day shopping. The cheese plate is a work of art, and the wine menu is dreamy. Order the Spaghetti Frutti di Mare: an aromatic blend of sauteed clams, black mussels and shrimp in a spicy white wine tomato sauce.
838 W. Randolph Street, Chicago, IL