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Chicago shopping spans across many neighborhoods and includes everything from mass market fashion to local boutiques to high-end designer. Whether you're stopping in for the weekend or a resident looking to check out a different part of town, here's a guide to shopping in Chicago.
· A is for Asrai Gardens
This enchanting shop in Wicker Park has a lovely selection of flowers and small artisan goods like soaps, candles, jewelry and cards.
· B for for Belmont Army
An army surplus store in Wicker Park and Lakeview might seem a little strange. Those who have stopped in before know that among the troves of olive green and camouflage there are some vintage gems and a collection affordable apparel from contemporary brands like BB Dakota and RVCA.
· C for Comfort Me Boutique
As the name would suggest, this Lincoln Park boutique is a relaxing place to shop, full of soft textiles and cozy furnishings. The clothes are comfortable, on-trend and generally affordable. We're especially big fans of their eclectic jewelry selection.
· D for Donut Break
If you're shopping along Damen Ave in Wicker Park or Armitage Ave in Lincoln Park, you can treat yourself to a donut break at Stan's Donuts or Glazed & Infused. They're a crime against crop tops, but they're just so good and who doesn't love donuts?
· E for Eskell
This shop is a Wicker Park landmark. Eskell was once one of our favorite lines until they wrapped up in 2011, but they continued on with their boutique. The shop carries both vintage and new womenswear from an array of designers from across the globe and unique pieces you won't find anywhere else.
· F for Fleur
Specializing in exotic varieties and contemporary styles, Fleur is one of our favorite shops in Logan Square. It's a wonderful place to pick up flowers or gifts for a friend.
· G for Green Goddess Boutique
This sustainable-minded boutique is a local favorite with three locations - Bucktown, Lincoln Park, Hinsdale. If you're looking for some boho chic clothing, shoes, or accessories, you'll love this shop.
· H for Haberdash
Tweed ties, suede chukkas, and tailored jackets, these are just a few of the things you'll find at the dapper, heritage-inspired Haberdash. This menswear shop has two locations on State St and will soon add a South Loop location at The Roosevelt Collection to the list.
· I for Ikram
The New York Times has described owner Ikram Goldman as the high fashion ambassador of the midwest. Alexander McQueen, Celine, Chanel, Maison Martin Margiela, Rodarte, this upscale boutique is what dreams are made of.
· J for Jayson Home
This high-end home store is incredibly well curated. With beautiful displays made of modern and vintage gems, there's no other store in Chicago quite like it.
· K for Krispyfringe Vintage
Located in West Town, Krispyfringe carries vintage mens and womenswear from 1940s to the 1990s. It's a fun stop for the vintage-obsessed.
· L for Lori's Shoes
This Lincoln Park boutique is for the shoe obsessed. The shop is always on trend and carries styles at all price points from the likes of DV by Dolce Vita, Jeffrey Campbell, Frye, Zadig & Voltaire, and specialty brands we've never even heard of!
· M for Moon Voyage
If you follow New York, Los Angeles or Australian style bloggers, you'll especially appreciate this beautifully curated boutique. Moon Voyage is full of unique pieces from small labels around the world that are effortlessly edgy and chic.
· N for A New Leaf
Some might know this shop as an flower shop or an event space, but we think of as a treasure trove of candles, tiles, ribbons, and vases for the home. Whether you're looking for a big center piece or something small to spruce up your home, you have a good chance of finding it here.
· O for Open Books
Shop for books and support a nonprofit social venture that provides literacy. It's a beautiful thing!
· P for Penelope's
If you prefer having classic staples to trendy pieces, you'll love this Wicker Park shop. The aesthetic is mix of Brooklyn and Parisian chic, and they carry clothing and accessories for both men and women.
· Q for Quick Stop
If you don't have the time to leisurely stroll through a neighborhood, then consider popping into a shopping center like 900 N Michigan or Water Tower Place where you'll find dozens of retailers.
· R for RSVP Gallery
With clean white walls and neon signage, this hip Bucktown boutique indeed feels like a gallery. It's a great place to shop for lux menswear and accessories with street cred.
· S for Space519
This "refined general store" at 900 N Michigan is a staple in designer shopping. This boutique carries everything from apothecary items and books, to men and womenswear from the likes of Jil Sander, Rachel Comey, and 10 Crosby.
· T for Trunk Club
For the men who like shopping from home, there's Chicago-based Trunk Club. The stylist-driven service makes it super easy to shop. Chat with a stylist, receive a trunk, try on and keep or return to your liking.
· U for Una Mae's
Located in the heart of Wicker Park, this boutique is great for both men and women looking for hipster-esque threads.
· V for Vintage
Every neighborhood has a vintage shop or two, but in Pilsen, there are vintage shops all along 18th Street. Two of our favorite shops in the neighborhood are Dethrose Vintage at Market Supply Co and Knee Deep.
· X for exhale Spa
Sometimes all you really need is a little R&R. Located in Gold Coast, you can schedule a spa treatment for after shopping along Oak Street.
· Y for Helen Yi
With an eye for the season's hottest trends and pieces with staying power, Helen Yi has an incredible collection of designer goods. Stop in to shop brands like Barbara Bui, Derek Lam, and Costume National.
· Z for Zara
Sometimes a girl just needs a little fast fashion. With a location along Michigan Ave and one in the Loop, Zara is an easy and affordable place to shop the latest trends.
· The Ultimate Miami Shopping Guide, From A to Z [Racked Miami]
· Do You Know the ABCs of Shopping in San Francisco? [Racked SF]
· The ABC's of New York City Shopping [Racked NY]
· A Handy Guide to Shopping in Los Angeles, From A to Z [Racked LA]