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Haberdash Roosevelt Collection

The best shops in the South Loop

The growing neighborhood boasts a similarly growing indie shopping scene, including these top shops in the South Loop

By Laura Baginski
In the shadow of the Loop's skyscrapers, the South Loop is lousy with Chicago attractions—and residential towers. The people living in all those condo buildings and lofts need more than just Target for their shopping needs, and the neighborhood is starting to meet the demand with high-end liquor stores, bike shops and one of the city's best art-supply stores. These top shops in the South Loop are the seeds of a thriving shopping scene in the small but mighty neighborhood. 
RECOMMENDED: Our complete guide to the South Loop

South Loop stores

Artist and Craftsman Supply

Shopping Arts, crafts & hobbies Loop

The Chicago outpost of a small, national chain of art supply stores, this two-story shop carries hard-to-find supplies, unique gifts and funky novelties. Its knowledgeable staff comes in extra handy for those tricky art projects. 

Haberdash Roosevelt Collection

Shopping Menswear Loop

Each time this local menswear shop opens a new outpost, it seems to outdo itself. The River North location features hot lather shaves in the back of the shop, and this South Loop spot takes that feature and adds a barista-staffed lounge that features La Colombe coffee. Of course, the real reason men flock here is for the well-edited collection of clothing that includes items from Barbour, Gitman Vintage, Baldwin Denim and Haberdash Bespoke no.607, the in-house affordable line of made-to-order canvas suits.



Shopping Boutiques Loop

This Midwest-born urban boutique brings stylish street wear to the South Loop. Expect to find plenty of hip-hop and skater gear, as well as vintage apparel. Shop here for the store's namesake label, featuring men's shirts, hoodies, tees and beanies, plus other brands like Mishka, 10 Deep and Billionaire Boys Club.

Loopy Yarns

Shopping Boutiques Printers Row

A knitter's paradise, Loopy Yarns draws yarn fanatics from all over the city. You won't just find the most extensive yarn selection in Chicago, you'll also walk out with some major tips and tricks from its savvy staff, who offer an extensive series of workshops for all skill levels. You'll be knitting enough socks to start up an Etsy side hustle in no time. 


On The Route Bicycles

Shopping Sports Printers Row

Open since 1971, On the Route has expanded from its original Lakeview shop to two additional locations in Chicago. Brands available include Trek, Cannondale, Electra, Bianchi and more. Given that one of the owners is a female cyclist, On the Route stocks the shop with plenty of female-specific cycling gear. Stop in for tune-ups, accessory installation and more.

Printers Row Wine Shop

Shopping Liquor stores Printers Row

A family-owned establishment and sister shop to Little Italy's Gentile's, Printers Row Wine Shop is known for its rustic charm and selection of small-batch spirits, craft brews and wine from local distributors. As any good South Loop wino knows, it's the place to be on Friday night, when it offers free wine tastings from 5–8pm. Or, you could join the shop's wine club ($39.99 per month), and pick up a new, hand-picked bottle of red and white to try on the 15th of each month.

Sandmeyer's Bookstore
Photograph courtesy of Sandmeyer's Bookstore

Sandmeyer's Bookstore

Shopping Bookstores Printers Row

Located in the South Loop, this family-owned and -operated book shop has been in business since 1982. Step into the brick building and you'll find shelves filled with new releases, travel guides and books to keep you occupied on your train ride home.


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