Top City Vacations

The Ultimate Shoppers' Guide To Chicago

By , December 1st, 2014

As Chicago slowly appeared through my airplane window, my excitement grew for exploring the Windy City’s shopping offerings. Some people do museums, but I do sidewalk sales. Most travelers head straight to Michigan Avenue, otherwise known as the Magnificent Mile, for the large assortment of shops. To walk on this busy Chicago thoroughfare was exciting, but the retail shops were far from unique. So, it was time to put my fabulous explorer hat on and leave the beaten path. I was determined to find Chicago’s best shopping areas.


Wicker Park is for the indie-chic scene

Wicker Park

Photo by Joselito Tagarao CC BY

Visit Kokorokoko, a shop that is even more fun to visit than it is to pronounce. This vintage store is packed with 80s and 90s threads. Not retro enough for you? Head over to Labrabbit Optics, an optician that carries brand-spanking new vintage frames from as far back as the early 20th century. Don’t leave the neighborhood without visiting the classics: Reckless Records for your vinyl fix and Myopic Books, one of Chicago’s oldest and largest used bookstores. Lastly, make sure to be in town for the Renegade Craft Fair in Wicker Park, a large event serving the DIY craft community, perfect for one-of-a-kind handmade finds.

The Swedes in Andersonville

Windy Knitty

Photo by Sheila Sund CC BY

Here’s a little background information about Chicago’s thriving Swedish community. A century ago, Chicago had an important Swedish population concentrated in the Andersonville district. Today, it’s one of the city’s trendiest neighborhoods, very popular with the gay and lesbian community, especially. While most shops focus on vintage or Scandinavian-inspired home decor, there are strong fashion contenders to be found as well. Mr. and Mrs. Digz is a clothing store offering merchandise that is split in quarters: ¼ new, ¼ designer consignment, ¼ local designers and ¼ vintage. In the mood to create? Windy Knitty is a specialty yarn store that offers knitting space and classes for those not so familiar with the craft.

Shopping’s perfect for crummy weather

900 North Michigan

Photo by Roman Boed CC BY

It’s no secret that Chicago winters are unforgiving while summers can be uncomfortably humid. This is the perfect time to visit shopping malls and I can’t think of a better one than the shops on 900 North Michigan. This skyscraper is Chicago’s 8th tallest building and features an upscale mall spread out over seven floors. The more upscale tenants in the mall include Michael Kors, Gucci and Coach while Lululemon, Adidas and Bloomingdale’s keep the mall a bit more accessible.

Shop for custom-made and eco-friendly products

Custom-made threads

Photo by McKay Savage CC BY

Stroll over to West Town and you’ll wander into Chicago’s Ukrainian Village. This neighborhood was originally inhabited by Ukrainian immigrants, which were there to build mansions for their wealthy next-door neighbors in Wicker Park. Today, it is a more casual and family-friendly neighborhood. Greenheart Shop is a beautiful store that carries fair trade and eco-friendly accessories. If you’re looking for custom-made threads, Novem Studios is an independent graphic design team that offers silk screening printing, clothing and accessories.

Where do you like to shop when you’re in the Windy City?

*feature photo by Caroline Leal


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