Chic in Chicago: the best places to shop in the Windy City

08 Jan 2021 | Travel
img tempus
* Image Source: Pexels

Chicago is famous for its Chicago-style hot dogs, Chicago-style deep-dish pizza, jazz music, and 1920s gangsters. There’s also plenty to do, like visiting Millennium Park and the Willis Tower (check out some of the best ideas in this article on Viator.) Chicago was also a hotbed for fashion before New York took that trophy, but don't discount their incredible boutique shopping district. There are plenty of excellent places to shop in the city, including the following.

Hyde Park

If you're looking for the best things to do in Chicago, start at Hyde Park. With the incredible landscape framed by the University of Chicago Campus, the community is famous for its restaurants, locally-owned shops, and numerous used book stores. 57th Street Books has titles that include academic works and fiction and plenty of events run by authors.

Dearborn Denim is an interesting store that offers jeans that are cut and crafted in front of you, which produces a product that will last for ages. Toys Et Cetera has plenty of games and toys that are fun for children and adults. Finally, the SIlver Room includes artwork, clothing, accessories, and jewelry to complete any outfit.


The historic Swedish neighborhood is filled to the brim with friendly local bars, diverse food choices, and a unique shopping district. Let's start with Alley Cat Comics, which is a pop culture paradise for most geeks. Then there's Hopleaf, which offers a wide range of beers on tap and incredible food. The Coffee Studio is rated the best coffee shops in the city, so take a look.

Nature types will love the Gethsemane Garden Center because it features plenty of seasonal plants and flowers throughout the year. If you're interested in history, take a trip to the Swedish American Museum, where you can learn about Swedish immigration to Chicago. Once done, visit Women and Children first to support women authors around America.

Lincoln Park

You can spend multiple days shopping at Lincoln Park and never get bored because of the variety of stores. Halsted Street and Armitage Avenue area is especially famous for its shops that sell art, gifts, and designer shoes. Art Effects is one of the most popular of these because of its affordable section of women's accessories, jewelry, and clothes.

Writers will love the shop All She Wrote, which offers stationery, journals, cards, and coloring books you can fill out while on a subway ride. If you're into custom clothing, visit Laudi Vindi (individuality spelled backward) for their selection of accessories and leather bags that they will make for you and ship to any location in two weeks.


Lakeview is known throughout Chicago as an electric mecca filled with music and LGBTQ+ shops that will fill your senses with wonder. Although Lakeview is most known for theater and less for shopping, that doesn't mean you can't stumble upon some exciting finds. For example, Waxman Candles handmakes candles inspired by Chicago neighborhoods.

The Wiener's Circle is another experience you shouldn't pass up. They have incredible hot dogs and a playful staff that like to ridicule their customers (really, it's a great experience). Coffee lovers will be interested in Heritage Bicycles, which also sells fancy bikes. Cubs fans will also love Wrigley Field, which sells premium baseball merchandise.

Bucktown/Wicker Park

The Wicker Park and Bucktown districts are filled with vintage shops and boutiques you won't find in the Greater Chicago Area. Places like Transit Tees, Shuga Records, and Reckless Records create a market full of music lovers that want to wear their merch on their sleeves. Even Volumes Bookcafe keeps this theme while also offering great caffeinated beverages.

Asrai Garden is probably the most unusual shop in the area, as it offers taxidermy, jewelry, and flowers at a cost-effective price. After shopping, check out Wicker Park (the actual park), the 606, and Holstein Park for some incredible scenery. Music venue lovers will also appreciate WhirlyBall, Subterranean, and the Hideout.