Supporting the small businesses that make Chicago a one-of-a-kind city is more important than ever this year. And holiday season is the opportunities to make a positive impact with your gift shopping.

Whether you mask up and shop in person or stay at home and shop online, choosing to invest in Chicago’s small businesses is a meaningful way to spread holiday cheer and support your favorite local places.

Here’s some shopping inspiration around Chicago’s neighborhoods to get you started:

Ravenswood & Andersonville

Photo by Thomas Bock

These nearby neighborhoods are home to some of a close-knit small business communities that are bound to have something for everyone on your list.

In Ravenswood, the Chamber of Commerce is putting together themed surprise gift boxes with goods from more than a dozen local businesses including Starshaped Press, Lena Rose Beauty and The Chopping Block. Another great gift idea: pick up six-packs and gifts cards from the neighborhood’s many breweries.

Photo by Lindsay Lenard

In Andersonville, shops will be staying open later during the annual Late Night Andersonville  — only this year you can take advantage of order-ahead curbside pick-up so you can stay in your car (and your pajamas).

Browse for gifts online from Women and Children First bookstore, Jameson Loves Danger pet shop, Indigenous Artworks jewelry and clothing, or Mercantile M antiques.

Hyde Park

Photo courtesy 57th Street Books

Take the guesswork out of finding age-appropriate toys for your family with Toys Et Cetera’s curated lists of gifts for every age group. Or stock up on graphic novels, comics, and games for winter with a trip to First Aid Comics

57th Street Books is another neighborhood gem, and while the storefront is currently closed, the website is open for browsing. Or visit local favorite, The Silver Room, for unique art, books, jewelry, apparel, and more.

Rogers Park

Rogers Park is filled with fantastic spots like Rogers Park Provisions for cute kitchenwares and specialty grocery items or Homegrown Wrappings Gift Company for cards and gift baskets. And don’t skip women-owned XO Marshmallow, which will be selling their popular marshmallow advent calendars this year.

The neighborhood is offering special discounts and promotions both in-store and online from Nov. 28 through Dec. 31, including rebates to shoppers who patronize independently owned businesses in Rogers Park during the holiday season.

Lincoln Park & Lakeview


Lincoln Park and Lakeview are known for their vast array of locally minded shopping options. Your pants may not fit after the holidays, but a leather tote from Laudi Vidni always looks good. The shop’s name (“individual” backwards) also applies to its mission to create custom leather works of art for everyone. 

Terry’s Toffee on Armitage uses a recipe that originated with Terry’s grandma, so you know it’s a winner. Their treat boxes make excellent host gifts. For stocking stuffers, Inkling and Foursided specialize in small treasures and handmade cards for everybody on your list. 

Wicker Park & Bucktown
©Adam Alexander Photography 2019

If you’re looking for some new territory for quarantine walks, check out Wicker Park and Bucktown from Nov. 28 – Dec. 28 for the second annual Window Wonderland, where businesses decorate their windows and offer special deals to holiday shoppers. 

While your admiring the artwork, stop into Transit Tees for Chicago-themed apparel and gifts, Gemini for trendy clothes and jewelry, Una Mae’s for vintage clothing and fancy apothecary gifts, or Komoda online for a quarantine-friendly personal shopper experience.

The Magnificent Mile

Clayton Hauck for Choose Chicago

The Magnificent Mile is definitely a hotspot for holiday shopping — and not just at chain retailers, either. There are plenty of unique spots to explore.

Galt Baby has more than 35 years experience in stocking modern, fancy, and fun baby gifts and gear. Water Tower Place and The Shops at North Bridge are filled with shopping options and holiday gift possibilities. And Mary Mary Gifts offers unique homewares, art, and global gifts that make it a must-stop shop for locals looking for something truly special.