Chicago’s neighborhood are overflowing with shopping options, making them the perfect place to discover one-of-a-kind gifts for everyone on your list. You could spend days exploring all the unique boutiques, specialty shops, artisan markets, curated vintage sellers, and so much more. Plus, many neighborhood retail districts will be hosting special events and deals throughout the holiday season.

Whether you’re celebrating Small Business Saturday or just looking to knock out your gift list, these Chicago neighborhoods are the perfect places to shop during the holiday season — and all year round.


Photo by Thomas Bock

The Andersonville area, considered Chicago’s “shop small” capital, offers the perfect mix of charming and cool. You’ll find tons of gift options, like top feminist titles at Women and Children First bookstore, clothes and jewelry at Milk Handmade, the latest comics from AlleyCat, Chicago-centric items at Transit Tees, and on-trend decor and accessories from Foursided.

In the heart of the neighborhood’s retail corridor, the Andersonville Galleria is a one-stop shop for gifts that will wow. This multi-floor marketplace carries art and handmade wares by more than 100 local vendors, from gourmet treats to apparel to home furnishings. 

The neighborhood hosts an array of holiday events, including a holiday market at the Swedish American Museum, Hanukkah candle lightings, and a holiday trolley for shoppers. Don’t miss Dine & Shop on Fridays in December, with specials from local restaurants and shops.

Hyde Park

Photo courtesy 57th Street Books

Hyde Park, home to the University of Chicago, is known for its tight-knit community, locally owned businesses, and stunning gothic architecture. It’s the perfect combination for a holiday weekend in the city, when you can explore the wealth of shopping options throughout Hyde Park.

Take the guesswork out of finding age-appropriate toys for kids 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, with tons of titles from sci-fi to cookbooks to bestsellers. Or visit local favorite, The Silver Room, for unique art, books, jewelry, apparel, and more.

In December, check out some of Hyde Park’s holiday events like a gift market and family-friendly activities.

Rogers Park

The diverse lakefront Rogers Park enclave is filled with fantastic spots to shop for the holidays. Check out Rogers Park Provisions for cute kitchenwares and specialty grocery items orMalliway Bros. for spells, charms, and other witchy items.

And don’t skip women-owned XO Marshmallow, which will be selling an array of sweets and their ultra-popular marshmallow advent calendars this year.

Lincoln Park


Lincoln Park is a charming Chicago neighborhood that’s filled with vintage buildings, cozy wine bars, and award-winning restaurants. Pair that with a variety of unique local shops, and you’ve got a winning combination for holiday shopping.

The area around the Armitage Avenue and Halsted Street intersection is the perfect home base for your shopping extravaganza. Stop by Art Effect for one-a-kind kitchen and decor items, Monica + Andy for ultra-soft baby clothes, and the Chicago Bar Store for all the cocktail aficionados in your life.

When in doubt, a customized bag from the leather experts at Laudi Vidni is always a perfect gift. The shop’s name (“individual” backwards) refers to its mission to create custom wearable works of art for everyone’s unique style. 

Explore more: Discover even more gifting options at Chicago’s charming holiday markets.

Pilsen and Little Village

A colorful candy store in Little Village
Photo by Lucy Hewett

Pilsen and Little Village are both known for their Hispanic heritage and community of family-owned businesses, and the holidays are the perfect time to get out there and explore the array of fun shopping options.

Fill your loved one’s stockings with sweets from Dulcelandia. Find best-sellers and local authors at Pilsen Community Books, new and used vinyl from 606 Records, and authentic Mexican accessories and clothing from Artesanias Elena. The National Museum of Mexican Art also has an amazing gift shop with colorful art objects and unique finds.

Don’t miss the Annual Pilsen Christmas Window Walk, when shops pair with local artists to design and decorate their storefronts with holiday-themed displays.

Wicker Park / Bucktown

Adam Alexander Photography

The Wicker Park/Bucktown neighborhoods are known for their eclectic cool, where the streets are overflowing with buzzing bars, trendy restaurants, and colorful street art.

If you’re in the mood to shop, check out Gemini for trendy clothes and jewelry, Una Mae’s for curated accessories and fancy apothecary gifts, and a maze of used titles at Myopic Books. The area is also known for it’s great thrift stores and vintage shopping — check out Vintage Underground, Kokorokoko, and Store B Vintage.

Keep an eye out for holiday events throughout the season, like a pop-up artisan market inside The Robey and free rickshaw rides for neighborhood shoppers.

Logan Square and Avondale

Avondale Bowl
Avondale Bowl; photo by Sean Henderson, @theseanhenderson

Logan Square and Avondale are two hip neighborhoods that are home to an enticing array of shopping options, from long-time favorites to cool new boutiques.

Fleur carries fresh flowers and curated home goods, Pixie & The Boy stocks their shelves with fun and quirky gifts, Bric-a-Brac offers an extensive collection of records and toys, and Vintage Frills has all the best vintage finds.

For the crafty folks in your life, Firefly Fiber Arts Studio sells beautiful hand-dyed yarns and beginner how-to kits. And if you want a truly only-in-Chicago gift, Wolfbait & B-girls has tons of unique pottery, artwork, jewelry, clothing, and more all handmade by local artisans.