by Jackie Rassner & Cecilia Karl
Put your money where your home is this holiday season and finish up your shopping right in your own neighborhood

With Christmas just days away, we don’t need to tell you that you’re running out of time to finish up your gift-giving list. This year, instead of paying through the roof for last-minute shipping online, we’re vowing to stay home and hit our neighborhood shops for our late-season shopping. The best part? With every purchase, you’ll funnel your hard-earned dollars right back into your own community, keeping the small businesses you love thriving throughout the season—and beyond. And with gifts this good, no one will ever know you waited until the last minute. That will be our little secret.


This north side neighborhood is known for its unique art, furniture, and antique stores. It’s well-suited to leisurely strolls, allowing you to pause now and then to pop into whatever shop grabs your interest.

A can’t-miss spot is Four Sided. Don’t be fooled by Four Sided’s humble billing, the shop offers much more than the custom framing it advertises. Stop here for great jewelry, vintage items, and sweet cards.

Or check out Andersonville Galleria, which features three floors of more than 90 independently owned booths, all boasting the wares of local Chicago artists. If you’re in the neighborhood, make the Galleria your one-stop shop for unique gifts ranging from one-of-a-kind clothing to scented candles and bath products.

For beautiful clothing, jewelry, and accessories handcrafted by independent designers, make a stop at Milk Handmade. Owner Hallie Borden keeps this beautiful boutique well-stocked with unique and affordable pieces fit for any woman on your list.
Got a vintage-lover in your life? Then visiting Scout—much beloved by celebrity designer Nate Berkus—is a must. Sure, there are big ticket items aplenty here, but you’ll also find more affordable quirky home accessories that are sure to delight.
Need to refuel while hitting the streets of Andersonville? Be sure to grab a cup of coffee at The Coffee Studio, a slice of pizza at Great Lakes (GQ Magazine’s #1 pick for pizza) or a craft beer at Hopleaf.

Lincoln Park

Step off the Brown Line at Armitage and behold an entire block of small shops just perfect for wiling away a Saturday afternoon. You could easily scratch off your entire holiday list on this block alone, and while you’re at it, scoop up a little something for yourself, too.

On the hunt for a small item for a gift exchange? Pop into Art Effect for unique jewelry, fancy soaps, picture frames, and other creative goodies. If you’re trying your best to not pick something up for yourself, we might recommend keeping your distance from the shops clothing boutique, which features a well-curated collection of trendy, unique, and classic pieces.

Don’t forget about shopping for the furry member in your family at the ‘Paw Firm’ of Barker and Meowsky. A one-of-a-kind pet boutique, this shop offers stylish products for the pets you love. Find pet apparel (send us photos, please!), cozy beds, collars, toys, carriers, and more.

For the little ones in your life, a trip to Rotofugi Designer Toy Store & Gallery is definitely in order. The husband and wife duo behind the shop stock the shelves with truly distinctive toys made both here in Chicago and all around the world. Find vinyl figurines, old-fashioned wooden toys, books & magazines, and more.

Wicker Park/Bucktown

It’s easy to find funky gifts in Wicker Park/Bucktown, visiting block after block of trendy fashion retailers. But at the corner of Division and Damen you can bet your bottom dollar you’ll find unique gifts for everyone from the baby in your life to your best friend.

Check out Building Block Toys for a fantastic selection of games, toys and stuffed animals. For a Chicago-centric gift, treat that train-loving kid in your life to a CTA bus or train for their tracks. We promise it will be just a touch cuter and cleaner than the real thing!

For your bookworms, pop by Myopic Books, where you’ll find four-stories of used reads in a well-stocked and organized shop. Be sure to check out the new arrivals cart for really good titles (think Rushdie, Didion, and Safran Foer). We promise there’s nothing about this place that feels like an academic’s discard pile.

Always a safe bet for a last minute gift, Mojo Spa features handmade skincare and bath products in the most delectable packaging (spoiler alert: the soaps look like decadently frosted cupcakes and cakes). While you’re here, browse the selection of on-trend jewelry and accessories—or pick up a gift card for a manicure.

When you’ve worked up an appetite, head up Milwaukee Avenue for a cheap Costa Rican feast at Irazu. Do yourself a favor—and allow us to live vicariously through you—by ordering the oatmeal shake. You won’t regret it.

Lincoln Square

Lincoln Square is a charming and serene setting for a laidback holiday shopping spree. With an independently owned shop just around every corner, you’ll be hard-pressed to go home empty-handed. Bonus: The gifts you find are guaranteed to be truly one-of-a-kind.

First stop? The Book Cellar. Treat the bibliophile in your life to a new book at this local favorite. The shop is stocked with staff picks, and the folks behind the counter are always willing to offer a recommendation, ensuring you find the perfect read for long winter nights. Need to chill out? Order a glass of wine from the shop’s café and cozy up on a couch surrounded by books until you’re ready to wander out again.

Another favorite haunt of ours is Sacred Art. This shop is like walking into Etsy. Push open the front door and you’re instantly greeted by the handmade creations of local artists. It’s a perfect stop for any Chicago-themed gifts, such as photography, t-shirts, or accessories.

Styled after an old-fashioned drugstore, Merz Apothecary is a safe bet for scoring indulgent and luxury bath and skincare products. From classic straight razors for the man in your life, to candles and aromatherapy, Merz has quite the wide selection to suit any of your gift-giving needs.

West Town

Cross over Halsted on Chicago into West Town to find gifts for your favorite epicurean or budding sommelier.

Start by treating yourself to a glass of wine and a cheese plate at Lush Wine and Spirits. After all, how can you take care of others if you haven’t first treated yourself well? When you’re ready, peruse the store or ask for a recommendation from the fantastic staff to find that bottle of wine, beer or spirit that makes a perfect hostess gift for your holiday parties. Don’t miss the $15 and under section for a budget-friendly bottle!

Another great hostess gift is a delicious pie from Hoosier Mama Pie Company. Hands down, the best piecrust in the city! For the baker on your list, pick up the bakery’s cookbook, chock full of deliciously decadent recipes straight from the pie shop’s kitchen.

If a touch of nature is what you’re after, step into Stems. There, florists can create a whimsical centerpiece to display at your holiday affair. The shop also stocks jewelry by local artists, air plants, and simple terrariums that would make a unique gift for anyone on your list.


With a booming and culturally rich arts district, this Chicago neighborhood just south of the Loop seems to buzz with creative energy. If you’re in the neighborhood, there’s no reason to travel out for holiday shopping. Find everything from vintage clothing and home décor to luxurious, handmade chocolates.

For a well-edited collection of vintage items for both the men and women on your list, make a visit to Market Supply Company. A one-stop shop for curated vintage clothing and accessories, Market Supply is sure to meet your gift-giving needs.

The Pilsen Outpost Pop-Up Shop invites you to swing by for handmade gifts inspired by the city of Chicago and crafted by local artists. Here, you’ll find handcrafted toys, silk screened t-shirts, limited edition art prints, and more.

For something sweet, push open the door to Chocolat Uzma Sharif. There, you’ll find handcrafted, artisanal, “east meets west” chocolates made by pastry chef and owner, Uzma. Beautifully and sustainably packaged, these sweets would make a no-brainer gift for in-laws or extended relatives this season.