#GrottoChicago | 12 Small Businesses in Chicago Where You’ll Find the Perfect Gift

Trying to find last-minute gifts? Check out our small business (Chicago-based) gift guide here.

Looking for some local connections to use in your Christmas shopping? Anyone can order anything from Amazon — share something unique with friends and family by purchasing from a small business in your neighborhood.

Here’s a starter pack for where to start your local shopping in Chicago. Wander into any of these stores and you’ll often find more than you were looking for. And you’ll leave feeling more connected to your neighborhood.

Logan Square

Fleur (2651 N. Milwaukee Ave)

Fleur began as a “floral bucket shop” and has grown into a beautiful shopping experience for both flowers and other gifts. You can pick up a gorgeous floral bouquet for your Christmas party host or find the perfect gift for the person in your life who names their house plants. As you wander through the lovely-smelling shop, you can also pick up any number of candles, natural skin and bath products, puzzles, or jewelry. And as a bonus, many of their products are partnered with social enterprises, like “Bright Endeavors” candles!

City Lit Books (2523 N. Kedzie Ave)

City Lit Books is the perfect stop for the book lovers in your life. It is a cozy, local bookstore full of handwritten recommendations in every section — from true crime, to cookbooks, to cultural studies. There is a particular attention to diversity across their shelves, including in the kids’ section in the back. The staff is very willing to help you find exactly what you need, and you can treat yourself to a little break and sit on the leather chairs by the fireplace in the back before you go.

Old Town

The Spice House (1512 N. Wells St)

The Spice House has been around since 1957, with locations in Chicago and Milwaukee (they have a strong game on Insta, too). This is a great place to find gifts for the amazing cooks in your life, as well as the aspiring chefs who could use a little gourmet help. You can buy any single spice you can imagine, as well as sets for the BBQ lover or Chai lover or curry lover … there are even “salt-free” spice sets for the relative you are trying to help be healthier! The staff can point you toward the sugar, the spice, and everything nice.

Judy Maxwell Home (1349 N. Wells St)

The Judy Maxwell Home is where you want to go to pick up a highly-sought-after “white elephant” gift for your extended family. With everything ranging from cute to absurd, you can pick up a classic game like Trouble, a farting giraffe stuffed animal, or mugs that look like an adorable marshmallow. There are also puzzles, notebooks, candles, and socks. And a whole section that is entirely pink! Needless to say, you should be able to find something for the “grab bag” gift exchange at work that you would be happy to end up with yourself.

Lincoln Park

Good Games Chicago (1145 W. Webster)

This shop is the destination for all the game players in your life. Walk into this store and you are greeted by floor-to-ceiling shelves full of games. Have a Settlers of Catan fan in your life? Here you can find every expansion pack and special version. Same goes for Ticket to Ride, Code Names, Monopoly, and pretty much everything else! Their games range from the classics to obscure strategy stories that take place in space, on the Western trail, or in a plant’s photosynthetic processes (for adults and kids!). Come in and tell the staff, “I know he likes this particular game,” and they will help you find a fun, original gift!

Dave’s Records (2604 N. Clark St)

At the door to Dave’s Records, visitors are greeted with a sign that reads, “NO CD’S — Never had ‘em! Never WILL!” Walk into this classic record shop and find people standing shoulder to shoulder flipping through bins upon bins upon bins of records. Here you can find old artists, modern artists, new records and used! There are both bins with a clear alphabetical organizational system and bins designed for you to hunt around to find the obscure gems. In these days where record players are making a strong comeback, this is the place to find the perfect gift for your musical loved one.


Wiggleyville (3337 N. Broadway)

Do you have family members who sign their Christmas cards from themselves and their dogs? Who hang stockings for both the human and canine members of their families? Then you cannot show up to Christmas without a gift for that pup, too — Wiggleyville is a great local pet shop to find the perfect toy, treat, or gift. Since 2005, they have been intentional about selling high quality and ecologically sustainable products for the dogs in your life!

Wrigleyville Sports (959 W. Addison)

30 years ago, the Carlstrom family opened up shop across the street from the Cubs’ ballpark. This is the fan store to go to for the Chicago sports lover in your life! While Cubs gear and memorabilia is primary, they have great Bears, Blackhawks, Bulls, Fire — and even White Sox gifts. You can find pretty much anything with a Chicago sports logo on it here: clothing, blankets, hats, ornaments, and much, much more. And if you need a gift for a “sports neutral” friend, you are in luck — there are plenty of gifts with the Chicago flag (or ketchup-less hotdogs) on them as well.


Chicago Fair Trade Holiday Pop Up Shop (5228 N. Clark Street)

This is Chicago Fair Trade’s 8th Annual holiday pop-up shop, and with more than 25 fair trade businesses in one place, you can find beautiful and unique gifts and support a living wage for artisans from all over the world. To highlight just a few of the many, many options, you might love the alpaca stuffed animals from Peru, table settings from India, or the wire baskets from South Africa. These one-of-a-kind gifts tell a story and connect you and the recipient with craftsmen around the globe. It is only open until December 24, so get there as soon as you can!

Andersonville Galleria (5247 N. Clark Street)

Walking through this three-story gallery is like shopping in an outdoor market with more than 100 vendor stalls, but with the benefit of being inside (given it is December in Chicago, after all). In adjacent stalls, you’ll find beautiful, classy gifts right next to the snarky and absurd. As you meander, you’ll find yourself amid photography, vases and pots, candles, paintings, stationary, and homemade jewelry. It seems likely you could find a gift for everyone on your list here, while supporting local vendors.


BottlesUp! (3164 N. Broadway)

You cannot go wrong with the gift of a good bottle of wine, and BottlesUp! is the place to go. In addition to wine, they also sell beer, spirits, sake, and hard seltzers and ciders. They have a unique color system to encourage you to try new things and regularly rotate their selections. BottlesUp! highlights smaller producers — especially minorities — and their knowledgeable and friendly staff is very excited to help you find exactly what you are looking for.

Foursided (2939 N. Broadway)

This custom frame shop has a couple of locations in Chicago where you can find vintage posters, beautiful prints, and many other unique gifts — in addition to custom framing. You can find and create custom gifts that highlight important qualities of your gift recipient — from their home state to the name and breed of their dog. They also carry bath and body gifts, candles and incense, and games and puzzles. And if you are looking for unique, Chicago-specific wall hangings, this is a very good place to find them.

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