4 Chicago neighborhoods that make supporting Small Business Saturday easy

If you were to ask me what I would rather do than participate in Black Friday, I could easily come up with a list that would almost certainly include childbirth, wisdom tooth extraction sans novocaine and swimming naked in the Chicago river in February.

Black Friday is a combination of almost everything I imagine to be in my personal hell: enormous stressed-out masses of people competing for the same goods and resources, big-box stores, no customer service and a general prize for who can get the most amount of “stuff” while also getting the least amount of sleep. And don’t even get me started on how my iPhone auto-capitalizes Black Friday yet doesn’t auto-capitalize Thanksgiving. If that isn’t a sign of how our society is decaying into the void I don’t know what is. 

Look, I get the urge to get a good deal. There’s also potentially some argument to make in that shopping in person at least helps the local economy by keeping local people employed (as opposed to shopping online, where almost all the money you spend goes out of your local neighborhood/city/state and probably to a foreign-held entity that doesn’t pay taxes). However, I have to argue there’s an even better way.

Small Business Saturday is now in its seventh official year and it is something I cannot only get behind, it’s something I want to spread throughout the entire year and beyond.

You may ask: why shop Small Business Saturday? The answer is simple: the same reasons to shop small all year long!

1. All the money you spend goes directly back into the local economy, from the local taxes and the rent to the hourly wages for employees. You’re also simply just making the neighborhood a better place, which in turn makes Chicago as a whole a better place.

2. It keeps the local infrastructure unique. The reason Chicago draws in millions of tourists a year is because it doesn’t look or feel like a carbon copy of the rest of the country. Our streetscapes and local businesses are an enormous part of that.

3. You’ll find unique, quality gifts and goods curated by people who truly care about what they’re doing.

4. It’s so much more fun!

Small Business Saturday doesn’t have to be an all-or-nothing extravaganza, either. It gloriously also includes local coffee shops, delis, restaurants and sweets shops. Whether you find gifts for everyone on your list or only just a few, you are destined to have a great day, and that’s the beauty of the entire ordeal.

If you’re having trouble coming up with where to go to get out of the chain store rut, I’m here to help. These four Chicago neighborhoods are bursting with small businesses and make shopping on Small Business Saturday as pleasurable as Black Friday is soul-crushing.


Best ‘L’ stop: Berwyn Red Line

A walk north on Clark Street from Foster will amaze you with all the different types of shopping available. From the incredible children’s books section at Women and Children First and the independent art collaborative of Andersonville Galleria to any of the numerous antique stores, you are sure to find something for even the hardest person to shop for on your list. If you need a break from shopping, the Swedish History Museum is fantastic and has a large children’s play and learning area.

Where to take a break and get a treat: There are almost too many places that are all delectable in Andersonville to narrow this down, but First Slice Pie Café offers uniquely delicious treats and sweets.

Lincoln Square

Best ‘L’ stop: Western Brown Line

Prost! This traditionally German area deserves its picture in the dictionary next to “adorable neighborhood.” Be sure to stop in Timeless Toys to find those most special presents for the little ones, and Neighborly for some truly unique (and perhaps a little cheeky!) gifts as well. As if the shopping and plethora of food options aren’t enough to entice you there, Lincoln Square is having free activities such as their Ice Sculpture Spectacular and live Victorian caroling, culminating with the annual lighting of the Lincoln Square Christmas Tree at 5:30 p.m.

Where to take a break and get a treat: There are many places to pop in and grab a pastry, but Café Selmarie is a perpetual favorite right in the heart of Lincoln Square.

West Loop

Best ‘L’ stop: Morgan Pink/Green Lines

A walk down Madison will yield a plethora of shops that will be sure to check some lucky folks off your holiday lists. The Fig Tree is a surefire way to delight anyone, and the folks at Smitten Boutique will help you find the perfect gift for even the pickiest person on your list.

Where to take a break and get a treat: Little Goat Bakery and Warm Belly Bakery will make your day delicious.

Roscoe Village

Best ‘L’ stop: Paulina Brown Line

Take a trip on and around Lincoln Avenue around the Paulina Brown Line and you will never want to leave. The audiophiles in your family will appreciate the Chicago Music Exchange. The tots (and tots at heart) will adore Building Blocks toy store. You can please the fashionistas in your life at Bazar. And, if you’re really stuck for a gift (or need this yourself!), pop into Bitter Pops for some of the best selections of beers you can find anywhere, complete with a tasting room.

Where to take a break and get a treat: Dinkel’s Bakery. People speak only in two tones about Dinkel’s: hushed tones of pure reverence and shouting excitement at the thought of this bakery.

Whether you visit one or ten local businesses this Small Business Saturday, I do hope you’ll find it in your heart and wallet to participate. These neighborhoods and local shops are what make Chicago truly worth the winters.

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