Chicago seems to have a new store to explore at every turn. Then, why not make this New Year the one where you explore all the small shopping options the city has to offer? With Clark Street posing as Andersonville’s Main Street, here are 9 great independent, boutiques in Andersonville to turn to the next time you want some shopping done. 

Transit Tees

5226 N Clark St, Chicago, IL 60640

Transit Tees is a great stop for all things “Chicago”. From t-shirts to glassware and coasters, if you’re looking to spruce up your space with the theme of the Windy City, Transit Tees is your go-to. Founded in 2001 by Tim Gillengarten, the goal of the shop is to take visuals from Chicago’s landscape and turn them into “art, accessories, home goods and more”. If you’re looking for something a little more personal, Transit Tees also offers custom t-shirt printing and has created original designs for Chicago staples like Morton Salt, Nori Sushi, and the West Town Chamber of Commerce. 


Andersonville Galleria

5247 N Clark St, Chicago, IL 60640 


Looking for tons of vendors in one place? Head to Andersonville Galleria! Here, local artists and sellers rent out spaces to sell their product. At Andersonville Galleria, you can find items created by photographers, ceramists, jewelry makers, painters, and illustrators, to name a few.

This is probably the best stop to spend an afternoon perusing the different booths and finding the next unique piece for your closet or space. Andersonville Galleria is open Monday through Saturday from 11am to 6pm, and Sundays from 11am to 7pm, so there’s an opportunity to visit every day. 


Milk Handmade

5137 N Clark St, Chicago, IL 60640

From cute clothes to home goods to jewelry, Milk Handmade is a one-stop shop for local vendors to sell their pieces. Within this Andersonville boutique, you’ll find everything both on trend and “staple” as you scan the racks at your leisure. At Milk Handmade, you’ll find items as simple as claw clips and more extravagant things like long coats and sweaters. Items here tend to be a bit on the pricey side, so if you’re looking to splurge on a great piece, Milk Handmade is definitely the best place to refresh your wardrobe in Chicago

Winifred Grace

5632 N Clark St, Chicago, IL 60660

Gorgeous, unique jewelry? Look no further. Winifred Grace has all the jewelry options you could want for any occasion. Necklaces, rings, earrings, you name it. One of the wonderful things that separates Winifred Grace from the rest is their permanent jewelry options. It’s as simple as booking an appointment online, paying the $30 deposit, and getting excited for a new piece of jewelry you definitely won’t lose! They also have a great selection of 14k gold chains, charms, and links for guests to choose from so you know your jewelry is going to be unique to you. 

Lilla Barn Clothing

5535 N Clark St, Chicago, IL 60640

Lilla Barn Clothing is full of bright colors, bold patterns, and sustainable clothes for both kids and adults. Stepping into their store is like walking into a world of happiness, and we can’t recommend it more. Lilla Barn features their own collections as well as other local vendors like January Moon and Land of Daughters. If you’re looking to get out of your typically neutral wardrobe into something more eye-catching, opt for a bright Gummiband, floral printed top, or Rainbow Road balloon pants. 

Sandbox Baby Boutique

5349 N Clark St, Chicago, IL 60640

For “fun and fresh” baby and children’s clothing, head to Sandbox Baby Boutique. Full of all the must have pieces for a growing kid, a trip to this boutique in Andersonville is going to leave you wanting to do a full closet refresh, for your kid! With neturals, playful colors, and seasonal favorites, shopping at Sandbox Baby Boutique is perfect for expecting parents, seasoned professionals, or those of us who want to buy some cute stuff for our nieces, nephews, and godchildren. The kids in your life are definitely going to be the best dressed at the playground once you discover the great options Sandbox has to offer! 

Cowboys & Astronauts

1478 W Summerdale Ave, Chicago, IL 60640

Co-founders and real-life partners Matthew Buccilla and Greg Lanier opened Cowboys & Astronauts with a singular mission in mind: a life well-lived. At this shop, not only will you find on trend apparel to freshen up your wardrobe, but the ideology that your new shirt, pants, lotion, or ceramic astronaut has the ability to be a part of the bigger picture of your life. Are you hosting friends in your home for the first time? Did you happen to meet a great person at the bar down the street, wearing an incredibly soft sherpa jacket? Cowboys & Astronauts focuses on the little things that become integral moments of our lives.

Mercantile M

5409 1/2 N Clark St, Chicago, IL 60640


If you’re an avid antiquer and haven’t been to Mercantile M, you’re seriously missing out. When you’re in the mood to scour a store for a “new to you” item, this should be a go-to stop. Filled to the brim with handcrafted art, vintage furniture, and clothing, you’re sure to find something that will light up your space. At Mercantile M, there are always new items coming in, so no trip is quite the same and you’ll always have something to look forward to. The store is open everyday from 11am to 7:30pm.

Women & Children First 

5233 N Clark St, Chicago, IL 60640

There’s nothing quite as soothing as an afternoon spent meandering the aisles of a bookstore. The scent of the pages, the quiet whispers between friends, and of course the exhilarating feeling of finding your next great read. Since 1979, Women & Children First has grown to become one of the largest feminist bookstores in the country, and is a great place if you’re looking to expand your knowledge on social matters or indulge in a novel that you’ve been dying to read. By carefully curating their selection of books, hosting author events, and working with local schools, Women & Children First prioritizes their role in the community and creates a safe space for everyone, no matter what.

Featured Image: Milk Handmade

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