The Run Down

It’s not hard to love Andersonville. It’s a charming North Side pocket of eclecticness and eccentricity just waiting to be tapped. This neighborhood is worth a meandering walk down Clark Street punctuated with sweet treats, quirky thrift finds and a delicious cocktail. In this guide, find a serendipitous balance of all three at a gluten-free bakery, a locally beloved thrift store and an inviting cocktail bar.

1. Sweet Treats @ Defloured

2. Vintage Shopping @ Brown Elephant

3. Cocktails @ Nobody's Darling

1. Defloured

If you’ve got a hankering for a sweet treat every now and then, this is the place for you. The bakery runs the gamut of goods, offering cakes, pies, cookies, breads, bars scones and whoopie pies — all without gluten.

The endearing storefront on Balmoral Avenue, just steps from the bustling main drag, draws a crowd waiting outside. They’re gazing through the window, where the day’s treats are showcased.

You don’t go inside. Take your time assessing your options through the window and an employee will come out to take your order.  This day’s rotating menu featured a Nutella cookie sandwich, a classic sugar cookie, a cake pop, a slice of carrot cake slathered in cream cheese frosting.

Don’t let the gluten-free delineation scare you off, the treats and sweets are built for everyone — you’ll be hard-pressed to tell the difference.

If you’re looking to order something specific in advance, be sure to call and give 7-10 days heads up to ensure you get exactly what you’re hoping for.

2. Brown Elephant

On the tails of a sugar rush, take a walk around the corner and across the street to Brown Elephant, housed in the former Calo Theatre building, now designated as a Chicago landmark. The space is huge, packed with secondhand goods meant for you to dig through and make your own.

The front room is a collection of glassware and other household goods, while furniture and clothing make up the rest of the space — a towering dome chock full of character and history from the building’s days as a theater in the 20th century. The unique architecture and design provide a nice cherry on top to the already-enjoyable thrift experience.

If you’re an ambitious thrifter, leave yourself time to work your way through the maze of treasures. This thrift Mecca is not for the faint of heart.

That being said, be sure to take your time. As with the best thrift stores, this one can’t be adequately combed through with just a glance. If you rush through, you risk passing by the adorable glass figurines, the quippy mug collection or the scores of old books just waiting for another voracious reader to tear through them.

3. Nobody’s Darling

Now you’ve swapped a sugar rush for the dopamine hit that can only be explained by a thrift haul that will leave your friends asking, “You got all that for HOW much?!” There’s only one thing left to do: It’s time to celebrate with a cocktail.

Take your thrifted goodies and walk a few blocks west on Balmoral until you reach Nobody’s Darling, an inviting LGBTQ+ cocktail bar. A Black woman-owned establishment, the cozy space is known as a hub for queer women that offers an alternative to the dancey vibes of a business found a bit further south in Northalsted and geared toward gay men.

The entirety of Alice Walker’s poem “Be Nobody’s Darling” adorns a poster on the wall that welcomes you as you walk in, a welcome reminder of the bar’s namesake and generally good life advice.

Here’s one of the co-owners, Renauda Riddle, on the space she created.

The cocktail menu is nothing short of delightful. No matter your spirit of choice, the menu will take care of your needs. We recommend giving the “Kahlo Margarita” (described on the menu as “festive and spicy”) or the “Southside Lychee Martini” a try.

The drinks are refreshing and balanced, so those of you who are wary of too-sweet cocktails can relax. Enjoy the atmosphere, which varies depending on when you stop by. A weeknight is usually quieter but still lively, while a nice weekend in the summer might get you a different feel.