Along North Avenue, historic buildings adorned with terra cotta design details and decorative cornices stand tall.
Walk along this thoroughfare, and you can get a sense of what the city must have felt like at the turn of the 20th century. In a way, it’s more of the same. The avenue is dotted with small businesses filling the streets with energy.
Chicago Plants is one of them, and it’s the first stop in this guide. Outside their store, a young couple maneuvers around the sidewalk. One has arms draped around a fig tree, and the other carefully balances two small cacti while scanning a ‘plant care card’ filled with watering and lighting instructions.
Inside, the store is filled with plants, rows upon rows. Behind the counter, shop owner Ryan Glynn advises a customer on fern care. It’s not just a shop; it’s a place to learn.
Founded during the pandemic, that time had many of us searching for a new path, Glynn among them. He left behind a career in accounting. He founded Chicago Plants with a simple aim: fill homes with greenery and keep them living. 
Come with questions. They’ll be able to guide you on what fits best in your space. If you want to go beyond just getting a few plants, the Chicago Plant’s team offers a full-service interiorscape consultation. 
The plant theme continues with a bite to eat at Handlebar. Walk a few doors down until you see this faded metal sign, which was once bright orange when originally hung two decades ago.
Continue inside for made-from-scratch vegan and vegetarian comfort food. 
It’s Saturday morning, and all the tables are filled. A few open stools can be found along the bar, where a backdrop of brewery posters and stickers fill the space with early-2000s Wicker Park punk vibes.
Vegan and vegetarian often get confused with bland, but that’s not the word to describe the food here. A brunch visit will have you debating between comfort food items like an airy biscuit smothered in seitan gravy sausage or a smoked gouda veggie chili mac.
Their menu makes you forget you’re not eating eat.
Continue on North Avenue to visit the last stop of this guide. Asrai Garden is famous in the floral world. Known for her free-spirited floral arrangements that mix native plants and rugged greenery, shop owner Elizabeth Cronin has run Asrai since 1999, and for her latest endeavor, you can find her as a judge on “Full Bloom,” HBO Max’s florist reality competition show.
Inside, floral arrangements are everywhere. Instead of the bright pastels typically seen in traditional flower shops, the walls here are painted black. A deer head looms over the counter, and the shelves brim with tarot cards, crystals, jewelry, and an eclectic assortment of items that pique Cronin’s interest.
As you linger, you won’t be alone. Other passersby enter the shop with a steady rhythm, intrigued by its ethereal and inviting allure. It feels a bit like an oddity shop — the type of place you visit when you don’t have anything specific in mind, but you go hoping to stumble upon that perfect thing you didn’t know you needed.
