7 unique shops in Chicago Uptown


Chicago’s laid-back Uptown district is known for its trendy cafes, theatres, jazz lounges, bars and boutiques – including a number of stores you won’t find anywhere else.

(Photo: Woolly Mammoth)

Situated on Chicago’s Far North Side, the well-heeled residential area attracts large numbers of tourists and locals alike who come to enjoy its mix of commercial and cultural entertainment. Those keen to indulge in some retail therapy during their stay in Chicago will find themselves spoilt for choice Uptown. We’ve picked out 7 of the most unique shopping opportunities that the buzzing neighbourhood has to offer.

Woolly Mammoth 

If you’re keen to add a dash of whimsy to your home interior, then Woolly Mammoth will provide plenty of inspiration – and perhaps even something eye-catching to take back with you. Specialising in animal-themed ephemera, the store is brimming with unusual antiques, specimens and taxidermy spanning everything from the anatomical to the funerial to the circus. They also stock original art made in-house, charts, maps, tools and an assortment of items resurrected from the past.

1513 West Foster Avenue

Milk Handmade

(Photo: Jamie Kelter Davis)

A trailblazer in the world of sustainable fashion, Milk Handmade and its Chicago-born owner place a strong emphasis on supporting local artists and businesses. The women’s boutique houses a wide selection of womenswear, hand-crafted jewellery and accessories from independent designers who produce locally, ethically, and using environmentally friendly practices. Whether you’re seeking the softest most sensual tee, the perfect accessory to match your style, or a new number to spruce up your Saturday nights, there’s sure to be a one-of-a-kind item that catches the eye.

5137 North Clark Street

Andersonville Galleria

(Photo: Andersonville Galleria)

Chicago’s only year-round indoor art fest, featuring over 100 independent artists under one roof, Andersonville Galleria is a veritable city institution. Nestled in Chicago’s shopping heartland of Andersonville, a historic district that’s renowned for its Swedish roots, eye-catching architecture, and bustling retail scene, independent vendors pack the indoor market’s multiple floors each day selling apparel, gifts, gourmet foods, home furnishings, antiques, artisanal wares and artwork.

5247 North Clark Street

Malliway Bros. Spells, Charms, & Potions

(Photo: Malliway Bros. Spells, Charms, & Potions)

Opened in 2021 as the Harry Potter-led interest in all things witch and wizard-ey continued unabated, Malliway Bros. Spells, Charms, & Potions has built up a loyal fanbase of patrons who come to peruse the store’s huge assortment of magic-themed books, supplies and artefacts. Jade green walls, high ceilings and feather-trimmed lamps create an evocative Victorian backdrop for the store’s array of treasures. The shop also hosts frequent workshops and rituals focusing on various aspects of witchcraft

1407 West Morse Avenue

Doggy Glam Boutique

For many, having their own dog opens up a whole new world of sartorial opportunities. Launched by Mexican-born dog lover Rhonda Salazar, whose own four-legged friend Fendi inspired her to give other dog parents the option to find pieces that match their pet’s personality, Doggy Glam Boutique offers a wide choice of apparel and accessories that will inject a dash of chic into your daily walkies. From basic items including collars, leashes and harnesses, to more conspicuous pieces such as bandanas, sweaters, jackets, bows and ties, the uptown store is the go-to choice for Chicago’s more discerning dogs. There are also home accessories and customised options available.

 4414 North Clark Street

Squasht Boutique

(Photo: Squasht Boutique)

A designer-focused clothing and jewellery boutique nestled in the heart of uptown’s Ukrainian Village, Squasht enjoys a dedicated following of discerning fashionistas who flock here for its funky handmade dresses, reversible hats, tunics, headbands and plenty more. Independent and entirely women-owned, its founders pride themselves on designing and producing their own brand collection of women’s ready-to-wear clothing and accessories. As well as their home-produced items, they also stock pieces by dozens of other independent designers, both local and national.

2556 West Chicago Avenue


(Photo: Inkling)

Anyone seeking an artfully crafted gift or memento from their Chicago visit would do a lot worse than popping into Inkling – a warm, welcoming and somewhat quirky store close to the city’s lively Lake View East district. Inside, you’ll find a collection of charming curiosities and trinkets, as well as an extensive apothecary section. To spruce up your living room back home, there are also print racks and walls lined with colourful artwork. The shop also hosts regular craft meet-ups and trunk shows.

2917 1/2 North Broadway

By Paul Joseph