Shopping » Chicago, IL

Shopping in Chicago, IL

Chicago is not only home to premium, high-end fashion, but the Windy City is also chock full of on-trend, individually owned boutiques featuring local designers and one-of-a-kind pieces. Here's your insiders guide to the best!
Max 5 stars
My Rating
Rollover to rate this

Comfort Me Boutique

Founded by a local mother and her two twenty-something daughters, Comfort Me is a welcome departure from the average boutique. What sets Comfort Me apart? The mom-and-daughter trio emphasize a low-key, relaxing shopping experience infused with their passion for fashion, appropriately summed up by their tagline, "... experience the true meaning of retail therapy". In addition to a warm and welcoming ambiance, Comfort Me offers a range of flattering on-trend pieces for every age set. Bonus: they feature local Chicago designers when possible. Whether you're searching for the perfect gift for your stylish BFF or something special for yourself, you'll find what you're looking for at this Lincoln Park gem. 


The sister to Lakeview's custom framing store, Foursided, Twosided initially opened because there wasn't enough room in Foursided for everything the owners wanted to sell. Described as a "curiosities emporium", Twosided is filled to the brim with custom and vintage trinkets,  gifts, stationary and even jewelry. This cozy boutique is nestled on the corner of the busy Clark and Wellington intersection in East Lakeview and is the place to go when looking for a unique knick knack.

As a bonus, there is a little hallway in the back that leads to the boutique next door - easy access for your next shopping adventure!

Lori's Shoes

Cleverly dubbed "The sole of Chicago", Lori's Shoes is one of the Windy City's most beloved shoe boutiques. You'll find all your favorites at this Lincoln Park landmark, from Steve Madden and Jessica Simpson to Charles David and Jeffrey Campbell. The owner, Lori Andre, takes twice yearly trips to Europe to remain on top of shoe trends. Don't miss the gigantic sale wall towards the back of the store where you can snatch up those coveted kicks for a fraction of the price.

M2 Boutique

If you need to find a gift for the girl who has everything, you'll find it here at M2 Boutique. This Southport neighborhood favorite, unassuming from the outside, is bursting with unique, gotta-have-it accessories. It should be noted there is limited clothing here, they specialize primarily in jewelry, handbags, wraps and the like. There is also a men's boutique, M4 Men, also owned by M2 and located conveniently next door.

Belmont Army

This gargantuan 28,000 square foot, 3-story shop offers everything under the sun, from vintage and new apparel and shoes to skateboarding equipment. Located in the high-energy area by the Belmont Brown and Red train line, Belmont Army is a hard-to-miss Chicago icon. Each floor is well stocked with wearable yet unique (and affordable) fashions. Their selection of sneakers is incredible, they have a superb selection of both retro and newer looks. Street parking is difficult in this busy neighborhood, your best bet is to take the train to the Belmont stop.