5 Chicago Neighborhoods to Shop Local (and Live in!)

Exploring Chicago’s unique neighborhoods is so much fun! Each has its own character, just waiting to be discovered.  

If historic landmarks, public parks and architecture are the backbone of a neighborhood, local businesses are the heart. Whether you’re looking for a day of shopping somewhere new, or debating which neighborhood to call your home, browsing indie-retail is a great way to get a feel for an area. Maybe you’ll even make some new friends by chatting with shopkeepers who love sharing stories about their neighborhoods. 

Here’s a handy guide to my favorite local shopping strolls in Chicago, along with nearby apartments that would be ideal for anyone who loves living close to the coolest merchants in town.

#1: Lincoln Park

A view of a street along Chicago's Lincoln Park neighborhood
Lincoln Avenue is a great street to stroll to get to know Chicago’s Lincoln Park neighborhood.

The Best Spots to Shop in Lincoln Park

Lincoln Park is my favorite Chicago neighborhood to shop in. You can find a great mix of mom-and-pop shops as well as popular national brands. To get started, hit up these three areas in the neighborhood: 

  1. Armitage Avenue: From Halsted Street to Sheffield Avenue 
  2. Clark Street: From Belden Avenue to Wellington Avenue
  3. Halsted Avenue: From Armitage Avenue to Webster Avenue

Favorite Local Shops in Lincoln Park

Lincoln Park is a treasure trove of small businesses. Here are a few of my favorite spots to shop small: 

All She Wrote

  • 825 W. Armitage Avenue 
  • Shop All She Wrote for custom stationery, personalized gifts, home goods and more 

The Tie Bar

  • 918 W. Armitage Avenue
  • Ties and menswear accessories boutique

art effect

  • 934 W. Armitage Avenue 
  • Women ‘s fashion, jewelry and gifts 

Laudi Vidni

  • 1007 W. Armitage Avenue 
  • Shop Laundi Vidni‘s custom leather bags and goods made in Chicago

Alice and Wonder

  • 956 W. Webster Street
  • Trendy fashions for women + Chicago-inspired graphic t-shirts
The exterior of Alice and Wonder in Chicago's Lincoln Park neighborhood
Find pretty fun things at this women’s fashion boutique in Lincoln Park. Image: Alice and Wonder

Steve Quick Jeweler

  • 2471 N. Clark Street
  • Eclectic jewelry and custom-designed engagement rings 

The Best Apartments Near Lincoln Park Shopping

If you’re looking to rent an apartment in Lincoln Park, and being close to shopping is important to you, I have four suggestions: 

Elevate Lincoln Park

Located in the Wrightwood community in Lincoln Park, this modern mid-rise apartment building is close to shopping and has great outdoor spaces to relax in. 

Lincoln Common

This mega-complex is in the heart of Lincoln Park. Its two towers offer residents great views and modern finishes. 

Park View

Near everything Lincoln Park has to offer, Park View apartments has a great rooftop deck that overlooks the neighborhood’s namesake park. 

Eugenie Terrace

This luxury apartment building has a great bonus – it’s close to great shopping in Lincoln Park and Old Town too. 

An interior space at Lincoln Commons apartments in Lincoln Park
Modern chic studio apartment at Lincoln Common in Chicago’s Lincoln Park neighborhood.

#2: West Town

The Best Spots to Shop in West Town

Chicago’s West Town neighborhood – including Wicker Park – is bursting with the cutest shops. Take a spin around and hit up these four spots to find the best hot spots: 

  1. Milwaukee Avenue: From Western Avenue to Grand Avenue
  2. Division Street: From Milwaukee Ave. to Leavitt Street 
  3. Damen Avenue: From Armitage Avenue to Chicago Avenue
  4. Chicago Avenue: From Milwaukee Avenue to Western Avenue

Favorite Local Shops in West Town

From clothing boutiques to bookstores to plant shops, you’ll find everything you never knew you always needed. 

Steely Boutique

  • 1730 W. Division Street
  • Eclectic women’s clothing and accessories

Raw Edge

  • 1943 W. Division Street
  • Artisanal craft boutique, showcasing over 25 local artists


  • 1643 N. Damen Avenue
  • Independent women’s clothing boutique 

Quimby’s Bookstore

  • 1854 W. North Avenue
  • Indie bookstore specializing in offbeat titles, graphic novels, and various oddities

Aeslin Pup Hub

  • 1812 W. Chicago Avenue
  • 1448 W. Chicago Avenue 
  • 1904 N. Milwaukee Avenue
  • Local all-natural pet supply retail store plus dog daycare, boarding and grooming

Sprout Home

  • 745 N. Damen Avenue
  • Lush garden, floral, and home goods

Seek Vintage

  • 1433 W. Chicago Avenue
  • Vintage clothing, shoes, jewelry, home decor, kitchen wares, and curiosities 

April 7s Custom Framing

  • 766 N. Milwaukee Avenue
  • Custom framing services and unconventional ideas for art decor 
A display of art at a framing shop in Chicago's West Town
Creative custom frames display eclectic art at this West Town local shop. Image: April 7s

South Loop Loft

  • 685 N. Milwaukee Avenue
  • Exceptional collection of 20th century furniture and decor, including high-end imports from around the world

The Best Apartments Near West Town Shopping

Wicker Park isn’t just a fun neighborhood to shop in; it’s a favorite place for renters to call home, too. Check out these three apartments buildings in the middle of the action:   

Wicker Park Connection

Located right in the action on Division Street, this modern apartment building is close to fun shops in Wicker Park, plus some of my favorite restaurants. And even though I love shopping small, having a Target right next door is pretty amazing too! 

The Milwood

If you’re drawn to Wicker Park’s cool vintage shops, you’ve got to check out The Milwood apartments. The hipster vibe and historic building make this the coolest apartment building in West Town. 

606 Blue

This luxury apartment building is a popular one in West Town’s Bucktown. Close to shopping (including an Aldi grocery on the first floor!), residents absolutely rave about the staff and sense of community. 

A rooftop pool at Wicker Park Connection apartments in Chicago's West Town
Rooftop pool and sweeping skyline view at Wicker Park Connection apartments.

#3: West Loop

The Best Spots to Shop in the West Loop

The West Loop neighborhood might be best known for its restaurants, but the retail scene is booming too. There are three areas I like to hit up when the mood strikes to shop: 

  1. Fulton Market: From Halsted Street to Aberdeen Street
  2. Randolph Street: From Halsted Street to Racine Avenue
  3. Madison Street: From Morgan Street to Racine Avenue

Favorite Local Shops in West Loop

The shopping scene in West Loop is sophisticated and leans more upscale. If you’re looking to splurge, this is the neighborhood to shop. 

Morlen Sinoway Atelier


  • 171 N. Sangamon Street
  • High-end menswear and accessories

Alice and Ivory

  • 1101 W. Randolph Street
  • Bridal boutique featuring indie designers

Smitten Boutique

  • 1047 W. Madison Street
  • Invitations and gift shop 

Asrai Garden

  • 309 N. Morgan Street
  • Floral, plants, home decor and gifts 
The inside of Asrai Garden in Chicago's West Loop neighborhood
Beautiful planters, flowers, home goods, gifts at this West Loop botanical boutique. Image: Asrai Garden

Leaders 1354

  • 1152 W. Madison Street
  • Men’s street gear, sports apparel, athletic footwear and hats 

Cat and Mouse Games

  • 1112 W. Madison Street
  • Awesome assortment of games, puzzles, toys and children’s books

Open Books West Loop

  • 651 W. Lake Street
  • Beloved neighborhood used book store with over 50,000 books 

The Best Apartments Near West Loop Shopping

West Loop is one of Chicago’s most popular neighborhoods to rent an apartment in. Constant growth and development mean it’s home to some pretty incredible new apartment buildings

Union West

Just a block south of Restaurant Row, Union West Apartments are new and boast modern minimalist design that fits right into the neighborhood. 

Circa 922

Right across the street from Union West, you’ll find Circa 922. This mid-rise apartment building in West Loop has lofts and traditional floor plans. 

Porte Apartments

Community is at the heart of Porte Apartments. Spanning an entire city block, you’ll find more than 500 luxury apartments located just south of Fulton Market. 

Open concept living space inside Union West apartments in Chicago's West Loop
Chic lofty living at Union West apartments in Chicago’s West Loop neighborhood.

#4: Pilsen

The Best Spot to Shop in Pilsen

If you’ve never explored shops in the Pilsen neighborhood, grab your wallet and get going! You’ll want to head to 18th Street, from Halsted Street to Wood Street. 

Favorite Local Shops in Pilsen

Head to Pilsen for some of the coolest one-of-a-kind shops in Chicago:  


  • 1152 W 18th St.
  • Eco-boutique of sustainable home goods, clothing, textiles, jewelry, plants, apothecary

Knee Deep Vintage

Mestiza Shop

  • 1523 W 18th Street
  • Mexican gift shop with cultural arts and crafts, home decor, clothing, jewelry, showcases work by local artists
The interior of Mestiza Shop in Chicago's Pilsen neighborhood
Authentic Mexican folk art, decor and clothing found in Chicago’s Pilsen neighborhood. Image: Mestiza Shop

606 Records

  • 1808 S Allport Street
  • New and used vinyl records

The Best Apartments Near Pilsen Shopping

The Rosie

Opened in 2021, The Rosie apartments are located on Pilsen’s northern border. These luxury apartments are drop-dead beautiful! 

The Otis

Just blocks north of 18th street shopping, The Otis is located in the rehabbed Otis Elevator Company. This warehouse-style building is Cool (yes, with a capital C!). 

An interior space at The Rosie apartments in Chicago's Pilsen neighborhood
Cool corner unit overlooking Pilsen and other near west side Chicago neighborhoods at The Rosie apartments.

#5: Edgewater

The Best Spot to Shop in Edgewater

Looking for a place to shop and explore that’s off the beaten path? Treat yourself to an afternoon in Edgewater. You’ll want to pop over to Clark Street, from Foster Avenue to Victoria Street. 

Favorite Local Shops in Edgewater

Edgewater is such a fun community. Grab a bite to eat at Uvae, then wander in and out of my favorite small businesses: 

Gethsemane Garden Center & Wild Pansy Gift Shop

  • 5739 N. Clark St.
  • Garden, greenhouse, plants, flowers, gardening gifts, outdoor furniture 

Alamo Shoes

  • 5321 N Clark Street
  • Quality footwear, family-owned shop since 1973


  • 5634 N Clark Street
  • Household items, decor, vintage goods, eclectic art, furniture, gifts
A cute gift shop in Chicago's Edgewater neighborhood - Roost!
Hunt for one-of-a-kind gems to decorate your apartment at this upcycled and vintage home decor shop in Edgewater. Image: Roost

Cowboys and Astronauts

  • 1478 W Summerdale Avenue
  • Men’s clothing, lifestyle goods and gifts

The Best Apartments Near Edgewater Shopping

Did you know Chicago’s Edgewater neighborhood was originally a summer resort town? It still has that small-town vibe and apartments for rent that match its historic roots. 

The June

Close to shopping, restaurants and the lakefront, The June is a small apartment building with modern features and amenities. 

The Edison

Just a block from The June, The Edison has an old school feel that’s been totally modernized.

The Draper

This luxury building is just a couple blocks south of Edgewater, in Uptown, and offers up beautiful mid-century modern styled apartments. 

An interior at The Draper apartments in Chicago's Edgewater neighborhood
An old office building was redeveloped into retro-inspired modern lofts at The Draper apartments in Chicago’s Uptown neighborhood, right next to Edgewater.  

If you are shopping for a new apartment, and aren’t sure which neighborhood has the kind of stores, restaurants and recreation that you like best, reach out to HotSpot Rentals today. Our team of experts would love to help you find the perfect apartment in your favorite Chicago neighborhood.