The Haute Seeker

The Best Neighborhoods to Shop Small this Holiday Season

Chicago is a hub of local businesses and entrepreneurship making it pretty easy to shop local 365 days of the year. This holiday season, celebrate your favorite local small businesses by shopping with them on Small Business Saturday. Discover new shops, great deals, and uplift your local community.

Check out our guide to shopping small this holiday season. Seek and find unique goods in cool neighborhoods as you shop and support local businesses.


Andersonville | Edgewater | Broadway

Patrons sampling wine during Andersonville Wine Walk // Image via Facebook

Andersonville is a neighborhood located on Chicago’s North Side. The community is known for its Swedish roots, historic architecture, and bustling Clark Street, the main corridor for food, shopping, and entertainment in the area. The neighborhood prides itself on equality and is home to one of Chicago’s largest LGBTQ+ populations. The neighborhood boasts over 325 businesses that have incredible backgrounds that make up this unique community.

Little Village

Little Village |  Marshall Square | South Lawndale

Shop and support the Little Village, this holiday season. The 26th Street retail district provides a familiar feeling of home for the Mexican-American community that resides in Chicago and welcomes visitors from all over to check out the vibrant neighborhood. Spend a day in this community sampling authentic Mexican food from various regions, spotting brightly adorned storefronts with Quinceañera dresses, and more inside this business district with 1,800 goods and services.

Rogers Park

Rogers Park | West Ridge

Shop small in the culturally rich neighborhood of Roger’s Park. The northernmost neighborhood offers an array of global cuisine, interesting shops, and an entertainment directory that is filled with art theater, music, and more. You’ll find something for everyone on your shopping list in the popular Chicago neighborhood. Learn more about Roger’s Park and its alliance of businesses by visiting their website here.

Albany Park

Albany Park | Mayfair | North Mayfair

Albany Park is a rich Northwest Side neighborhood made up of immigrants and an overall diverse population. From letterpress greeting cards and staple wine bars to award-winning taprooms and crave-worthy dessert shops, you can discover hundreds of small businesses in this community during the holiday season.


Pilsen | UIC

Cynthia Soto owner of Pocha Shop Artesanal in Pilsen // Image via ESDC Facebook

Pilsen dynamic neighborhood that is rich in history, culture, community, arts, food, and more. Pilsen was inhabited by German, Polish, Italian, and Czech immigrants. In the 1980s a large migration of Mexican and Mexican-Americans began to populate the neighborhood, which gave reign to the dominating Latix culture that is still popular in the neighborhood to this day. This holiday season, tour 18th Street and navigate your way through vintage shops and art galleries. Along the way, find grand murals in hidden alleyways and delicious cuisine in this popular neighborhood. Learn more about this popular business district here.

Wicker Park

Wicker Park | Bucktown

Wicker Park is by far one of Chicago’s coolest neighborhoods. The neighborhood has a wide variety of theaters, nightlife, restaurants, and boutique shops. Stroll through the popular corridors of Damen or Milwaukee and find an endless amount of things to eat, drink, and shop this holiday season. Find things to do, neighborhood business deals, and more here.

Logan Square

Milwaukee Ave | Logan Blvd | Armitage Ave

Logan Square is a hip destination for all of your holiday needs. The sorta quirky, the indie neighborhood is located in the North Central area of Chicago. Shop small businesses along the commercial strip of North Milwaukee and discover cool restaurants, low-key cocktail bars, and one-of-a-kind shops.

West Loop

West Loop | Fulton Market | Near West Side | Greektown

The posh neighborhood is home to Michelin star restaurants, glamourous nightlife, and premier shopping. The community is home to a mix of local boutiques and a selection of high-end chain shops. Seek and find a selection of local eats, drinks, and more in this popular neighborhood in Chicago.


North Kenwood | Oakland | Douglas | Grand Boulevard

Spend this holiday season shopping in the city’s ‘Black Metropolis’ also known as Bronzeville. Chicago’s Bronzeville community is known for its rich history and vast cultural contributions from civil rights activities, jazz legends, and Pultizer Prize-winning authors. Modern-day Bronzeville boasts a rich renaissance of its own with neighborhood shops, art, and restaurants that can only be found in the South Side neighborhood. For a full list of businesses check out Shop Local

Lincoln Square and Ravenswood

Foster Ave | Ashland Ave | Montrose Ave | Chicago River

Vin 312 // Image Lincoln Square Ravenswood Chamber of Commerce Facebook

Unwrap the magic of this Lincoln Square Ravenswood holiday season. The close-knit community gives you small-town vibes, within the city of Chicago. The community hosts annual events that draw visitors into historic European culture and German-American heritage. From independently-owned delicatessens and specialty shops to Black-owned restaurants and cute toy shops, you’ll be sure to discover something new as you shop small in this gem of a neighborhood. Find out how you can be rewarded for supporting neighborhood shops during the holiday season by visiting Lincoln

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