Believe it or not, the holiday season is already upon us. Holiday trees and decorations are popping up around the city, friends and families are preparing for gatherings, and there’s a chill in the air. We’ll go from pumpkin spice to candy canes to New Year’s resolutions real quick. And before you know it, it’ll be 2025!

One thing we shouldn’t forget in the hustle and bustle of the season is shopping small when we can. Every year, the Saturday after Thanksgiving marks Small Business Saturday—a celebration of local shops ready to offer unique, thoughtful gifts for both in-store and online shoppers. Supporting these independent businesses not only boosts your immediate communities, but also adds a personal touch to your holiday gift-giving agenda.

Since the start of 2024, many small businesses have closed, while others continue to highlight the challenges of staying afloat. Luv Sick Plus for example, a curated vintage shop offering stylish clothing pieces in the sizes Large-4X (which is sadly a rare find in the world of sustainable fashion), has been especially transparent about these hardships recently—and they are not alone. Despite these hurdles, the overwhelming majority of small businesses continue to emphasize the importance of supporting local shops to strengthen our communities.

At Shall We Wine, we deeply appreciate all of you who have supported us and our vision over the years. This holiday season, we invite you to click below and explore our online gift shop for fun items like t-shirts, gift cards, and more.

However, while we welcome your support with open arms, we especially encourage you to shop small whenever possible in your communities, and not just for the holidays. We understand that in uncertain times it’s tough to prioritize local businesses, especially when price offerings often can’t compete with big-box stores. But think of the bigger picture and what type of impact you can make. Your grace and support mean the world to every small business owner, whether they operate a restaurant, retail storefront, or anything else.

With that said, just in time for Small Business Saturday on November 30th, here’s a quick list of wine and beverage shops around Chicago you can support this holiday season and beyond. While definitely not an exhaustive list, it’s a great starting point for shopping small. In no particular order:

57th Street Wines – Hyde Park
A neighborhood wine shop offering a curated selection of wines from around the world, with a special focus on small, independent producers and exceptional labels.

Bitter Pops – Lakeview

An LGBTQIA+-owned shop specializing in craft beer, wine, and artisanal spirits, this family-owned business hosts a myriad of community events. In addition to its selection of beverages, they also have a taproom and kitchen.

Maria’s Packaged Goods & Community Bar – Bridgeport

Maria’s is a hybrid bottle shop and bar known for its selection of wines, beers, and spirits, all served in a hip, laid-back atmosphere. The bottleshop offers a very small, curated selection upfront, while the bar, tucked behind the counter, adds to its charm.

Le Midi – Wicker Park
With a focus on small, artisanal, producers this is a delightful gem for wine lovers seeking a European-inspired experience right in Chicago. The intimate shop offers a well-curated selection of French wines, perfect for sipping or taking home. 

The Noble Grape –  West Town

A boutique wine shop, this neighborhood favorite also offers a solid selection of local craft beer and spirits. They champion the belief that wine should be both approachable and affordable.

Easy Does It – Logan Square
In the early 2010s, this spot used to be East Room, a hip bar and music venue that often hosted concerts, DJ sets, and dance parties. In recent years it has much of that same energy infused, but morphed into a wonderful natural wine hangout and shop.

Don’t Forget: With the gift-giving season in full swing, that means we’re also getting ready to make your shopping experience as fun and fabulous as the holidays themselves. Stay tuned for our annual Shall We Wine Holiday Gift Guide, coming very soon! Whether you’re treating yourself or hunting for the perfect present, we’ve got something for everyone on your list. Keep an eye out for our upcoming reminders—you won’t want to miss a single gift-worthy moment.