Where to Shop with a Drink in Hand in Chicago

Updated October 29, 2018

Grabbing a coffee or cocktail to accompany your shopping expedition adds to the fun. However, enjoying some retail therapy can be stifled by signs that say 'no outside beverages,' especially if you're knee-deep in a bachelorette or much-needed friend time. Next time a shop clerk asks you to leave your beloved bevv outside, go with it and head to one of these Chicago Rex-approved retail destinations.

Pop-up shops are so hot right now. In fact, we agree that pop-up shops and traditional retail will become the new food trucks, which is why we'll get into that first.

Seasonal, Craft, and Pop-Up Markets

Shop Buzzed is a rotating pop up market with locations all over town. So far we've loved their selections of both vendors and hosts, including Revival Food Hall.

Farmers markets are a popular summer destination for Chicago residents, and many of them have beverages for purchase in addition to fresh produce and meats. The city has a helpful map of neighborhood farmers markets here. The Green City Market is the largest, operating a seasonal outdoor market May through October in Lincoln Park, June through October on Fulton Street, and indoors at the Peggy Notebaert Museum November through April.

The Argyle Night Market is a summer evening market with Asian delicacies, local vendors, crafts and live music in Argyle/Uptown. Sauced Market is also a boozy night market, popping up in locations such as Thalia Hall in Pilsen. Sauced works with local vendors, breweries, distilleries, and musicians to curate a fun night of shopping and grooving to music with a drink in hand.

Randolph Street Market is an indoor (and seasonal outdoor) market with over 100 vendors that opens one weekend per month. Browse vintage and designer goods, hand crafted trinkets and fancy foods while enjoying the drink of your choice. Randolph Market partners with local beverage crafters like CH Distillery to offer signature cocktails at the Market Bar - such as the Kringletini (featuring Bowtruss Coffee) during the holidays. Non-alcoholic liquid refreshments, wine and craft beer are also available.

The Chicago French Market sells delicious food and drink year-round, in addition to events, tastings, and pop-ups throughout the year. Pastoral is not only a great place to grab a glass of wine, but offers great food and gourmet gifts.

Join hundreds of local makers, bakers, chefs, artists, artisans, entrepreneurs and designers at Dose Pop-up Markets. 

The Plant hosts a year-round farmers market in Back of the Yards. The outdoor market operates on Saturdays from june through Labor Day, and the indoor market occurs the first Saturday of every month from October through May. The Plant is an eco-incubator that supports businesses using sustainable, community driven practices. Whiner Beer Company is one such business, and The Plant uses Whiner brewing grains to feed it fish. Fish waste is then used as food in the aquaponics farm. Whiner also hosts a winter market featuring hand made goods on the first Saturday of the month.

Related post: Holiday shopping paired with bevvs

Fashion and Apparel

Trunk Club’s Chicago Clubhouse is a great place for men and women to meet with a stylist while sipping on complimentary beer, wine, or cocktails from the Trunk Club bar (teetotalers can opt for coffee instead).

Boga is a menswear boutique where you can sip a cocktail and get outfitted with fashionable digs in the Loop.

ZipFit Denim is a jean boutique that takes the stress and effort out of finding the perfect pair of jeans. Even better, they will schedule a fitting for you and friends and let you bring in your own booze to help you slide right into the perfect pair!

Bucktown’s G Boutique hosts shopping parties for ladies looking to buy erotica and lingerie. Guests can reserve a private party and bring their own food and drink and shop, take a class, and celebrate girls night, showers, bachelorettes, or just your typical Monday! Thursday nights can be reserved for fundraising events.

Ad Hoc hosts end of season sale events with complimentary drinks. Embellish is another boutique that hosts events such as their annual sale, where guests sipped on bubbly and 10% of the day’s sales went to Friends of Filbert Playlot.


The Foxtrot market’s West Loop location on Lake Street is equipped with a Bowtruss Coffee bar so you can be energized while you peruse curated products to host the perfect party or night in.

Nearby PQM is more than a great place to wash down cured meats and sandwiches with local brews. The PQM culinary team hand selects nearly 200 items for their retail shop on Fulton Market, including artisanal olive oils, preserved tomatoes, spice blends, small production cheeses, seasonal produce, craft beer and old world wines - many of which would be difficult to find otherwise. Southport Grocery is another great neighborhood grocer and food/beverage purveyor in Southport/Lakeview.

Gene’s Sausage and Deli in Lincoln Square has a wide variety of European goods and handmade sausage, as well as a rooftop beer and wine garden.

Eataly is a terrific place to sample wine, relax with a beer, sip a coffee, or grab a bottle of pressed juice while shopping for Italian delicacies and imports year round. See a full list of classes and seasonal offerings on Eataly's Chicago site here.

Several Binny’s Beverage Depot locations have pop up demos of various wines and spirits to try on your next visit. Some locations such as Lincoln Park have an in-store tasting room, a destination to sip a craft beer, wine or a cocktail while you shop. Lush Wine and Spirits and House of Glunz are also great local options to drink while you shop...for drinks. If you need more than booze and specialty cheeses, nearby Whole Foods Lincoln Park and Marianos New City also have in-store craft beer, wine, and coffee to sip while you shop.

The Lincoln Park Whole Foods hosts craft beer events, wine tastings, and Drink and Draw nights the first Thursday of every month.


In Old Town, Plum Market is home to both an Intelligentsia Cafe and an in-store wine bar. Pete’s Fresh Market locations have the Lotus Café, a full service coffee bar at 118th & Ave O, Oakbrook Terrace, Madison & Western, Bridgeview, and Oak Park locations.

West Loop/River West Jewel Osco now has a craft beer bar, Kinzie on The Rocks.

Department Stores and Large Retailers

Large retailers like Nordstrom and Restoration Hardware are adding bars and restaurants to improve your shopping experience. 

3 arts club chicago

Amid Restoration Hardware’s ginormous 6 story shopping edifice lies the RH Chicago Three Arts Club Cafe (above). This Gold Coast coffee shop, restaurant and cocktail/wine bar brought you by Brendan Sodikoff leaves us wondering why you even need to leave the first floor atrium to go shopping...it’s all online anyway right? See the full menu here.

Nordstrom Michigan Avenue’s cafe and ebar have been long time staples in providing quality food and drink to supplement the shopping experience. However, the Mag Mile location has a new inHabitant. Following a remodel in 2015, the center of the second floor is now a cocktail lounge and wine bar - meet Habitant, another place to tie one on in the men's section. Fuel up before making that critical cologne decision. Find contact information and more details on the Nordstrom Michigan Avenue Site.

Block 37, an urban mall and home to Latinicity, is a great place to shop in The Loop. While there, be sure to treat yourself to cortaditos, hot chocolate, or a passion fruit pisco sour at Latinicity.

Many Target locations across the US have a Starbucks inside. Streeterville’s Target Express also has a wine bar for shoppers to enjoy.

Beverages are allowed, and in many cases encouraged, at these retail establishments:

Did we miss one? Send us your favorites!