It’s getting simmering hot in Chicago, and if you feel like you’re reaching your boiling point, you’re not alone. When we can’t bear the outdoors anymore, there’s nothing quite like enjoying a frosty cocktail to cool down from the summer heat. Whether you’re looking for frozen drinks in Chicago or delicious cold treats, here is a list of our favorites from Wicker Park. From Aperol popsicles at the Cabana Club, boozy vanilla milkshakes at Pink Squirrel, refreshing rosé ice cream from Jeni’s, and more, the neighborhood has plenty of treats to keep you cool and satisfy your sweet tooth.
1. Jeni’s Splendid Ice Cream
Transform your summer trips to the ice cream shop with a pint of booze-flavored ice cream from the renowned brand Jeni’s. Indulge in a range of their signature “Happy Hour” flavors, including Frosé—a revitalizing sorbet made with sangria, pear, strawberry, and watermelon, or their luxurious Middle West Whiskey & Pecans featuring butterscotch, honey, vanilla, and salted pecans.
2. Pink Squirrel Bar
Saunter over to Chicago’s Pink Squirrel Bar to revel in the nostalgic atmosphere reminiscent of a classic diner with a modern twist. Their signature, The Pink Squirrel milkshake, is an adult-approved rendition of the beloved childhood treat. It is made with crème de cacao, crème de noyaux, and vanilla ice cream, and topped with whipped cream.
3. Royal Palms Shuffleboard
For energizing frozen drinks in Chicago during late summer nights, try the Frozen Espresso Martini from Royal Palms. This vintage Florida-inspired shuffleboard bar is located in the heart of Wicker Park. The cocktail is made with Misguided Vodka, Riga Espresso, Kahlua, and cold brew. It’s the perfect refreshing drink for a game of shuffleboard or for relaxing on Royal Palm’s rooftop.
4. Ina Mae Tavern
At Ina Mae Tavern, a New Orleans-inspired restaurant, you can pick up a Sno Ball treat with a twist from their to-go pick-up window. Choose from a variety of flavors such as Bubble Gum, Cherry, Pineapple, Sour Grape, Green Apple, Strawberry, and more, and pair it with your choice of liquor. Mix and match your favorite flavor and liquor combinations and enjoy this frozen treat on Ina Mae’s sunny sidewalk patio.
5. Cabana Club
Located directly above the bustling corner of Damen, North, and Milwaukee Avenues is The Robey Hotel’s rooftop bar and pool, Cabana Club. They have a variety of refreshing frozen drinks in Chicago, such as the bright and bitter frozen Aperol Pop or the floral-inspired Made You Blush frozen cocktail with rose vodka, Aperol, elderflower, and lime. Not a fan of cocktails? You can also try their Frozen Shirley Temple, which is made with crisp lemon-lime soda, pomegranate, and orange flower water.
6. DSTRKT
Nestled in the lively Wicker Park, DSTRKT, a popular sports bar, proudly presents its range of elevated frozen cocktails known as “slurps.” From classics like frozen Strawberry Daiquiris and Pina Coladas to unique flavors like Mangonada with tequila, mango chamoy, and Passionfruit Hennessy, DSTRKT has a wide variety of frozen drink offerings to satisfy everyone.