Cool Off with the Best Boozy Milkshakes in Chicago

Close up of woman with friends enjoying boozy milkshakes

Milkshakes are a great way to cool off during the dog days of summer. When made in cocktail form, however, milkshakes are taken to a whole new level. Enjoyed at one of the city’s famed rooftop bars or on a scenic patio along the city streets, boozy milkshakes are the perfect recipe to beat the summer heat. For the best of Chicago’s “adult milkshakes,” here are a few spots to explore:

The Pink Squirrel

Tucked away in Logan Square, The Pink Squirrel captures a distinctive vintage vibe. Part cocktail bar and part bowling alley, this retro hotspot is pure fun. The decor is eclectic and fun with Formica tables and kitschy knick-knacks scattered about. The cocktail menu has many throwback favorites that include the Sidecar, the Rob Roy and even a Harvey Wallbanger. The boozy milkshakes, however, are not to be missed with specialties such as The Pink Squirrel made with crème de cacao and vanilla ice cream or the minty fresh Grasshopper. 

Rudy’s Bar and Grill

A nod toward the classic pubs found throughout Chicago, Rudy’s Bar and Grill feels like the perfect neighborhood hangout spot. Filled with Chicago memorabilia and pictures of iconic Chicago scenes, Rudy’s Bar and Grill makes patrons feel right at home in its Loop location. While the pub-style menu is full of classic fare, the drinks menu is anything but standard. Served with Smirnoff Vodka, the milkshake martinis come in a variety of flavors including Pumpkin Spice, Double Chocolate and Dreamsicle.

Public House

Located in Near North Side, Public House is reminiscent of a true beer hall. This spacious venue has a little bit of everything, including indoor and outdoor seating and a large and festive bar area. Though known for their expansive beer selection, their Cake Shakes have become a customer favorite. These Instagram-worthy masterpieces are served with a slice of cake on top and come in flavors such as Chocolate Porter and Vanilla Stout.

Located in the heart of Chicago, 215 West Apartments offers easy access to everything Chicago has to offer, including great drinks like these. Please contact us for more information. You can also get a sneak peek with our online gallery.

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