The Vanilla Porter Cake Shake, Courtesy Public House Chicago
Have Your Cake, Drink It Too
Known for its wide selection of beers, River North's Public House is not afraid to take a good beer to the next level - meet the cake shake. Unlike the cake shake you may have ordered at Portillo's, the two Public House versions are comprised of ice cream, mixed in with craft beer as a base then topped with sprinkles and a slice of cake on top. The Chocolate Cake Stout Milkshake is a concoction of Boulder Shake Chocolate Porter and chocolate ice cream, topped with a large slice of chocolate cake. The Vanilla Porter Cake Shake (pictured above) is a blend of JP's Casper White Stout and vanilla ice cream, topped with a large slice of confetti buttercream cake.
Paris Club (also in River North) has a rum soaked sponge cake that will have your sponge Bob booze cake friends beside themselves (hard to choose a meme here). If that isn't impressive enough, head to Longman and Eagle for a boozy twinkie.
Spiked shakes don't always contain actual cake. Griddle 24 in River North has cocktail-themed boozy shakes like the Cinnashake, the Fireball's friendly after dinner cousin. 25 Degrees is another boozy milkshake option. Hamburger Mary's in Andersonville will serve up a boozy milkshake while you play charity bingo on Sunday and Monday nights. RJ Grunts will spike your milkshake after you enjoy some ice skating at the Lincoln Park zoo's seasonal ice rink. Burger Bar, Frances' Deli, DMK Burger Bar, Pick and Me Up in Wrigleyville are also boozy milkshake options.
Boozy Slushies on Tap
Whiskey Business, Wicker Park
When asked about the best rooftops in Wicker Park, Whiskey Business should always be in the conversation. And it's not just the boozy slushy options. Whiskey Business also hosts events like one of the few rooftop bar yoga classes when weather permits.
Parson's Chicken and Fish, Logan Square
Known for its original Negroni slushy, Parson's Chicken and Fish is a fun destination year-round. Tuck into Parson's for a burger and karaoke in the winter, and bask in summer's glory (and play some ping pong) when summer comes 'round.
The Boiler Room is an important honorable mention, as they serve whiskey ice cream cones.
Streeterville Social, Downtown/Streeterville
Atop the Loews Hotel in Streeterville is an adult playground with basket swing chairs, cornhole boards, and a plethora of boozy slushies. Although only a seasonal (read: sunny times) destination, Streeterville Social is an adult playground worth a visit.
The Hautest Chocolate in Town
Mindy's Hot Chocolate, Bucktown
Photo by @gracebonoma on Instagram
Mindy's Hot Chocolate is hands down the best place to savor hot chocolate concoctions whether plain or complex. Spiked hot chocolate is a staple here, with rotating choctails (did we just make that up?! Update: No.) you need to try.
Dove's Luncheonette serves tequila-infused hot chocolate with plenty of mouth-warming spices to keep you happy. In addition to the food, there are mezcal flights fit for foodies (who like drinkies) that can be sipped with house made sangrita. Here are some non-dessert drinkies we loved at Dove's:
Cindy's Rooftop at the Chicago Athletic Association, The Loop
Wow long title. Probably an ideal precursor to the complex set of ingredients that make up the boozy hot chocolate at Cindy's Rooftop. Cindy's has a dedicated hot chocolate menu that is only available during winter. Cindy's is a fabulous spot to take in city views before playing some serious games (bocce ball, shuffleboard, chess, and more) downstairs in the Game Room.
Photo: Cindy's Rooftop on Facebook
Homestead on the Roof, West Town
Above Roots Pizza, Homestead on the Roof is a great place to sip a boozy hot chocolate or spiked hot cider. Both of these hot totties are also available indoors during cold months.
The Bristol in Bucktown and Balena in Old Town also have spiked hot chocolates using Italian liqueur (it'll be a bit nutty).
Honorable mention: Cantina Laredo in River North has a spiked Mexican apple pie, which blends spicy cinnamon flavors with buttered brandy.
Bombo Bar, West Loop
Looking for hotter chocolates? Bombo Bar (and its neighbor Bar Siena) are well known for their s’mores and Funfetti Hot Chocolate.
Fireplace Inn in Old Town is a cozy place to take down a s'mores skillet, and is one of many great places in Chicago to have a drink by the fire.