One of the quintessential parts of summer in Chicago involves lingering for hours on end on patios at restaurants and bars, pretty much until city noise ordinances require closing outdoor spaces at 11 PM or 12 AM. But that doesn’t mean the night’s over; rather, plenty of snazzy indoor bars afford nice, unique settings in which to wind down properly (or keep the party going) with a night cap. Herewith, your handy guide to late-night drinking in Chicago, from upbeat and musical to luxurious cocktail dens.
Annex at GreenRiver: When it comes to proper night caps, cocktails at Annex at GreenRiver are like the grand finale at the end of a drawn-out fireworks show. With some of the craftiest and most elegant cocktails in the city, the cozy 18th-floor hideaway is a surefire way to end your night with a bang, especially since they’re open until 1 AM Thursday-Saturday. With unexpected cocktail ingredients like galangal, jasmine and carrots, there’s plenty to pour over here. Try the fragrant Disc Jockey (pictured), a complex creation blending floral, tropical and spicy flavors together with London Dry gin, sherry, curaçao, coconut, lemon, galangal and curry leaf.
Enolo Wine Café: Not only does this comfy wine bar have a belated happy hour that runs from 9-10 PM, but it’s generally a great place to wind down with a glass or two of rosé, that essential summer elixir. It’s open until midnight Thursday-Saturday, and considering its River North location, utterly surrounded by patios and rooftops, it’s conveniently located for night capping needs.
Arbella: For something a little more upbeat, Arbella combines quality, inventive cocktails with dance party vibes. Open until 2 AM on Thursday and Friday and until 3 AM on Saturday, there’s plenty of time to take advantage of its expansive drink list of 30 cocktails, while grooving to different weekend DJ sets. One fun option is the Chicago Fire Extinguisher (pictured), a pungent, robust tipple made with Scotch, Luxardo Abano amaro and smoked angostura bitters. If you’re really feeling saucy, check out the “Not F*ckin’ Around” menu, which features adventurous and lavish drinks like the Third Cousin, with barrel-aged Cognac, coffee liqueur, amaro and bitters.
Eight Bar: If you’re weekending right, you’ll be liquored up by midnight, which means the interactive and playful cocktails at Eight Bar will make for an extra fun finale. With drinks inspired by and named for Magic 8 Ball responses, it’s a real crowd-pleaser for the late-night set. Options include the Signs Point to Yes (pictured), a tart and refreshing combo of Absolut Elyx vodka, lime, ginger beer, housemade Fernet and mint. If you’re feeling indecisive, though, the bar is happy to provide an actual Magic 8 Ball to decide for you. Eight Bar is open until 2 AM nightly.
Lone Wolf: Considering the sheer amount of restaurants in the neighborhood, the West Loop is an area that necessitates a good nightcap. And when it comes time for such things, Lone Wolf is the saving grace. The dark, cavernous tavern features an array of hearty digestif-type cocktails, wine and beer, all perfect for washing down dinner and winding down for the evening. For summer, try the Frozen Zamboni, a chilly blend of vodka, Campari and lemon, or the tropical Phosphorescent Dream, featuring pisco, passion fruit and lime. The Lone Wolf Single-barrel Old Fashioned is another good, bracing option, made with house-selected Four Roses single-barrel bourbon, Demerara sugar and bitters.