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Weekly Planner: Brunch News Edition

Brunch News Edition Lowcountry Adds Brunch Fasten those bibs, because brunch is served at Lowcountry. The South Loop outpost of the boil-in-a-bag seafood concept, which specializes in Cajun-style shellfish, has added weekend brunch to its popular portfolio. A slight departure from its usual eat-with-your-hands bag-centric menu, the brunch offerings span a spectrum of Southern comforts, from […]

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Jun 18, 2018 09:51 PM
Best Restaurants in Boystown

With June being Pride Month, there’s no better time of year to spend dining and drinking in Chicago’s Boystown neighborhood. The vibrant Lakeview area enclave is best known perhaps for its clubs, drag brunches and rainbow pylons, but the neighborhood is becoming a serious dining destination in its own right, thanks to restaurants like these: […]

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Jun 11, 2018 10:32 PM
Weekly Planner: Taco Joint’s Specials and ROOF on theWit’s Movie Series

Happy Hour at Punch Bowl Social Happy Hour at Punch Bowl Social Happy hour is the happiest of all when you’re surrounded by bowling alleys, bocce courts, karaoke rooms and dart boards. The West Loop’s brand new Punch Bowl Social, a behemoth dining and gaming complex out of Denver, has jumped on the happy hour bandwagon, […]

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Jun 05, 2018 06:53 PM

Best Bars for a Summer Night Cap in Chicago

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; photo by Francis Son


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. 

From the same folks who brought you GreenRiver comes Annex, a small and dimly lit oasis of high-end, seasonally inspired craft cocktails. The bar is located on the same 18th...

Adjacent to sister restaurant Roka Akor, Enolo Wine Bar offers a variety of chef-driven Italian fare to match a global selection of vino as well as craft beer and specialty...

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Ten years ago, a high-concept cocktail lounge setting up shop in a skyscraper would have never made the cut in Chicago. But GreenRiver is all about breaking the rules, and...

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Lone Wolf marks the latest resident on Randolph Street's Restaurant Row. Unlike anything else in the area, this no-frills bar harkens to Chicago's bygone tavern era, with rustic motif, a...

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