All the Places in Chicago Where You Can Drink and Holiday Shop at the Same Time

Impulse buyers beware

December 10, 2019 10:49 am
rl grill chicago
At the RL Grill, you can enjoy a long, two-drink lunch in the middle of your shopping woes
RL Grill Chicago

Easiest way to take the edge off while finishing up all your last-minute holiday shopping? Doing so with a stiff drink at hand hand, which you can do at all nine of the brilliant, boozy retail experiences we’ve compiled below. Multitasking has never felt better.

Tapville Social at the Fashion Outlets of Chicago
5520 Fashion Outlets Way, Rosemont

Fill up on pour-your-own regional craft beer, wine and cider at this Rosemont hangout before scouring the strip for deals on everything from cashmere sweaters and premium leather boots to wedding registry-worthy cookware and nerd-approved electronics. Don’t forget that refill — Fashion Outlets is now the only shopping center in the Chicagoland area that allows customers to take their booze to go, so feel free to window-shop while you sip. 

1939 W North Ave.

Pick up some hard-to-find LPs for your favorite High Fidelity superfan at this polished Wicker Park record shop, then make your way to the bar and lose yourself to the sweet sounds of I Don’t Want No Shrubs, a puckery concoction loaded with Old Forester rye, rhubarb shrub, strawberry, lemon and salt. Just make sure to think twice before asking the unappreciated scholars behind the pine if they’ve got a copy of I Just Called to Say I Love You… 

Starbucks Reserve
646 N Michigan Ave.

Whiskey barrel-aged cold brew Old Fashioneds, creamy Espresso Martinis and a bevy of exclusive gear designed by Chicago artist Mac Blackout? Throw in some architecturally inspired specialty drinkware and this towering new coffee metropolis has all your holiday gifting bases covered. 

YETI Chicago
1572 N. Milwaukee Ave.

This Wicker Park newcomer has been keeping outdoorsy Chicagoans good and hydrated since last August, satiating their thirst not only with quality insulated coolers, tumblers, water bottles and koozies, but also with a state-of-the-art (and dog-friendly!) coffee shop and bar. Time it right and you might just catch your favorite local band taking over the store’s live music stage.

The Table at Crate
35 Oakbrook Center, Oak Brook

Chicago chef Bill Kim (Urban Belly) is behind this suburban all-day concept stashed inside the Oakbrook Mall’s bright and airy Crate & Barrel homeware shop. Saddle up to the eye-catching round bar and put those $30 Champagne flutes to the test with an effervescent Argentinian Extra Brut Rosé or mix it up with the aptly named Crate and Mary, a peppery blend of Tito’s Vodka and the store’s own signature Bloody Mary mix.

RL Restaurant
115 E Chicago Ave.

This country club-esque Chicago Avenue mainstay pairs upmarket cuisine with top shelf cocktails, fine wine and some of the best people watching in the city. Much like the brand itself, this 20-year-old collar-popping bar and grill has proven itself to be a true classic.

Habitant at Nordstrom
55 East Grand Ave.

Make a beeline for Nordstrom’s men’s section and you’ll stumble upon this sleek little tapas bar, fully stocked with enough high-end booze to fuel your pursuit of the perfect ribbed turtleneck. Wash down a plate of cilantro lime chicken tacos with a tangy and refreshing BTC (tequila, blood orange, agave, lime, soda) and think lazy summertime thoughts as the holiday shopping madness whirs around you.

2212 N. Clybourn Ave.

Leave your laptop at home, folks — this quirky Clybourn Avenue bookshop and bar has been a WiFi free zone since day one. Browse the shelves in search of the great American novel while sipping on one of 35(!) different beers or go big with a fittingly literary Hemingway Daiquiri. 

Asrai Garden West Loop
309 N Morgan St.

Gorgeous flowers, incredible jewelry, perfume, magazines, home goods, slick clothing and accessories curated by the absolute coolest people in Chicago? The only thing that could make that combo better is a delicious alcoholic beverage. Good thing this Wicker Park stalwart’s massive new West Loop location shares its home with City Mouse, the Ace Hotel’s one-stop shop for excellent bar food and even better craft cocktails, plus beer, wine and a couple of irresistible outdoor fire pits primed for post-splurging relaxation.


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