Chicago: How to Drink and Visit The Windy City Like a Local

Downtown Chicago’s lakefront-hugging Magnificent Mile, with its museums, landmarks, upscale shops, and restaurants, is a natural tourist attraction. But, like must urban cities, the Windy City has vibrant neighborhoods with nightlife and cultural destinations favored by its natives, such as the side-by-side ‘hoods Bucktown and Wicker Park.

Just outside downtown Chicago, on the city’s near north side, Wicker Park and Bucktown are popular districts for live music venues, bars, chef-driven restaurants, vintage shops, independently-owned boutiques, and art galleries — many housed within the Flat Iron Arts Building.  The historic three-story building is located at the intersection of Milwaukee, North, and Damen Avenues, also known as the Six Corners.

Across the street is the Northwest Tower, a 12-story art deco building, and the only skyscraper in Chicago constructed outside the downtown area.  Today, the tower houses a boutique hotel, The Robey Chicago, which offers its guests 180-degree views of the city skyline, including tree-lined streets and the steel girders of L train stops.


The Robey Chicago

The Robey Chicago Corner Suite

The interior design of this triangular hotel is a mix of vintage Old Chicago and contemporary industrial with dark woods and deep neutral colors.  The 69-roomed hotel offers complimentary Wi-Fi, and all rooms have bedside accessible electric outlets, plus, a Bluetooth-enabled sound system with personal media streaming right to the TV.  Other amenities include personal care from Le Labo, 400-thread count sheets and Robey’s signature soft denim robes.

Chicago Brunch Cafe Robey

The lobby level restaurant, Café Robey, serves brunch and dinner all seven days of the week. The rooftop cocktail lounge, Up & Up, has floor-to-ceiling windows and an outdoor terrace with stunning views. The Robey’s second-floor lounge serves as a workspace, and features comfy banquets and lounge seating.

TIP:  Ask for room # 704.  It’s a corner suite with panoramic views of the six street corners and full skyline.

2018 W North Ave., Chicago (Bucktown/Wicker Park),, @TheRobeyChicago

Happy Hour

The Violet Hour

The Violet Hour Bar

The Violet Hour serves pre-prohibition style cocktails in an elegant space with cornflower-blue walls, hardwood floors, and a singular light bulb designating its entrance.  Further in, you’ll find a marble bar that spans the length of the room, divided salons with high-backed blue leather chairs set around small white tables, and a house rule against cell phone use.  In addition to its James Beard Award-winning bar program, headed by Tobey Maloney, The Violet Hour also captures attention with a rotating mural on its façade.

The Violet Hour Absinthe Frappe Our Take on the adult snow cone

Monday through Thursday, from 6- 8PM, The Violet Hour hosts L’heure verte, -an absinthe happy hour with traditional absinthe drips and cocktails. Try the adult snow cone, Absinthe Frappe – La Muse Verte Absinthe is poured over crushed ice along with Orgeat Syrup and Lemon Oil.

1520 N. Damen Avenue, Chicago,, @TheVioletHour1


Up & Up at the Robey Chicago

the Rooftop Bar at the Robey Hotel Chicago

Stay local, and travel up to The Robey hotel’s 13th floor to the UP & UP rooftop cocktail lounge.  Relax on comfy sofas and watch the sunset through the floor-to-ceiling windows with cocktail in hand, or head out on the terrace with your nightcap for the stunning night sky views.

The Up & Up Game, Set, Matcha Cocktail

The UP & UP has an excellent list of cocktails to choose from, such as Game, Set, Matcha -Absolut Elyx, Yellow Chartreuse, St. Germaine, Lemon, Egg White and Matcha.

Hours:  6PM – 12AM, Monday – Thursday; 6PM – 1AM on Friday & 1PM – 1AM  on Saturday

2018 W North Ave., Chicago (The Robey Chicago rooftop on the 13th floor),

Venture out to the Fulton Market in Chicago’s trendy West Loop neighborhood.  Once the city’s meatpacking district, now the faded-brick warehouse buildings house multiple award-winning restaurants like The Girl & The Goat, Next, and The Publican as well as Google’s Midwest headquarters, which share the streets with delivery trucks and pallet jacks.

The Aviary at the Fulton Market

Aviary Awning Chicago Cocktails

The Aviary is a luxe cocktail lounge concept from James Beard award-winner and a recognized leader of molecular cuisine, Chef/Owner Grant Achatz’ (Alinea and Next).  The soft lit lounge is elegantly furnished with high-backed banquettes covered in tufted dove grey-colored leather and low round tables.  An open kitchen, separated from the lounge area with a rolled down metal grate, serves as the bar lab.

Chicago cocktails Aviary Jungle Bird

The Aviary offers several tasting menus pairing chef-designed bites and whimsical cocktails, such as Jungle Bird -Rum, Campari, Pineapple, and Rum spheres.

TIP:  Reservations are made via pre-paid booking:

Hours:  5:00 PM – 2AM, 7 nights a week.

955 W Fulton Market, Chicago (West Loop),, @TheAviary


Chicago Distilling Company

Distillery Room - Chicago Distilling Co

The Chicago Distilling Company is family owned and operated craft distillery in the nearby Logan Square neighborhood.  Take a tour from Noelle DiPrizio, or her husband Jay, of the 1700 square foot Distillery Room – viewable from a large picture window behind the bar of the front-end Tasting Room.  Here is where the magic happens, -from the bins of fresh grains to the distilling vats.

Chicago Taste Chicago Distilling Co - Vesper

Afterwards, back in the Tasting Room, sample classic cocktails mixed their barrel-finished spirits, like an Old Fashioned made with Chicago Distilling Co.’s Blind Tiger Bourbon, Bee’s Knees made from Chicago Distilling Co.’s Finn’s Gin, or the Vesper – Chicago Distilling Co.’s Ceres Vodka and Housemade Apéritif, then, garnished with a swath of Lemon Peel.

Tasting Room Hours: Thursday – Saturday, open at 5 PM

2359 N Milwaukee Ave, Chicago (Logan Square),, @chicagodistilling

Coffee & Donuts

Fairgrounds Coffee & Tea

Fairgrounds Coffee & Tea

Fairgrounds’ brew bar serves craft coffees and teas, brewed hot or cold, from around the US. Order by the cup, or try a flight of three 8oz. pours along with fresh-baked pastries or lunchtime items.  They also have eight seasonal taps including sparkling tea, cold brew, nitro, matcha, and kombucha.  Accessible at the service bar are taps for still water and sparkling water with cooper drinking cups.

1620 N. Milwaukee Ave. Chicago (Bucktown/Wicker Park),, @ourfairgrounds

Stan’s Donuts

Stan's Donuts Chicago Mix Bismark

Chicago bakery owner, Rich Labriola, partnered with Stan Berman, founder of Stan’s Donuts, to bring the California-style donut shop to the Midwest.  Enjoy all the standards as well as specialties like the Chicago Mix Bismark – a round doughnut with filled with cheese and caramel pastry cream, covered on top with caramel, and drizzled with Chicago Mix (caramel & cheddar) gourmet popcorn. Conveniently located next to the Blue Line’s Damen Ave. station, so you can grab one, or an assorted box, with a coffee to go before you hop on the elevated train, -or ‘L’, to the locals.

1560 N. Damen Avenue, Chicago (Wicker Park),, @stansdonutschicago


Café Robey

Chicago Brunch Cafe Robey

One of many things that makes Café Robey so special is that it serves brunch every day!  On the corner end of the Robey Chicago Hotel, the open kitchen restaurant has an Art Deco edge. In a nod to the city’s rich architectural history, the cafe is furnished with marble tables and chairs of ebony wood and burgundy leather.

Buttermilk Pancakes

For brunch, the menu offers all the favorites, – the Benedict, Avocado Toast, and Buttermilk Pancakes with Wisconsin maple syrup and whipped butter.  While, Sunday/Funday cocktails have Prohibition Era flair, such as Le Dame Blanc -Lavender infused Aquavit, Creme de Mure, Orange Shrub, and Lime

Hours:  Brunch, 10AM – 2PM and Dinner, 5 – 10PM (Friday & Saturday until 11PM)

1600 N Milwaukee Avenue, Chicago, (on lobby level at The Robey),, @caferobey

Publican Anker

Chicago Brunch Publican Anker Pork Rinds

Publican Anker, the sister to original Publican in Fulton Market, is an homage to the early 20th century saloons and breweries that once comprised Chicago’s Wicker Park neighborhood.  In an industrial-chic setting, the hip gastropub offers rustic fare, craft beer & signature cocktails.

Chicago Brunch Publican Anker Pub Mimosa

For brunch cocktails, Publican Anker add a Chicago drinking-style to classics, such as the refreshing Pub Mimosa –Wittekerke witbier (a Belgian spiced wheat beer), and fresh orange juice or the potent Verde Maria – Lunazul tequila blended with tomatillos, lime, and Verde Maria mix – homemade, avocado, cucumber and spicy pepper juice, and served with a Little Kings cream ale pony.

Chicago Brunch Publican Anker Pub Burger

Start with grilled oysters with yuzu koshu butter, or housemade pork rinds flavored with white cheddar and malt vinegar.  For mains, we recommend the scrumptious Ham & Eggs – fried eggs over English peas, bacon and grits, or the hardy Pub Burger, with American cheese and special sauce, served with garlic aioli drenched frites.

Brunch Hours: Saturday & Sunday: 10AM-3PM; All Day Menu available, everyday, 11:30AM to close.

1576 N Milwaukee Ave, Chicago (Wicker Park),, @PublicanAnker


Street Art

Vivian Maier Mural

Vivian Maier Mural Street Art

Renowned Brazilian street artist Eduardo Kobra has left his mark on Wicker Park, with a bright and engaging mural featuring late photographer Vivian Maier.  The mural is Located on the wall of a house on North Avenue just a few doors east of the local karaoke bar, Louie’s Pub.

1651 W. North Avenue, Chicago (Wicker Park)

Love Wall

Love Wall Chicago Art

The bold mural, by Matthew Hoffman, is painted in the Chicago based artist’s trademark cursive font, and is the most photographed wall in Chicago –from selfies to weddings.

1873 N. Damen Avenue, Chicago (Bucktown)


Chicago Sights Street Art Cowlileo

The life-size cow sculpture, made of cement and stucco, is peering into a telescope on the southwest corner of Damen Avenue and Churchill Street.  From Buffalo, NY artist Ken Aiken, this commissioned public art installation is modeled after Galileo, the famous Renaissance-era astronomer.

1808 N. Damen Avenue, Chicago (in front of Asha Salon, and across from The 606 in Bucktown)

The 606

The 606 Chicago

The 606 is a former elevated railroad line along the Bloomingdale Trail  that has been converted into an elevated greenway and trail. Bike, run or walk the 2.7-mile route, while enjoying art installations, tree top’s views of the neighborhood homes and streets, and the beautiful landscape design.

Head for the entrance at Churchill Field Playlot Park (1825 N. Damen Avenue).  However, there are 12 access points, approximately every quarter-mile, including near the Damen Avenue Station of the Blue Line.  Check out the interactive map on their website, or ask the friendly locals on how to get there.

1825 N. Damen Avenue (Churchill Field Playlot Park),, @The606Chicago

Local Cuisine

Chicago has an abundance of outstanding fine dining restaurants, yet your dining experience will be incomplete without feasting on some of its signature local dishes.  One being the hot Italian beef sandwich, and, of course, Chicago-style deep dish pizza.

Pan pizza was invented here, and no pizzeria chain does it better than Lou Malnati’s.  However, thin-crust pizza cut into squares, also known as a tavern cut, is more commonly served throughout the city.

You can find both local favorites in the Bucktown/Wicker Park area for carry out, or delivery via Grubhub.

Lou Malnati’s Pizzeria

Lou Malnati's Pizzeria Chicago Local Cuisine

Every Lou Malnati’s pizza is handmade from scratch using fresh ingredients, including their sweet and tangy sauce made from hand-selected California vine-ripened tomatoes.  The thickly laid fresh mozzarella cheese comes from the same small dairy that has supplied Lou Malnati’s for over 40 years, and the famous buttery crust is from a secret family recipe.

Order the Malnati Chicago Classic deep dish- made with Lou’s lean sausage and extra cheese on Buttercrust, with their House Salad and house-made Red Wine Vinaigrette.

1520 North Damen Avenue, Chicago (Bucktown/Wicker Park),, (773) 395-2400

Al’s Beef

Al's Beef Italian Beef Sandwich - Chicago local Cuisine

Al’s award-winning Chicago-style Italian beef is a hot sandwich made with 100% USDA beef, spices and signature gravy on French bread.  Order it dry, wet or dipped (entire sandwich is submerged in gravy), and add on homemade hot Giardiniera or sweet peppers, and fresh cut fries.

1300 N Milwaukee Avenue, Chicago (Wicker Park),, (773) 663-4800,

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