Let’s face it, Chicago is a boozy town. We can blame it on the frigid winters. On the bright side, there are tons of cool bars, jazz clubs, speakeasies, and wine lounges to choose from. You can travel back in time in a prohibition-era speakeasy, duck into a hidden bar inside a former bank vault, or step inside a jazz club steeped in the ‘30s and ‘40s. Whatever you choose, you can be sure it will be a great date atmosphere; upscale, energetic, and all around good vibes.

UPTOWN

THE GREEN MILL

This not-to-be-missed Uptown jazz club hosts the best in the industry and maybe even the ghost of Al Capone – the decor sure hasn't changed since his day – and that's what we love about this place. Keep in mind, it’s a jazz club with live music. We recommend coming here after you’ve had a chance to talk in a more quiet bar.
Address: 4802 North Broadway Street, Chicago, Illinois 60640
Website: http://greenmilljazz.com

FOUNTAINHEAD

If you're looking for a low-key bar featuring an impressive beer selection, seasonal rooftop garden, and organic pub eats, this is your spot. We love the atmosphere of this place and it gets even better when you head up to the rooftop on a warm, sunny Chicago summer day. Check out their events page for rooftop dinner parties, seasonal beer tastings, and more.
Address: 1970 W Montrose Ave, Chicago, IL 60613
Website: http://fountainheadchicago.com

HOPLEAF BAR

Hopleaf Bar is another atmospheric favorite due to its exposed brick crawling with green vines, candlelit tables on the patio, excellent beer selection, and unique menu (try the duck reuben!). The back patio would be our first date pick considering inside can become overly crowded and loud.
Address: 5148 N Clark St, Chicago, IL 60640
Website: http://www.hopleafbar.com

LAKEVIEW

BARCOCINA

The space, lighting, and overall atmosphere is excellent at this Mexican inspired restaurant right in the heart of Lakeview. Choose from the abundance in margarita varieties, categorized by "Sweet," "Spicy," and "Smoky". My personal favorite is the spicy El Fuego topped with jalapeno foam. The interior is beautiful – featuring rustic reclaimed wood, open-air garage doors, and sensual fireplaces. It feels like you're snuggled up in a mountain cabin all in the comfort of Chicago.
Address: 2901 N Sheffield Ave, Chicago, IL 60657
Website: http://www.barcocina.com

HEADQUARTERS BEERCADE

This is more than just a bar – it's an arcade. This is a great date for those preferring action versus sitting down over a cocktail. The expansiveness of the venue allows you to grab drinks at the bar, chat while people watching window-side, or meander through the maze of 40+ vintage arcade games. There's now a River North location for those who want to check it out and report back to us – but we're assuming it's not as cool as its Lakeview counterpart.
Address: 2833 N. Sheffield, Chicago, IL 60657
Website: http://hqbeercade.com/lakeview

DRYHOP

If your date is an ardent ale drinker, we highly recommend the Half Acre Tap Room. However, DryHop Brewers is a craft beer alternative that isn't quite so niche, mostly because of the small plate and full bar options. You can't go wrong by mixing innocuous small talk with a flight of in-house brews; that's the kind of disarming combination that guarantees a second date!
Address: 3155 N Broadway
Website: http://www.dryhopchicago.com

LINCOLN PARK

OYSTER BAH

This Lincoln Park oyster bar gets an A+. Grab a hightop next to the fully-retractable garage door and feel the breeze coming in off Halstead Street where people watching is readily available. Choose from a variety of beer, wine, and cocktails. Grab a few small plates, including oysters, crab bites and shrimp cocktail to share. If you're feeling a change in scenery, check out their downstairs space, the Low Tide Lounge.
Address: 1962 N. Halsted, Chicago 60614
Website: http://oysterbah.com

THE MONKEY'S PAW

I accidentally stumbled upon this place after a night of beer and wings at the Bird's Nest down the street – and what a contrast it was! The Monkey's Paw has a hint of sophistication with the coziness of an apres-ski lodge. The farm-to-table American fare consists of dishes such as Amish chicken, hearty soups, and artisanal cheeses. Start off by grabbing a drink at the spacious bar in front, then head to the back of the restaurant where you'll find two fireside leather chairs complete with your own library and boardgames.
Address: 2524 N Southport Ave, Chicago, IL 60614
Website: http://www.themonkeyspawchicago.com

THE BARRELHOUSE FLAT

The Barrelhouse Flat has a distinctive second floor that elicits an almost palpable sexual energy. If Humphrey Bogart were to go on a first date with Mae West, they'd definitely drink cognac-based cocktails at this joint. The Barrelhouse Flat has a more casual atmosphere than, say, The Violet Hour, but it's not the type of place to rock a salsa-stained Derrick Rose jersey. Source: Complex.com
Address: 2624 N Lincoln Ave, Chicago, IL 60614
Website: http://www.barrelhouseflat.com

OLD TOWN

THE VIG

The Vig Chicago is a 1950's themed sports parlor in the heart of Old Town with classic cocktails designed for the contemporary drinker. Go for the weekend "Liquid Brunch," or a nightcap from their "After Dinner" menu, or have your pick from The Book.
Address: 1527 N Wells St, Chicago, IL 60610
Website: http://www.thevigchicago.com

WICKER PARK

BORDEL

Bordel Cabaret & Cocktail Bar, located above Black Bull Tapas, strives to resemble a speakeasy-style bar. The bar's unmarked door inside Black Bull's foyer, the dim lighting and circular, red velvet-decked booths are meant to evoke a "European bohemian lifestyle." The decor and the menu are inspired by a time during Prohibition when American bartenders moved to Europe and developed classic cocktails such as the French 75 and Bloody Mary. There's also a stage at Bordel, where, depending on which night you visit, you might see a flamenco dancer clinking her castanets, a jazz pianist sitting down at the keys or a burlesque performer stepping into the spotlight. Source: RedEye Chicago
Address: 1721 W. Division St, Chicago, IL
Website: http://www.bordelchicago.com

THE VIOLET HOUR

Speakeasies have a sexy mystique about them, and that's exactly what you'll find at this Wicker Park cocktail lounge from Terry Alexander and crew. There's no sign except for a yellow lightbulb, and it's hard to find the entrance in the wood paneled exterior. Once inside, you'll spy a framed note requesting bargoers to refrain from cell phone use. But the decor is what's really striking: cornflower-blue walls, white crown molding, crystal chandeliers and gorgeous hardwood floors give the space an elegant ballroom-like feel. Extremely high-backed blue leather chairs clustered around tiny white nightstands illuminated by candlelight add an Alice-in-Wonderland air. Now let's get serious: The classic cocktails (gimlet, negroni, paloma) are superb. Bartenders make each with painstaking precision, using housemade simple syrups, bitters and twice-filtered ice cubes. But expect to wait a bit for each beverage as bartenders lovingly labor over their shakers – no doubt you'll find it worth it. Source: Metromix.com
Address: 1520 N Damen Ave, Chicago, IL 60622
Website: http://theviolethour.com

PUB ROYALE

We think Karan's 5-star Yelp review perfectly sums up what to expect at Pub Royale – "We rolled in on a Friday night, the place was packed. There was a 40 minute wait for a table. No space at the bar either so all 5 us huddle up over the drinks menu in a corner. The bartenders and waitstaff take notice of this and are extra accommodating. We get our first round of drinks and a spot under the menu board, order the Indian Hot Chicken. It arrives very promptly. It is finished very promptly. We get a table after 20-25 minutes and start ordering the hell out of that menu. Yes, we were a bit apprehensive about the Indian inspired food and how well it would be done but we were pleasantly surprised. Ordered the Salt Cod Samosas, Mussels & Naan, Lamb Dumplings, Gobi Manchurian. The turmeric aioli that comes with the fries was delicious, unique and very well balanced. The food appealed to an Indian palate but is definitely approachable and enjoyable for all. Cocktails were very well balanced and the beer list is nicely curated." Thank you Karan!
Address: 2049 W Division St, Chicago, IL 60622
Website: http://www.pubroyale.com

QUEEN MARY TAVERN

When my two good buddies arrived in town, I had my hopes set on exploring Wicker Park. After not being able to get a table at Pub Royale (see above), we headed down the street to the quaint Queen Mary Tavern where we spent the better portion of the night. This nautical-themed joint reminded me of a New York-style tavern that swallowed a submarine. They serve dishes such as clam chowder and oysters, yet the main focus is the extremely novel cocktails. Try the Daily Grog or the Hot Tea Punch. We sat at the communal tables at the end of the bar which supposedly makes you appear to be a bartender as I had multiple people ask me to whip up martinis. If playing bartender is not your thing, grab a couple bars stools or a side table for more privacy.
Address: 2125 W. Division St., Chicago, IL  60622  
Website: http://www.queenmarytavern.com

WEST LOOP

LONE WOLF

Lone Wolf may be best known for their selection of Three Floyds' beers, but the classic cocktails should not be left out. Sit at the small patio out front on a warm, sunny day, or head indoors to the full bar that is the centerpiece of the floor plan. For a more intimate conversation, try to score cozy corner seating. This is a great spot to grab a drink while you wait for your dinner reservations at Girl & The Goat or Au Cheval.
Address: 806 W Randolph St, Chicago, IL 60607
Website: http://www.lonewolftavern.com

BAR SIENA

When the owners first created Siena Tavern, much of the inspiration came from a quaint, casual and energetic bar and restaurant called La Taverna in Siena, Italy. That inspiration led to a more polished and expansive version better suited for River North. The neighborhood tavern is housed in a rustic, two-story space offering casual seating throughout the restaurant including the ground floor bar area and a dining room on the second floor, with a 25-foot-by-25- foot opening in the center, uniting the two levels. 
Address: 832 W Randolph St, Chicago, IL 60607
Website: http://www.barsiena.com

MAUDE'S LIQUOR BAR

This upscale joint is the kind of spot to show off your fancy threads. If you're dining, you can go for the $165 Shellfish Tower, or one of the slightly more affordable options under the "French" and "Almost French" sections. However, make sure to try one of their amazing cocktails while you're there.
Address: 840 W Randolph St, Chicago, IL 60607
Website: http://www.maudesliquorbar.com

GREEN STREET MEATS

If you're looking for a more energetic and quirky environment, Green Street Meats is your spot. The interior is filled with tin, concrete, and faded picnic tables that wrap around the centerpiece bar, while the exterior patio settles in underneath warm, dangling Italian lights. This counter-service joint can have a painfully long cue on weekend nights, but it's totally worth the wait. Order from the chalkboard menu of meats and seafood that are served fresh off the 12,000 pound smoker. The bar has 16 beers on tap plus a dozen more in cans. Personally, this is one of my favorite spots in the city. 
Address: 112 North Green Street, Chicago, IL 60606
Website: http://greenstreetmeats.com

RIVER NORTH

THREE DOTS AND A DASH

Three Dots And a Dash is a tiki-themed bar without the cheesy, bamboo-ridden tastelessness of a Jimmy Buffet concert parking lot. This joint has an endearing novelty that makes transitioning between conversation topics easy, which is an absolute luxury during a first date. 
Address: 435 N Clark St, Chicago, IL 60654
Website: http://threedotschicago.com

GT FISH & OYSTER

The bright, open, and clean interior features nautical decor such as sailing anchors and intertwined rope draped throughout the walls and ceilings. Sit at the bar situated in the middle of the restaurant where your bartender will explain the elaborate wine and champagne menu and variety of oysters. I recommend ordering two oysters from each region along with bubbly to complement the fishiness. Both are absolutely delicious! 
Address: 531 N Wells St, Chicago, IL 60654
Website: http://gtoyster.com

THE HAMPTON SOCIAL

This is another nautical-themed favorite in River North! The Hampton Social embodies everything an upscale Californian beach restaurant would entail – wide open bright, airy spaces allowing a pseudo sea-breeze to flow in from Chicago's streets, fresh seafood and beach-themed cocktails, and even a swinging hammock for lounging. Every Tuesday through Friday from 3 to 6pm enjoy half-priced pizza and bottles of rose.
Address: 353 W Hubbard St, Chicago, IL 60654
Website: http://thehamptonsocial.com

UNTITLED SUPPER CLUB

This River North bar takes after Prohibition-era speakeasies – low profile, low light, craft cocktails, champagne and secret entrances. It doubles as a supper club serving burgers and chops, and regularly features live music. For a "speakeasy" the space should feel anything but quaint, clocking in at 18,000 square feet with a hidden outdoor patio planned along Carroll Street. The restaurant space is divided in several different rooms, including a "library" with velvet booths and a separate lounge with a 30-foot bar. Oh, and we forgot to mention that Untitled serves the largest selection of American whiskey in the world, offering 4,750 varieties. Business casual dress attire is requested.
Address: 111 W Kinzie St, Chicago, IL 60654
Website: http://untitledsupperclub.com