Food & Drink

A Guide to Chicago's Best New Happy Hours

Published On 07/20/2015 Published On 07/20/2015
Bar Allegro cocktail in Chicago
Colin Beckett (edited)

Ever since last year’s glorious emancipation of the Illinois happy hour, Chicago has been flooded with cheap drink specials for the "thank god work’s over" crowd. How the hardened Midwestern drinkers of the city managed to survive without happy hour for over 25 years is beyond us, but now our pint glass overflows with specials, and it is all the sweeter. Here are a whole bunch of the best deals in Chicago.

AMK Kitchen Bar

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Venue Node ID

4170914

Venue Name

AMK Kitchen Bar

 

Neighborhood/Location

Bucktown

Description

When: Mon-Fri, 5-7pm
The deal: Half-price draft beers, $8 pizza

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Pork Shoppe

Venue node id

3037475
 

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Andersonville
When: Mon, 11am-2pm; Tues-Fri, 3-6pm
The deal: Rotating weekday specials including $3 pints on Tuesdays and $5 cocktails on Friday  
 

Izakaya Mita

Bucktown
When: Mon-Thurs, 5-7pm
The deal: $3 shots of Japanese whisky, $2.50 Kirin, and $5 select bottles of Baird
 

WhirlyBall

Bucktown
When: Sun-Wed, 4-7pm
The deal: Half-price beer cans and wine, $3.50 draft beer specials + half-price appetizers and sliders
 

The Lodge Tavern

Gold Coast
When: Mon-Fri, 4-7pm
The deal: Rotating drink specials throughout the week including $3 drafts on Fridays

Leigh Loftus/Woodie's Flat

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Venue Node ID

3554506

Venue Name

Woodie’s Flat

 

Neighborhood/Location

Old Town

Description

When: Mon-Fri, 5-7pm; Sun 8-10
The deal: Half-off Ketel One, Jack Daniels, Captain Morgan and Don Julio drinks, $2 beer of the month

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Mother's Too

Venue node id

4066512
 

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Gold Coast
When: Mon-Fri, 4-7pm
The deal: $6 domestic pitchers and $3 Green Line drafts
 

The Irish Oak

Lakeview
When: Mon-Fri, 7-9pm
The deal: Half-off Ketel One, Jack Daniel's, Captain Morgan, and Don Julio drinks; $2 beer of the month, half-off Bud Light drafts
 

Trader Todd's

Lakeview
When: Tues-Fri, 4:30-6:30pm
The deal: $1 Rolling Rock and $2 select apps
 

The Barrelhouse Flat

Lincoln Park
When: Sun-Thurs, 6-8pm
The deal: $6 Old Fashioneds, Tom Collinses, and daiquiris; $5 highballs; $4 Hadouken shots and $4 draft beers

Cantina Laredo Chicago

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Venue Node ID

4236956

Venue Name

Cantina Laredo

 

 

Neighborhood/Location

​River North

Description

When: Mon-Fri, 3:30-6:30pm
The deal: Half-off casaritas, house wine, draft and bottled beer

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River Shannon

Venue node id

4050171
 

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Lincoln Park
When: Mon-Fri, 5-8pm
The deal: $4 Jack Daniel's, Maestro Dobel, and Sailor Jerry Cocktails; $3 Southern Comfort cocktails
 

River Roast

River North
When: Mon-Thurs, 4:30-6:30pm
The deal: $5 draft beers and select small plates.
 

Reverie

River North
When: Mon-Thurs, 4-7pm
The deal: $20 specialty cocktail pitchers
 

Tallboy Taco

River North
When: Fri, 4-6pm
The deal: $5 margaritas

Silversmith Hotel Chicago Downtown Adamus
Silversmith Hotel Chicago Downtown

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Venue Node ID

4236976

Venue Name

Adamus Lounge at the Silversmith Hotel

 

 

Neighborhood/Location

​The Loop

Description

When: Mon-Fri, 5-8pm
The deal: $4 bottles/cans of beer, $5 glasses of wine, $6 rail cocktails, and $7 select apps

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Brownstone

Venue node id

3607044
 

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Lincoln Square
When: Mon-Thurs, 5-7pm; Fridays, 3:30-5:30pm; Sat-Sun, 3-5pm  
The deal: Half-price draft beers, wine, and mixed drinks
 

De Noche Mexicana

Logan Square
When: Mon-Thurs, 3-6pm
The deal: $4.50 margaritas
 

Emporium Logan Square

Logan Square
When: Mon, 5-9pm
The deal: $2 PBR, $2 well whiskey, and free pool
 

Carola's Hansa Clipper

Ravenswood
When: Mon-Fri, 5-7pm
The deal: $5 you-call-it well drinks

Cold Storage in Chicago
Cold Storage

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Venue Node ID

4171763

Venue Name

Cold Storage

 

Neighborhood/Location

West Loop

Description

When: Mon-Fri, 3-6pm
The deal: $3 draft beer, $1 oysters

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Gideon Welles

Venue node id

4066528
 

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Ravenswood
When: Mon-Fri, 3-5pm
The deal: $2 Miller Lite bottles, $3 Amstel and Heineken, half-price Illinois craft beers
 

Henry's

River North
When: Tues-Wed, 5-8pm; Thurs-Sat, 7-9pm; Sun, 5-8pm
The deal: Get any draft cocktail or beer, plus any slider, for the price of the current hour ($5 at 5pm, $6 at 6pm, etc.)
 

Municipal Bar + Dining Co.

River North
When: Mon-Fri, 4-7pm
The deal: $3 local drafts 
 

Oak + Char

River North
When: Every day, 4:30-6:30pm
The deal: $2 Miller High Life drafts, $4 craft beer drafts, $6 house cocktails, and $8 prime double cheeseburgers

drinks at The Stretch Bar & Grill in Chicago
The Stretch Bar & Grill

The Stretch

Lakeview
When: Fri, 6-10pm (non Cubs game days)
The deal: The $20 meal deal gets you domestic bottles and well drinks (max of three drinks per hour) and a cheeseburger with fries or appetizer of your choice; also $5 Jameson shots.
 

Pippin's Tavern

River North
When: Mon-Fri, 6:10-6:40pm
The deal: $2 well cocktails and domestic drafts
 

Streeter's Tavern

River North
When: Mon-Thurs, 4:30-7pm
The deal: Rotating drink specials throughout the week, including $3 domestic drafts on Tuesdays
 

Mahoney's Pub & Grille

River West
When: Mon-Fri, 5-8pm
The deal: $1 Bud/Bud Light and $1 Nacho Fries
 

Rogers Park Social

Rogers Park
When: Mon-Fri, 4-7pm
The deal: $5 Moscow Mules, $2 off any beer & shot combo, $5 glasses of select wines

Castaways in Chicago
Castaways

Castaways Bar & Grill

Lincoln Park
When: Tues, 4-8pm; Wed, 3-6pm; Thurs, 11am-11pm
The deal: Weekday specials include half-price margaritas and Lime-A-Ritas (Tues), $4 craft beers (Wed), and $22 buckets of domestic beer (Thurs).
 

Landshark Beer Garden at Navy Pier

Streeterville
When: Mon-Tues, 4-8pm; Thurs-Fri, 4-8pm
The deal: $3 domestic drafts, $5 Bud Light 'Ritas, $6 Tito’s vodka lemonade + $5 nachos
 

Mercat a la Planxa

South Loop
When: Mon-Fri, 4-6pm
The deal: Half-price sangria and cocktails
 

Heaven on Seven

The Loop
When: Thurs-Fri, 5:30-7:30pm
The deal: Mini hurricanes for $6 + $2 mini po-boys
 

Bascule Wine Bar & Bistro

University Village
When: Mon-Thurs, 3-6:30pm
The deal: $3 off select glasses of wine and half-price appetizers

Tavern on Little Fort in Chicago
Tavern on Little Fort

Tavern on Little Fort

North Center
When: Thurs-Fri, 4-7pm
The deal: $3 Miller Lite drafts and $3 Tito’s and lemonade
 

Carnivale

West Loop
When: Mon-Thurs, 5-7:30pm
The deal: Rotating specials, including half-priced pitchers of margaritas on Mondays
 

Momotaro

West Loop
When: Wed-Sun, 6-8pm
The deal: A Tiger beer and a shochu shot is included with the two-course ($19) or three-course ($23) tasting menu at the downstairs izakaya bar. 
 

The Ogden

West Loop
When: Mon-Fri, 1-4pm
The deal: Half-price drinks
 

Nellcôte

West Loop
When: Mon-Fri, 5-7pm; Sat-Sun, 11am-7pm
The deal: A beer and a 10in pizza for $10

The Franklin Room in Chicago
The Franklin Room

The Franklin Room

River North
When: Mon-Fri, 11:30am-2pm
The deal: $1 beers and select glasses of wine with $12 lunch purchase (limit two drinks)
 

TÊTE Charcuterie

West Loop
When: Tue-Thu, 5-6:30pm
The deal: $8 cocktails including the signature TÊTE A TÊTE “cherry phosphate” cocktail
 

MAK Restaurant

West Town
When: Mon-Fri, 5-7pm; Saturdays 5-9pm
The deal: $3 beers on weekdays, half-price wine and sake on Saturdays
 

Umami Burger

Wicker Park
When: Mon-Fri, 3-6pm
The deal: $5 draft beer, $6 wine, and $7 cocktails + $3 truffle fries and $4 sliders
 

Furious Spoon

Wicker Park
When: Wed, 11am-1am
The deal: $1 Hamm's to help get you through your hump day

The Hampton Social cocktail in Chicago
The Hampton Social

The Hampton Social

River North
When: Tues-Fri, 3-6pm
The deal: Half-price specialty cocktails and pizza
 

Commonwealth Tavern in Chicago
Commonwealth Tavern

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Commonwealth

Venue node id

4053101
 

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Roscoe Village
When: Fri, 3-7pm (half-price appetizers until 6pm)
The deal: $6 craft cocktails + half-price appetizers

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Venue Node ID

4237322

Venue Name

mEAT Chicago

 

 

Neighborhood/Location

Lakeview

Description

When: Mon-Thur, 5-7pm
The deal: Half-price specialty cocktails

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Venue Node ID

4237342

Venue Name

Wing Factory

 

 

Neighborhood/Location

Lincoln Park

Description

When: Every day, 6-7pm
The deal: $1 drafts, $1 mixed drinks

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Venue Node ID

4237357

Venue Name

Sedgwick’s

 

 

Neighborhood/Location

Lincoln Park

Description

When: Mon-Fri, 4-7pm
The deal: $3 Bud/Miller/Coors bottles, $3 well drinks, $3 glasses of wine, $5 Corona Bottles with a Casamigos Blanco shot

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Venue Node ID

3603653

Venue Name

Osteria Langhe

 

 

Neighborhood/Location

Logan Square

Description

When: Tue-Thur, 5:30-7pm
The deal: Half-price cocktails

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Cocktail at Bar Allegro in Chicago
Michelle Banovic

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Bar Allegro

Venue node id

4053220
 

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The Loop
When: Mon-Sun, 4-6pm
The deal: $5 red and white wine; $5 “bartender’s choice” signature cocktail

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Venue Node ID

3044059

Venue Name

Old Town Pour House

 

 

Neighborhood/Location

Old Town

Description

When: Mon-Fri, 5-7pm
The deal: $4 rotating happy hour beer, half-price beer bombs and wine

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Venue Node ID

4128267

Venue Name

Harry Caray's

 

 

Neighborhood/Location

River North

Description

When: Mon-Fri, 4-6pm
The deal: $3 Bud, Bud Light, and Miller Light, $5 select appetizers

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Venue Node ID

4237387

Venue Name

Nick’s Fishmarket Grill & Bar

 

 

Neighborhood/Location

River North

Description

When: Mon, Wed, Thur 2-7pm
The deal: $4 draft beers, $6 select wines by the glass, $7 cosmos, mules, mojitos; $1 oysters, $5 light bites

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Venue Node ID

4237410

Venue Name

Pi Gallery Bar

 

 

Neighborhood/Location

​River North

Description

When: Mon-Fri, 5-7pm
The deal: $3 draft beers, $4 vodka drinks, and half-off Scotch

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Venue Node ID

3952071

Venue Name

Division Ale House

 

 

Neighborhood/Location

​Wicker Park

Description

When: Mon-Thur, 6-9pm
The deal: $4 pints and well drinks, $5 glasses of wines

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The Betty in Chicago
The Betty

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The Betty

Venue node id

3941441
 

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West Loop
When: Mon-Fri, 4-630pm 
The deal: Half-price draft beers, wine, and mixed drinks

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Venue Node ID

4237419

Venue Name

Waterhouse

 

 

Neighborhood/Location

Roscoe Village

Description

When: Mon-Thur, 5-7pm
The deal: Half-price specialty cocktails, $2 Bud Light drafts

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Venue Node ID

4237432

Venue Name

Congress Plaza Hotel

 

 

Neighborhood/Location

​The Loop

Description

When: Mon-Fri, 3-6pm
The deal: $4 cans of Miller Lite, Smith & Forge, REDD's Apple Ale, and Miller High Life

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Venue Node ID

4237440

Venue Name

III Fork Steakhouse

 

 

Neighborhood/Location

The ​Loop

Description

When: Mon-Fri, 4-6pm
The deal: Half-price beer and cocktails, $1 oysters

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Venue Node ID

4237449

Venue Name

Ph.D Pub

 

 

Neighborhood/Location

University Village

Description

When: Mon-Thur, 5-7pm
The deal: Half-price well drinks, $6 boilermakers

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Venue Node ID

4050239

Venue Name

The Boundary

 

 

Neighborhood/Location

Wicker Park

Description

When: Mon-Fri, 5-7pm
The deal: $4 rotating happy hour beer, $5 Tito's cocktails, half-price apps, and wine

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Matt Spina is a writer living in Chicago who should not be trusted with $2 drafts and especially 30 cent wings. Follow his occasional thoughts @MR_spina.

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1. AMK Kitchen Bar 1954 W Armitage Ave, Chicago, IL 60622 (Bucktown)

Comfort food goes chic at this creative, casual diner in Bucktown. Their extensive menu promises plenty of options for all, but we recommend their "ultimate" grilled cheese, which lives up to its name with five cheeses, bacon, and tomato jam. Check out their happy hour deals, half price draft beers and $8 pizza, Monday through Friday, 5-7pm.

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2. Pork Shoppe 5721 N Clark St, Chicago, IL 60660 (Andersonville)

This 38-seat outlet of porcine goodness is decked out with mounted farm tools and pig diagrams in a barn-like space. Smoked baby back ribs, pulled pig & fowl, Texas-style brisket, and sliced steak dominate the menu alongside a choice of three different sauces: molasses-based Sweet & Sticky, vinegar-y Tart & Tangy, and Wicked Spicy. Atop a fluffy brioche bun, meaty, fatty bacon that's been cured for ten days a smoked for 12 hours meets pastrami on what is undoubtedly one of the best sandwiches in the city.

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3. Izakaya Mita 1960 N Damen Ave, Chicago, IL 60647 (Bucktown)

An izakaya is a Japanese style drinking establishment, notable for its informal setting and popularity for after-work drinking. Izakaya Mita calls itself an authentic Japanese izakaya establishment, and serves small plates, grilled dishes, sashimi, noodles, and tempura alongside sake and cocktails.

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4. WhirlyBall Bucktown 1825 W Webster Ave, Chicago, IL 60614 (Bucktown)

Whirlyball combines lacrosse, basketball, and a bumper car arena -- and it's also super fun. This gigantic Whirly complex in Bucktown is complete with a 32-strong beer list, Buffalo chicken BLTs, bowling, laser tag, and 60 flat screens.

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5. Lodge Tavern 21 W Division St, Chicago, IL 60610 (Gold Coast)

Over fifty years in the Chicago-nightlife scene have left the Lodge as an icon -- a simple bar that hasn't changed much since they opened their doors in 1957.

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6. Woodie's Flat 1535 N Wells St, Chicago, IL 60610 (Near North Side)

At Woodie's Flat you can get your favorite American beer and a delicious wood-fired burger to match. Look for drink specials and great food at this Near North Side establishment.

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7. Mother's Too 14 W Division St, Chicago, IL 60610 (Gold Coast)

This bar takes its inspiration from the saloon-style bars of Nashville. They bring in a rotation of live acoustic acts every night from Wednesday to Sunday -- and there's no cover.

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8. The Irish Oak 3511 N Clark St, Chicago, IL 60657 (Lakeview)

The Irish Oak is a serious, almost literally imported, Irish pub. With two bars, a Signature Whiskey Still Room, and a menu featuring fish-and-chips, Irish stew, and Corned Beef, there's no denying the style of this bar or the fact that you'll probably love it.

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9. Trader Todd's 3216 N Sheffield Ave, Chicago, IL 60657 (Lakeview)

At Trader Todd's you can sing karaoke, drink in a beer garden setting and make a fool of yourself all in one place. Grab a mic and a tiki-tropical drink and start singing.

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10. Barrelhouse Flat 2624 N Lincoln Ave, Chicago, IL 60614 (Lincoln Park)

This two-floor throwback cocktail bar in Lincoln Park churns out classic tipples like Sazeracs, Old Fashioneds and Manhattans alongside lesser-known drinks like the Jimmie Roosevelt, a blend of cognac, green chartreuse and Champagne. Choose from 60+ varieties of shaken or stirred drinks.

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11. Cantina Laredo 508 N State St, Chicago, IL 60654 (River North)

CL serves authentic Mexican food with a modern twist. Menu items include grilled fish, chicken or steak topped with one of a kind signature sauces like chipotle-wine and Portobello mushroom or sautéed artichoke heart and roasted red bell pepper. It’s an upscale spot, so be ready to dine like a king (there are worse things, right?). Stop in Monday through Friday, 3:30-6:30pm for a bangin' happy hour: half-off casaritas, house wine, draft and bottled beer.

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12. River Shannon 425 W Armitage Ave, Chicago, IL 60614 (Lincoln Park)

This Irish pub has allegedly been open in Lincoln Park since around 1946. They boast a menu with plenty of beer and Irish whiskeys, and have a giant Jenga set in the back.

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13. River Roast 315 N LaSalle St, Chicago, IL 60654 (River North)

On the north bank of the Chicago River is River Roast, an upscale tavern that combines traditional British roasts with new American ingredients. The menu revolves around roasted proteins -- fish, beef, chicken, pork -- that are carved table-side for two. There are also a variety of small plates and vegetables to share. The large space includes two bars and an expansive riverside patio.

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14. reverie 414 N Orleans St, Chicago, IL 60654 (River North)

Sports games and high quality food merge at this River North Asian Fusion lounge from Rodelio Aglibot of Yum Cha. The menu features a number of shared plates and inventive rolls like the "I Have a Daydream," and the drink menu offers up numerous specialty cocktails.

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15. Tallboy Taco 325 West Huron, Chicago, IL 60654 (River North)

Located in River North, Tallboy Taco is a cozy, café light-strewn taqueria set up inside Nacional 27 that's offering counter-service lunch, full-service dinner, eight killer taco varieties (including a 12-hour smoked brisket taco, a shredded adobo chicken taco, and a meatless beer-battered avocado taco), and a tallboy selection that runs more than a dozen brews deep.

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16. Adamus 10 S Wabash Ave, Chicago, IL 60603 (Loop)

Adamus is a lively restaurant and lounge inside The Silversmith Hotel. Experienced mixologists serve specialty cocktails that you won’t find anywhere else, and the food menu features contemporary American cuisine that uses fresh, local ingredients. The sleek decor presents a perfect backdrop to sip aperitifs, and the contemporary, illuminated bar takes center stage for a mingling crowd. Stop in Monday through Friday for enticing happy hour deals.

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17. Brownstone Tavern & Grill 3937 N Lincoln Ave, Chicago, IL 60613 (North Center)

Bronze fixtures and stained glass might remind you of the idea of a classic brownstone, but we doubt that's what you're going to focus on in this saloon. Your focus will likely be caught by the 16 beers on tap, 40 more in bottles or the slightly upscale American contemporary menu. If that sounds like a bunch of buzz words, think seared ahi tuna, soft pretzels, and sandwiches named after Chicago highlights like "lakeshore Drive".

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18. D'Noche 2710 N Milwaukee Ave, Chicago, IL 60647 (Logan Square)

This Latin spot in Logan Square serves up Cuban, Mexican and South American original recipes and plate presentations in a trendy, urban space. The atmosphere feels modern, definitely not hole-in-the-wall. It’s good for dates, romantic or casual dining, and even large groups. Happy hour is Monday through Thursday, from 3 to 6pm, with a $4.50 margarita deal. One of the most popular is “Oaxaquita" made with mezcal and chili powder with a chili and salt rim (different for sure, but perfect for the drink). Start with a plate of croquetas— the aioli like sauce is delicious and you’ll want to pour the rest of it onto your entree.

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19. Emporium Logan Square 2363 N Milwaukee, Chicago, IL 60647 (Logan Square)

Emporium’s added a new location in Logan Square that's even bigger than the original and full of video games, an indoor food truck, plus vintage pinball, bubble hockey, and pool.

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20. Carola's Hansa Clipper 4659 N Lincoln Ave, Chicago, IL 60625 (Ravenswood)

This neighborhood bar specializes in German beers and liqueurs, and has some great cocktails as well.

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21. Cold Storage 1000 W. Fulton Market, Chicago, 60607 (Near North Side)

This casual but refined seafood concept inside Swift & Sons specializes in shellfish towers, seafood items both large and small, fish sandwiches, and best of all, ice cream sundaes. The 60-seat space is equally chic but more laid-back than its steakhouse sibling.

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22. Gideon Welles 4500 N Lincoln Ave, Chicago, IL 60625 (Ravenswood)

Gideon Welles, the man, was a 19th-century journalist and politician who served as secretary of the U.S. Navy from 1861-1869, but as serious as that sounds, you'll find wacky prints of him on the exposed-brick walls at Gideon Welles, the pub. This friendly Ravenswood spot is cooking up everything from pulled pork nachos to a beet & goat cheese salad to the Old Neptune Burger, topped with triple cream brie, tangy tomato chutney, and a giant onion ring. There's also an extensive wine and beer list, plus classic cocktails like a barrel-aged Manhattan.

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23. Henry's Swing Club 18 W Hubbard St, Chicago, IL 60654 (River North)

This River North hub is home to over 22 slider options on its menu, as well as serious drink options (buy a bottle of Jack and get free Coke refills all night!), playing cards, vintage Playboys, and pool tables.

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24. Municipal Bar + Dining Co. 216 W Ohio St, Chicago, IL 60654 (River North)

This upscale sports bar is very much inspired by the streets of Chicago, with gritty murals depicting El tracks and drawbridges, a concrete bar, and 35 flat screens. In addition to their brews and cocktails, Municipal Bar also serves up some seriously good grub like the chorizo gourmet burger, sliders, and loaded fries.

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25. Oak + Char 217 W Huron St, Chicago, IL 60654 (River North)

Staying true to its name, the space sports plenty of oak, as well as billowy light fixtures that look like plumes of smoke. Feast on ultra-flavorful "M.S.G." wings (trust us, it’s not what you think) and a smoky double-patty burger, or go big with a market price 32oz bone-in ribeye served with bone marrow and sauce Perigueux on a badass wooden board.

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26. The Stretch Bar & Grill 3485 N Clark St, Chicago, IL 60657 (Wrigleyville)

Fourteen TVs and two video walls ensure that you won't miss the game at The Stretch, while a delicious assortment of burgers, beers, and mason jar cocktails (available in 13, 32, 64, and 128oz versions!) ensure that you don't go hungry or thirsty, either.

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27. Pippin's Tavern 806 N Rush St, Chicago, IL 60611

Quintessential Irish tavern with $2 well cocktails and domestic drafts during happy hour.

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28. Streeter's Tavern 50 E Chicago, Chicago, IL 60611 (River North)

Escape the madness of the Mag Mile at the self-proclaimed "Greatest Bar Below Earth", whose ample basement-style entertainment includes pool, foosball, and a drinking-games-friendly ping pong table, and whose ample winter warmers include Rumple Minze'd cocoa, though don't tell your woman you were getting boozed up with some Swiss Miss.

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29. Mahoney's Pub & Grille 551 N Ogden Ave, Chicago, IL 60642 (West Town)

Mahoney's is king at elevated bar food, and we're not talking about peanuts in fancy bowls. Soak up their expansive beer menu with tequila pasta, Irish whiskey steak, or good ole' fried pickles.

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30. Rogers Park Social 6922 N Glenwood Ave, Chicago, IL 60626 (Rogers Park)

Rogers Park Social epitomizes the idea of a "neighborhood" watering hole, because it's actually founded and operated by neighborhood residents, who serve up inventive cocktails and craft beers inside a homey, industrial space. There's also a retro lounge where you can play games like Monopoly while you sip on bar favorites, such as the Socialite (St. George California Citrus Vodka, agave, lime, cranberry, Napoleon Mandarine Orange Cognac) or the Super Rad (CH Key Gin, Stiegl Grapefruit Radler, Pür Likor Elderflower Liqueur). It's a social spot, so bring plenty of friends, or go alone and get to know some of the locals.

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31. Castaways Bar & Grill 1603 N Lake Shore Dr, Chicago, IL 60614 (Lincoln Park)

Located at North Avenue Beach, this bar and grill serves american classics (think burgers and sandwiches) along with a full menu of island worthy umbrella drinks, from daiquiris to margaritas. In addition to incredible lake views, this bar-on-a-boat has South-Beach style cabanas you can rent out to privately sip your very tropical drinks. Of course, this place is a hot spot during the summer, so come early to grab a good spot to take in the sun and sand.

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32. Landshark Beer Garden at Navy Pier Varsity Shop, 700 E Grand Ave, Chicago, IL 60611

Bavarian beer and bar bites, say that three times fast.

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33. Mercat a la Planxa 638 S Michigan Ave, Chicago, IL 60605

The South Loop’s Mercat a la Planxa brings the Mediterranean to Michigan Ave from its post at the Renaissance Blackstone Hotel. The menu is replete with Catalan-inspired tapas and cocktails from famed Spanish Chef Jose Garces. Start with a variety of cured meats (read: Jamón ibérico) and a pitcher of sangria before moving on to tapas like boquerones and pulpo con patatas. Finish with classic large-format items like paella and cochinillo asado (the latter of which must be ordered 72-hours in advance -- it is a whole suckling pig, after all).

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34. Heaven on Seven 111 N Wabash Ave, Chicago, IL 60602

Cajun and creole cooking, check out their happy hour for mini hurricanes for $6 + $2 mini po'boys.

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35. Bascule Wine Bar 1421 W Taylor, Chicago, IL 60607

This quaint Taylor Street find brandishes some 135 wines. Despite its location, you’ll find that the wine list spans far beyond just Italian varietals. Pick a bottle that suits your taste and pair it with a BLT3 (pancetta, prosciutto, and applewood smoked bacon) or line-caught yellowfin tuna, encrusted in coriander, splashed with a bouillabaisse vinaigrette, and finished with chickpeas.

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36. Tavern on Little Fort 4128 N Lincoln Ave, Chicago, IL 60618

Saloon vibes and sando bites. Sip on a cold brew amongst the antiques.

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37. Carnivale Restaurant 702 West Fulton Market, Chicago, IL 60661 (West Loop)

Carnivale... exactly as it sounds! This Latin American hub is doling out delicious ceviches, steaks, and zesty 'tails.

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38. Momotaro 820 W Lake St, Chicago, IL 60607 (West Loop)

Momotaro is Fulton Market’s 11,000sqft, three-story, high-end Japanese restaurant from Boka Restaurant Group. And it should come as no surprise that the menu, like the restaurant itself, is enormous: it is a daunting multiple-page list with myriad options (order with purpose) and obscure ingredients (pay attention, heed your server’s advice, and keep your smartphone handy). There are a dozen categories to navigate, among them Kushi Yaki, Rice and Noodles, Nigirizushi, Makimono, and Donburi Bowls. Decisions are best made over cocktails (or sake, wine, or Japanese whiskey), which are available both in the dining room and at Izakaya Lounge, the subterranean late-night bar below the restaurant. Momotaro is a destination for an immersive, modern Japanese experience; go hungry, choose wisely.

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39. The Ogden 1659 W Ogden, Chicago, IL 60607 (West Loop)

This United Center-friendly sports bar permeates industrial-chic by mixing a fireplace-equipped lounge with flatscreen-appointed booths, setting the stage for next-level bar eats like whipped salt cod tacos, truffle mac & cheese, and garlic buffalo wings in portions so hefty, you might need to take them to go. They're also sporting a lineup of 20 local craft beers on tap, and even more by the bottle.

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40. Nellcôte 833 W Randolph, Chicago, IL 60607 (West Loop)

Nellcote was named after the mansion on the French Riviera in which The Rolling Stones recorded Exile on Main Street, and it bears all the trappings that you'd expect for a place connected to such fame and splendor. Beyond the fanciful decor, this restaurant features an eclectic menu ranging from pizza and pasta, to wood-grilled chicken and pork belly confit.

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41. The Franklin Room 675 N Franklin St, Chicago, IL 60654 (Near North Side)

This whiskey-focused tavern is from the Union Sushi + Barbecue folks, who're doing classic comfort food like chick-fried ribeye, fried bologna, and Reuben sandwiches, as well as a healthy selection (as in, large amount-healthy, not, like, healthy-healthy) of cheese and charcuterie boards.

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42. TÊTE Charcuterie 1114 W Randolph St, Chicago, IL 60607 (West Loop)

TÊTE has that something extra -- actually, multiple somethings extra. There's a dedication to making sure all the selections -- peppery coppa, rich fromage de tête, silky duck rillette -- are all given the proper attention. There're also international encased meats from French boudin blanc to Moroccan merguez that'll push you further toward your meat coma, plus dishes like Peking duck with white miso and rutabaga mostarda that don't seem to really fit the concept, but are too tasty for anyone to get upset.

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43. MAK Restaurant 1924 W Division St, Chicago, IL 60622

Modern Chinese cuisine meets laid-back bar vibe.

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44. Umami Burger Wicker Park 1480 N Milwaukee Ave, Chicago, IL 60622 (Wicker Park)

LA-based burger chain Umami Burger has arrived in Chicago via Milwaukee Ave. Here, each patty is seared, topped with special Umami seasoning, and cooked to medium rare (plus, the toasted Portuguese-style bun features a branded "U" on top). Try the Manly Burger made with beer-cheddar, bacon lardons, and smoke-salt onion strings. Or, exclusive to the Chicago shop, the Calabrese Burger that digs into the city's love of sausage with a calabrese sausage patty, fondued truffle cheese, and house-pickled giardiniera. Sides include fries, tempura battered onion rings, four dipping sauces. The Un-Beef menu section provides a sushi-grade ahi tuna burger with daikon sprouts, crushed avocado and gingered carrots. But possibly best of all, the street art-tagged interior houses a full bar with a whiskey wall that goes 70 varieties deep, plus 20 beers on draft or in bottles.

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45. Furious Spoon 1571 N Milwaukee Ave, Chicago, IL 60622 (Wicker Park)

Shin Thompson's small-but-mighty Furious Spoon in Wicker Park stands well above the rest of Chicago's ramen shops for its bowls of handmade noodle soups. The menu features a few kinds of ramen with suggested toppings, like the house apple chili sauce. The signature Furious Ramen, a soul-warming blend of tonkotsu broth and spicy miso, pairs well with a Surly Furious Beer. The restaurant is sleek and narrow with a minimalist, artsy vibe that fits in perfectly with the trendy neighborhood.

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46. The Hampton Social 353 W Hubbard St, Chicago, IL 60654 (River North)

This seafood spot is a laid back scene with a great brunch and killer happy hour with $89 dollar magnums and half-price glasses of rosé and pizza from 4-7pm on weekdays.

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47. Chop Shop 2033 W North Avenue, Chicago, IL 60647 (Wicker Park)

Wicker Park's hybrid butcher shop/eatery/salumeria serves up stand-out, meat-oriented American fare such as the deli's Porchetta sandwich, a housemade pork loin wrapped in pork belly with asiago, arugula, apricot marmalade, and tomato on your choice of 7" or 12" French, white, or wheat bread. CS is a spacious joint -- a whopping 6,000 square foot event space -- so it's also great for hosting parties or business meetings.

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48. Fabulous Freddies Italian Eatery 701 West 31st St, Chicago, IL 60616 (Bridgeport Sox)

This Bridgeport pizza/sub joint covers all the classic Italian bases, from steak sandwiches to Italian ice. Like most of the sandwiches here, the beef is a monster, densely packed with lots of meat and the house giardiniera.

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49. Pearl's Southern Comfort 5352 N Broadway St, Chicago, IL 60640 (Edgewater)

Pearl’s serves mouth watering Cajun and Creole cuisine in a casual, comfortable Edgewater joint. It’s a perfect spot for low-key date nights or family outings. On warmer days, dine on the rooftop for spectacular views of the city. The friendly staff will make you feel right at home, whether you’re a local or out-of-towner.

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50. Kit Kat Lounge & Supper Club 3700 N Halsted St, Chicago, IL 60613

Drag-queen divas perform nightly at this upscale American restaurant. KKL is equally as famous for their extensive cocktail list— they’re always adding drinks, divas and decor to the place, so you’re always set for an over-the-top, unlike-any-other night out. This spot is especially popular for bachelorette parties, girls nights out' or boys night out (really). Happy hour is 5:30-7pm everyday, but stop in Monday and Wednesday for special deals like half-priced martinis and half-priced cocktails.

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51. Commonwealth 2000 W Roscoe St, Chicago, IL 60618

Hints of industrial Americana shine through amongst the food, libations, and good ol' fashioned cups of Joe offered here.

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52. mEAT Chicago 3339 N Halsted St, Chicago, IL 60657 (Lakeview)

MEAT specializes in skewered menu items and imaginative cocktails. Their skewers are meant to be ordered like sushi— creative, gourmet menu items, cut in bite-sized pieces, uniquely presented for family-style serving. Each diner gets their own tongs to select the scrumptious bites of their choice. Using foams, whipped creams, carbonation and gels, their cocktails put a twist on the familiar drinks in order to liven up traditions.

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53. New York Wing Factory 2464 N Lincoln Ave, Chicago, IL 60614 (Lincoln Park)

This is Lincoln Park’s go-to place for wings, offering menu items for meat-lovers and vegetarians alike. With a large range of appetizers, entrees and desserts, you’ll be back again soon. The Wing Factory uses fresh chicken from a medium wing that’s never frozen or preserved, and then is fried twice for extra crisp. It's all topped off with signature sauces like soy garlic, spicy soy garlic, and traditional housemate sauses like buffalo, hickory BBQ, and jalapeno BBQ.

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54. Sedgwick's Bar & Grill 1935 N Sedgwick St, Chicago, IL 60614 (Lincoln Park)

Stop in this neighborhood bar that serves mouth-watering burgers, sandwiches and Mexican fare with hearty sides. It’s welcoming atmosphere will make you feel like a regular from the moment you walk in the door. Service is attentive and drinks are strong. There are plenty of TVs for game time, too.

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55. Osteria Langhe 2824 W Armitage Ave, Chicago, IL 60647 (Logan Square)

This Logan Square spot seamlessly blends slow food (literally, there's snail confit) with fine wines, all while transporting you to the northern Italian countryside. Expect rich dishes like prosciutto-wrapped rabbit loin and hand-pinched ravioli tossed with Parmesan, thyme, and butter. You'll want to grab a table in the Giardino Segreto ("secret garden" in Italian), but heads up: you'll need a reservation to dine on this lovely patio, so be sure to plan ahead.

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56. Bar Allegro 171 W Randolph St #101, Chicago, IL 60601

Mood-lit hotel bar with a jazzy personality.

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57. Old Town Pour House 1419 N Wells St, Chicago, IL 60610 (Old Town)

Taking over the former 33 Club, OTPH-no-J is a wood-ensconced bi-level brew hall with wall-to-wall flatscreens and 120 taps, which pour out suggested pairings for truffle mac 'n cheese w/ Guinness-braised short ribs (uhhhh... Guinness?), blackened red snapper tacos w/ cilantro-lime cream, and crab fondue infused with Humboldt Fog.

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58. Harry Caray's Italian Steakhouse 33 W Kinzie St, Chicago, IL 60654 (River North)

Housed inside a landmark building that was once home to Frank Nitti, the notorious enforcer of Al Capone’s gang, this storied steakhouse is named for the famous sportscaster Harry Caray. It serves a wide variety of prime cuts and Italian-American dishes, but the thing to order is the chicken Vesuvio, a Chicago-born speciality made with roast chicken, garlic, and white wine. A giant mural of Caray beside the building will be the beacon that leads you to this buzzy, River North institution that's a time capsule of sports memorabilia and relics of the gangster-era.

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59. Nick's Fishmarket Grill & Bar 222 Merchandise Mart Plz, Chicago, IL 60654 (River North)

Nick’s is a seafood restaurant with a modern, blue-lit bar, accented by glass walls and blue decor. For lunch, there's a three-course prix fixe of a soup/salad, an entree and a dessert $22. Stop in Monday, Wednesday and Thursday for an extra long happy hour (2-7pm) featuring $4 draft beers, $6 select wines by the glass, $7 cosmos, $1 oysters, and $5 light bites.

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60. Pi Gallery Bar 738 N Clark St, Chicago, IL 60654 (River North)

Check out this art-centric cocktail lounge that overlooks the historic Clark St. in Chicago's River North. Menu items include Neapolitan-style pizza and craft cocktails. Stop in and see rotating local art.

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61. Division Ale House 1942 West Division St, Chicago, IL 60622 (Wicker Park)

Nothing says Celtic-authenticity quite like 80oz beer towers and Guinness-spiked mac and cheese.

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62. The Betty 839 W Fulton Market, Chicago, IL 60607 (West Loop)

Right next to The Publican, this neighborhood tavern in West Loop is upscale enough to impress clients but casual enough to take a first date. The dimly lit, rustic space is decorated with vinyl-stacked bookcases and red leather sofas, and something about the retro vibe creates a perfect ambience to drink fancy cocktails and small bites than run the gamut from chicken liver mousse to pierogies. Drinks range in price -- there's 23-year Pappy Van Winkle, but there are also half-price beers when the happy hour time is right.

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65. III Forks Prime Steakhouse 180 N Field Blvd, Chicago, IL 60601 (Loop)

III Forks Steakhouse is a contemporary steakhouse nestled in Chicago’s Lakeshore East. With a lively bar/lounge area and beautiful views overlooking the park side—not to mention the array of over 3,000 fine wines from the spectacular glass wine room—this spot is perfect for special occasions or after-work drinks. The menu features USDA Prime beef and ocean-fresh seafood.

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66. Ph.D Pub Chicago 1257 S Halsted St, Chicago, IL 60607

This UIC bar’s patio is a University Village outdoor favorite and features picnic tables, lounge chairs, and couches for your outdoor boozing comfort. Designed with a 1920s mahogany bar and stained glass touches throughout the bar, the casual and cozy haunt seamlessly adds to the historic Maxwell Street's repertoire of friendly dining and retail offerings. Stop in for a craft brew in the beer garden, or a vodka lemonade that'll evoke summer on any month of the year.

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67. The Boundary 1932 W Division St, Chicago, IL 60622 (Wicker Park)

Contrary to its name, The Boundary is actually a very welcoming neighborhood spot. They serve lunch and dinner, and have a beer menu with over 120 options.

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