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The 7 Best 'Happy Hour' Specials In Chicago

By Chuck Sudo in Food on May 14, 2014 9:00PM

Last year we ran a list of our favorite "Happy Hour" specials across Chicago. We parantheticaled "happy hour" because, as we noted last year, the Illinois Happy Hour Law lists what an establishment can and cannot do to attract an after-work clientele.

To wit:

- "$5 all you can drink," "$5 unlimited beer from 5:00 to 7:00 p.m.," etc., promotions are prohibited.

- Reducing or fluctuating prices during normal operating hours (from open to close). Prices must be the same for all customers, for all purchases for the whole day.

- Promotions such as: 8oz. beer is $1.00 and 16oz. beer is $1.25 (double the alcohol means double the price), or Double the shot in your drink for $.25 more are prohibited.

Here is what the Happy Hour Law does allow.

- Selling pitchers (or the equivalent, including but not limited to buckets, carafes or bottles) of alcohol, customarily sold in that manner and delivered to 2 or more persons.

Offering free food or entertainment.

Including drinks as part of a meal package.

Let's review. Drink specials during a specific time frame bad. Drink specials offered all night good. Drink specials offered as part of a meal package better. Free food? Jackpot!! Pass "Go." Collect $200.!

Take a look at last year's list, add these seven picks and you have a nice list of after-work specials.

Duck confit pasta and a cocktail at Two.

Two was already a great place for after work drinks, but this week they introduce a $12 special on Tuesday night that gets you a bowl of their delicious duck confit pasta and one of their well-crafted signature cocktails. The cocktails alone regularly cost from $12 to $16, so this is a great deal. — Melissa McEwen

Two is located at 1132 W. Grand Ave.

Blue Line Lounge & Grill
Back when I was working my first office job after college, a favorite pastime between bored co-workers was of course drinking. Which meant during lulls between projects we all would spend our time looking for some of the best cocktail specials around the city. One place our group of office friends ended up time and time again was Wednesday or Thursday nights at Blue Line. First off, the location is perfect since it is literally underneath the Damen Blue Line stop. Which is the perfect distance for stumbling home after a night of $5 martinis, which is every Wednesday night. You can get classics but if you like what I refer to as “candy booze” you are in luck. Their house secret peanut butter and jelly martini is a delicious dessert in a glass. If you are more a mojito fan, stop in Thursday when their full list of specialty mojitos are just $4. My favorite is the coconut and raspberry. Sangria pints are only $3 on Thursday as well. I’ve had really hit or miss food here, so I usually drink up then head to Big Star’s to-go window after for some tacos. It’s a perfect midweek combination to soothe your office blues. — Lisa White

Blue Line Lounge & Grill is located at 1548 N. Damen Ave.

Table, Donkey and Stick
Table, Donkey and Stick offer a pretty sweet deal to soften the blow of just another manic Monday. If your weekend felt too short, you will surely need a drink or two come Monday evening. And TDS wants to make sure your week starts off right. Each Monday they offer a rotating menu of $5 food specials along with .50 cent PBRs and $3 bourbon shots. The food specials usually include a creative take on a burger (recent offerings include grilled ramps on top), and comfort favorites like braised pork meatballs, stuffed mushrooms and mac & cheese with gnocchi. They even slide a dessert on there, such as the recent offerings of apple fritters with sage powdered sugar or pecan pie with Armagnac whipped cream. If it is later in the evening and/or not a Monday at all, you can now enjoy their Wanderteller, a selection of meats and cheeses, for half off at the bar only after 9 p.m. on weekdays. My favorite picks include the duck liver mousse and the Hudson Red cheese. — Lisa White

Table, Donkey and Stick is located at 2728 W Armitage.

Cleo’s and Jack & Ginger’s
Cleo’s in Ukrainian Village and Jack & Ginger’s in Bucktown (formerly a Cleo’s) both have great food and drink specials that change daily, giving you good reason to stop by and enjoy their spacious patios. With multiple specials each day, the full list is way too long to include here, but here are some popular deals to give you an idea: $3 “J” shots (Jameson, Jack Daniels, Jim Beam, J├Ągermeister & Jose Cuervo) on Wednesdays, half priced appetizers on Tuesdays (J&G only), $1.50 Taco Tuesday (Cleo’s only), $1 sliders on Saturdays and $4 Bloodys and Mimosas on Saturdays and Sundays. That’s right, they still have specials on the weekends, too, unlike a lot of places who limit them to the work week to lure you in when business is slow. Jack & Ginger’s opens every day at 4 p.m. (11 a.m. on weekends), and Cleo’s is open at noon during the week and even earlier on the weekends for you soccer fans to watch those international match-ups. Speaking of sports, both bars are big Chicago fans so they’ll always have the big Hawks/Bulls/Bears/Cubs/Sox game on. Both locations have a trivia night, too (Tuesdays at Cleo’s, Wednesdays at J&G) as if you needed another excuse to come in. — Michelle Meywes

Cleo’s is located at 1935 W. Chicago Ave. and Jack & Ginger’s is at 2048 W. Armitage.

This Pilsen gastropub offers a variety of great weekly specials including their Tuesday $15 BBB (Burger, Beer, Bourbon), which showcases their burger, easily the best item on their menu, and their excellent beer selection. Plus you get some bourbon, because why not? On Wednesdays they feature a different $5 cocktail every week, which is usually something Latin-inspired with tequila or mezcal. — Melissa McEwen

Pl-Zen is located at 1519 W. 18th St.

Brisku’s Bistro
Brisku’s Bistro is a little bit off the beaten path, so it might not be ideal for an immediate after-work stop, but if you’re looking to go home, get a quick change and catch up with some folks to watch a Blackhawks, Bulls or White Sox game (sorry Cubs fans, but you might want to find another joint), then Brisku’s ain’t a bad option. Don’t freak out. It’s a chill place that won’t turn bro-hemian on you. With a variety of daily specials, you’ll be sure to find something you like. Specials range from $2 ┬╝ lb burgers with fries (Tuesdays), 50-cent jumbo wings (Mondays and Sundays), half-price bottles of wine (Wednesdays) and $5 all-you-can-eat pasta (Fridays). There are different beer specials each night, too. If catching a game isn’t your gag, then you might just want to relax tossing some darts or shooting some pool.— Casey Moffitt

Brisku’s Bistro is located at 4100 N. Kedzie Ave.

Lone Wolf Tavern
This Randolph Street stylized dive from Heisler Hospitality (the folks behind Trenchermen, Bangers & Lace and Nightwood, among other trendy restaurants), the folks from Barrelhouse Flat and Pleasant House Bakery’s Art and Chelsea Jackson is Chicago’s unofficial Three Floyds beer bar, with four of their eight draft lines serving brews from the Munster, Ind. brewery. But did you know you can order a Three Floyds beer and one of Pleasant House’s Royal Pies for a cool $10? Now you do. Lone Wolf carries Pleasant House’s standard mushroom and kale, chicken balti and steak and ale pies as well as two others you won’t find at their Bridgeport shop. The “Mac Daddy” is a stellar carbohydrate bomb with mac and cheese, bacon and onion. The “Cowboy Queue” features beef brisket marinated in Pleasant House’s queue sauce and lima beans. If you can’t get a seat at Au Cheval, Girl & the Goat or any other Randolph Street hotspot, this special is a fine alternative. — Chuck Sudo

Lone Wolf Tavern is located at 806 W. Randolph St.