The Haute Seeker

Haute Happy Hour: Chicago Food and Drink Specials December 2019

holiday themed milkshake

It’s the most wonderful time of the day. Happy Hour. This month’s roundup includes holiday-themed bars, food, and drinks specials that will certainly help to make the season bright.

The key phrase in happy hour is ‘happy.’ So, keep in mind that menus are subject to change, as many menus often do because of seasonality and availability. Be sure to contact the restaurant or visit their website for additional details before heading out to the happy hour of your choosing.


Wrigleyville – Santa Baby Bar3505 N Clark St.

The holiday-themed bar in Wrigleyville has everything you need to make your happy hour happier. Santa Baby Bar features wall-to-wall Christmas decor & multiple bars plus beer, cocktails, & DJs. Stop by this holiday bar for movies every Monday, starting at 7:00 p.m. For more specials and events at this bar, visit the website.

Daily specials are available Sunday through Friday. Time and specials vary.

River North – Broken Shaker, 19 E Ohio St.

Broken Shaker is a hip cocktail bar in River North that is a fantastic place to experience a Monday happy hour in Chicago. Food and drink specials include the Chef’s Burger, Fries, and a Domestic Brew for only $15.

Happy Hour specials are available on Mondays through Friday from 4:00 p.m. – 6:00 p.m. 


West Loop – Cabra200 N Green St

From the creative mind of Chef Stephanie Izard, Cabra is a Peruvian-inspired restaurant featuring a happy hour to match its unique location in the West Loop. Located on the rooftop of the Hoxton hotel, this restaurant features $5 – $8 food and drink specials. Savor items such as $5 Yuca Fritas, $6 Salmon Huancaina Dip, as you sip on $7 Sparkling Brut or and $8 Lima Dreamin’, a specialty house cocktail.

Happy Hour food and drink specials are available Monday – Thursday, from 4:00 p.m. – 6:00 p.m. Menus are updated frequently, be sure to check with the restaurant on daily specials.

West Loop – Poltian Row111 N Aberdeen St

Taco Tuesday is better with a tequila-based cocktail in hand—at least at Politian Row. Every Tuesday, the industrial style food hall located in the West Loop offers $3 Tacos from Tolita and $8 Margaritas or Tequila Mules from Bar Politan. Additional Tuesday food and drink deals include $8 Bloody María’s, and $9 Totopos y Queso. This special is available all day long.

Food and drink specials are available Monday – Friday from 11:00 a.m. – 10:00 p.m. Offers will vary depending on the day.


The Loop – Flight Club111 W Wacker Dr.

Enjoy an after-work game of darts and drinks at Flight Club in the Loop. Every weekday, the downtown bar and social darts venue features a menu of food and drink specials that are $5 and under. Drinks range from $5 Domestic Bottles and specialty cocktails, while food specials include Oysters on the Half Shell and Shrimp Cocktail for $1.50 each.

Happy Hour specials are available Monday – Friday from 4:00 p.m. – 6:00 p.m.

Portage Park- Sutherland’s Food and Spirits5353 W Irving Park Rd.

Every Wednesday is an excellent day for Happy Hour at Sutherland’s in Portage Park. The neighborhood pub offers 50 cent wings (min 6) with the purchase of a drink each Wednesday. Wings, not your thing? Check out their other daily food and drink specials ranging from discounted drafts to low-priced appetizers.

Food and drink specials vary. Check out Sutherland’s Facebook page for daily deals.


River North – Hub51, 51 W Hubbard St. 

Hub 51, the River North bar and lounge, offers hand-rolled sushi for half price daily. Savory, simple, and to the point.

Happy Hour is available from 3:00 p.m. to 6:00 p.m. and after 11:00 p.m.

The Loop – Free Rein, 224 N Michigan Ave.

Grab bites and drinks from the St. Jane Hotel’s American bistro Free Rein. Located on Michigan Avenue in The Loop, Free Rein offers $5 Prosecco, Avocado Tartine with Shaved Vegetables, House French Fries with Grated Parmesan, and more.

Daily specials are offered Monday through Friday from 4:30 p.m. – 6:30 p.m. Specials are only available at the bar. Be sure to ask your server for daily selections.


The Loop – Latinicity, 108 N State St.

Celebrate the end of the work-week with drinks at Latinicity in The Loop. Located on the 3rd floor of Block 37, the Latin-fused food hall and bar offers daily drink specials for solo drinkers or large groups. Enjoy $4 Cerveza’s, $6 house cocktails such as a Traditional Margarita or Paloma

Happy Specials are available at the bar Monday through Saturday from 4:00 p.m. – 6:00 p.m.

River North – Jake Melnick’s41 East Superior Street

Stop by Jake Melnick’s for happy hour every weekday in Chicago. The River North restaurant serves up a $5 food menu including BBQ Chips, Fried Pickles, Mini Corn Dogs, Kettle Corn, Fried Olives, and a Meat & Cheese Board. You’ll also find select draft beers for $6, choose cocktails for $7, and wine for $8. 

Happy Hour specials are available Monday – Friday from 4:00 p.m. – 6:00 p.m.

Need more food and drink specials choices? Check out past Haute Happy Hour deals for more after-work options.

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