The Haute Seeker

Haute Happy Hour: Chicago Food and Drink Specials October 2019

Sushi from Roka Akor featured on The Haute Seeker Happy Hour

The fall season is officially here! To celebrate the occasion, I am sharing some of the most popular Haute Happy Hour picks from the summer season. Check out the roundup of October happy hour as well as food and drink specials. This month’s list roundup features downtown go-to’s and rooftop favorites for those of us who can’t bear to say ‘good-bye’ just yet.

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.


River North – Highline Bar Chicago, 169 W Kinzie St.

Highline Bar offers the perfect remedy for the ‘Monday blues.’ Highline Bar offers a burger, beer, and a shot for only $10 every Monday. The popular bar and restaurant are located just steps away from Merchandise Mart located in the River North area of Chicago. Check out the website for more daily food and drink specials.

Daily specials are offered Sunday through Saturday. Be sure to check the website for more details on special offers.

The Loop – Elephant & Castle, 111 W Adams St. 

Located close to many downtown office locations, Elephant & Castle offers a unique array of food and drink specials inspired by British fare. Specials at this Loop bar includes select draught beers for $4, 6 oz. House wine for $4, and 1/2 price Snacks & Share dishes such as Pretzel Bites, Steamed Mussels, and Castle Nachos.

Happy Hour specials are available on Mondays – Fridays from 3:00 p.m. – 6:00 p.m.


West Loop – Mad Social, 1140 W Madison St. 

Enjoy a bite of contemporary flair in the West Loop this October. Happy hour specials at Mad Social include half-off meat and cheese boards as well as half-off select bottles of wine every Tuesday. Can’t make it on a Tuesday? This special is also available on Thursdays.

Happy Hour Specials are available Monday through Friday, from 4:00 p.m. – 6:00 p.m.

River North – Roka Akor, 456 N Clark St. 

Get your fix of sushi, dumplings, and more at Roka Akor. The upscale Japanese restaurant located in River North offers a variety of daily happy hour specials. Try dishes such as the Wagyu Beef and Kimchi Dumplings for $5, Signature Tataki Trio: Butterfish, Tuna, and Yellowtail, Lobster & Shrimp Dumplings, or Crispy Fried Squid with Chili and Lime for $6. Drink specials vary from Sapporo Draft for $3 and House Infused Shochu for $5.

Happy Hour Specials are available Monday through Friday, from 5:00 p.m. – 6:00 p.m. and is available in the patio and lounge only.


West Loop – Eleven Eleven, 1111 W Lake St.

Wine down, every Wednesday night with food and drink specials from Eleven Eleven. The West Loop wine bar specializing in pairings offers a different selection of wines and foods daily. Enjoy food plus a glass of wine for $11.11 or 1/2 off on select wine offerings. Other specials include $20 food and wine pairings.

Happy Hour specials are available Tuesdays – Fridays from 5:00 p.m. – 8:00 p.m.

Near North Side – ZED 451, 739 N Clark St. 

The legendary happy hour menu at Zed 451 continues this month in Chicago. Enjoy the Wednesday special of half-off wine by the glass plus $4.51 food specials at this Brazilian Steakhouse on the Near North Side.

Happy Hour Specials are available Monday through Friday, 4:30 – 6:30 p.m. in the bar/lounge unless otherwise indicated.


West Loop – City Mouse, 311 N Morgan St.

Working in the West Loop? Stop by City Mouse at the popular Ace hotel for food an drink specials. The ground floor hotel restaurant and lounge, City Mouse, offers a low-key environment for both work and play. Specials include snacks such as $6 Fries and $14 Spicy Fried Chicken Wings, as well as ‘Deals of the Day,’ for beer, cocktails, and bites.

Happy Hour Specials are available Monday through Friday, from 3:00 p.m. – 5:00 p.m., and are available in the patio and lounge only.

West Town – Bar Biscay, 1450 W Chicago Ave. 

One more day closer to Friday—why not enjoy a classic cocktail to get the weekend started, right? Every Thursday from 3:00 p.m. until close, Bar Biscay offers three classic cocktails for $7 each. Save your club card for a free cocktail on any other Cocktail Club night (with food purchase).

Food and drink specials are available on Tuesdays, Wednesdays, and Thursdays.


South Loop – SX Sky Bar, 808 S Michigan Ave. 

The popular South Loop bar continues to make a name for itself this fall. The SX Sky Bar offers food items such as $16 Sky Bar Sliders, $5 Truffle Fries. For drinks, enjoy $8 glasses of House wine and $9 Prosecco.

Happy Specials are available Monday through Friday, from 4:00 p.m. – 7:00 p.m. Happy Hour specials are available from 4:00 p.m. – 12:00 a.m. on Wednesdays.

West Loop – La Josie, 740 W Randolph St. 

La Josie, the popular, family-owned Mexican restaurant, puts the “yay” in Friday. This October, stop by the West Loop hot spot for 50% off of Margarita’s, Tacos Dorados, and Salsa.

Happy Specials are available Monday through Friday, from 4:00 p.m. – 6:00 p.m.

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

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