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CHI Spring Happy Hour Guide

It’s been less than a year since happy hour was legalized in Chicago, but the city’s restaurants and bars have quickly picked up on the tradition that’s been giving professionals around the world something to look forward to after work. Now that the weather is warming up, Bitches are coming out of winter hibernation mode and are more inclined to stay out after work. Hit up these happy hours in the neighborhood where your work or live for a few cocktails!

River North
Not only does Hampton Social have a fantastic brunch selection, but they also have great happy hour specials. You can sip on rosé and enjoy their house-made pizza for half-price during happy hour. You’ll feel like you’ve taken a vacation in their tasteful, nautically themed dining room. Happy hour is available Tuesday through Friday from 3 p.m. until 6 p.m. Check out their menu here353 W. Hubbard St.


Beatrix River North is one of the Bitches’ go-to meeting spots. This all-in-one restaurant, bar, and cafe serves $7 spiked versions of their fresh-squeezed juices during happy hour. The blueberry and basil juice is a surprising yet delicious combination. Happy hour is available Monday through Friday from 3 p.m. until 6 p.m. For more information, visit here519 N. Clark St.

Soaring above the Dana Hotel on its 26th floor, Vertigo Sky Lounge provides guests with great views of River North. Sushi lovers will enjoy the happy hour menu, which includes $5 citrus salmon maki, $7 spicy tuna maki, $6 hamachi maki, and $2 beef sliders. 2 W. Erie St., (312) 202-6060 – Happy hour is available Monday through Friday from 4 p.m. until 7 p.m.

Oak & Char is a great River North spot that serves creative new-American dishes. Sample some of Oak & Char’s cuisine during happy hour on the 56-seat patio. Happy hour specials include $4 craft beer drafts, $2 Miller High Lifes, $8 house cocktails, $6 wings, and $8 burgers. 217 W. Huron St., (312) 643-2427 – Happy hour is available Monday through Friday from 4:30 p.m. until 6:30 p.m.

photo courtesy of RedEye
photo courtesy of RedEye

Union is the perfect happy hour for the hungry Bitch. Happy hour food specials include $1 oysters, $4 shrimp tempura rolls, and $2.50 beef filet skewers. Wash these bites down with a refreshing $5 Union Moscow mule. Happy hour is available everyday from 5 p.m. until 6:30 p.m. For more information, visit here230 W. Erie St.

The Loop

Meli Cafe knows a thing or two about really making people happy in the late afternoon. This brunch destination in the Loop has different happy hour specials for each day of the work week. On Mondays you can treat yourself to $6 martinis. Select wine bottles are half-off on Tuesdays and Wednesdays. Come hungry on Thursdays and Fridays, as appetizers are half-off at the bar from 3 p.m. until 6 p.m. View all specials here 500 S. Dearborn St. 

Hop to the Hotel Allegro’s bar to enjoy discounted drinks daily. You can enjoy the cocktail of the day for $5. If wine is more your thing, you can sip on reds or whites for $5 a glass during happy hour. Happy hour is available everyday from 4 p.m. until 6 p.m. For more information, visit here171 W. Randolph St. #101

River Roast’s riverside patio in the heart of the city is the perfect spot for scenic after-work drinks. Enjoy $5 drafts and bites including rabbit toast, onion straws, and chicken liver mousse profiteroles. Martinis and old fashioneds are $7 during happy hour. 315 N. LaSalle St., (312) 822-0100 – Happy hour is available Monday through Thursday from 4:30 p.m. until 6:30 p.m.

West Loop

Nellcote’s “savant special” makes this classy establishment accessible to starving artists and Bitches on a budget. Ten dollars gets you a beer and one of Nellcote’s award-winning fork-and-knife pizzas. The deal gets even better: happy hour is available after work on weekdays, and pretty much all day Saturday and Sunday. This is reason enough to stop by several nights a week. Check out our brunch review of Nellcote here. Happy hour is available Monday through Friday from 5 p.m. until 7 p.m. and Saturday and Sunday from 11 a.m. until 7 p.m. View all of its specials here833 W. Randolph St.


The Betty’s happy hour delights both the hungry and the thirsty. For a few bucks, you can indulge in discounted spiced cauliflower, croquettes, and baba ghanoush from the “snax” menu, while sipping on $8 cocktails and wines, and half-price drafts. Happy hour is available Monday through Friday from 4 p.m. until 6:30 p.m. For more information, visit here 839 W. Fulton Market

People watch in the West Loop on La Sirena Clandestina’s patio. Come hungry, because this happy hour menu is full of cheap, but delicious, bites. During happy hour, the grilled chicken skewers, chicken red chimichurri, hanger steak green chimichurri, shrimp selano salsa, and holoumi cheese malagueta salsa are $4 each. Side dishes include $6 kale salad, $4 empanadas, and $3 fries. 954 W. Fulton Market, (312) 226-5300 – Happy hour is available Monday through Friday from 3 p.m. until 5 p.m.


The fun doesn’t end when Hutch’s daily brunch service stops at 3 p.m. Every weekday you can get $1 champagne, $2 well drinks, $3 drafts, $4 wines, and $5 craft cocktails in the bar area. Stay until 4 p.m. to take advantage of the half-price appetizers and flatbreads in until 6 p.m. Click here to read our brunch review of Hutch. Happy hour is available Monday through Friday from 3 p.m. until 6 p.m. For more information, visit here3301 N. Clark St.

Stretch Bar & Grill in Wrigleyville has several happy hour promotions during the week. On Thursdays you can get $2 tacos, $3 Coronas, and $8 mason jar margaritas. Join the “6 O’Clock Club” Fridays from 6 p.m. until 10 p.m., when $20 gets you cocktails, Miller Lite or Coors Light drafts, and a burger and fries or an appetizer. The fun doesn’t stop on the weekend. On Sundays, industry employees get 50 percent off their bill, while the rest of us can take advantage of $5 Bloody Marys and mimosas, and half-off bombs. For daily specials, head to their website here3845 N. Clark St. 

Guests can enjoy Barcocina’s outdoor dining area beginning in the late spring. Happy hour specials include shared plates dishes for $3-$5. The menu includes roasted brussels sprouts, jalapeno cornbread, baked goat cheese, and more. Drink specials include $3 Mexican beer and $6 margaritas. 2901 N. Sheffield Ave., (773) 687-9949 – Happy hour is available Monday through Thursday from 5 p.m. until 7 p.m.

Whether you’re sitting inside or outside, all patrons can enjoy the outdoors thanks to Flagship’s retractable garage door. Flagships weekly specials include $5 wines and $6 salads and wraps on Mondays, $4 Jameson and $7 burgers on Tuesdays, $2 tacos and $3 Mexican beers on Wednesdays, and happy hour drink packages on Fridays from 6 p.m. until 9 p.m. Visit Flagship’s site for more details. 1622 W. Belmont Ave., (773) 687-9949 – These all-day specials are available Monday through Wednesday and Friday.

Lincoln Park


Stella Bara, Summer House Santa Monica’s pizza-serving neighbor, has a happy hour that delights both the thirsty and the hungry. At the bar you can get $6 craft cocktails, $4 drafts, and $6 glasses of wine. For $3 each, you can sample toast topped with various meats, cheeses, and veggies. The whipped burrata and spicy tomato jam-topped toast caught our eye. Those with Celiac’s can indulge too, as there are gluten-free bread options too. Happy hour is available Monday through Friday from 4 p.m. until 6 p.m. and Saturday and Sunday from 11 a.m. until 4 p.m. For more information, visit here1954 N. Halsted St.

To celebrate its 30th birthday, Cafe Ba-Ba-Reeba has created a happy hour menu with its signature tapas at 1985 prices. This means that ordering all eight tapas would set you back about only $20. Pair that with $16 pitchers of sangria, $2.95 Estrella Damm draughts, and $1 pintxos (bite-sized tapas), and you’ll be having a feast without breaking the bank. Happy hour is available Monday through Sunday from 4 p.m. until 6 p.m., and Fridays and Saturdays from 10 p.m. until midnight. For the happy hour menu, visit here2024 N. Halsted St.

Logan Square

Longman and Eagle’s happy hour is perfect for beer lovers. During the workweek you can get $1 cans of PBR and $4 drafts of a rotating weekly selection. Longman and Eagle serves a mean daily brunch, so come back in the morning to give it a try. Happy hour is available Monday through Friday from 3 p.m. until 5 p.m. For happy hour specials, visit here2657 N. Kedzie Ave.

In addition to a half price house margaritas Mondays through Thursdays from 3 p.m. until 6 p.m., De Noche Mexicana has daily $6 drink specials. You can get discounted mojitos on Mondays, sangria on Tuesdays, margaritas on Wednesdays, and Caipirinhas on Thursdays. For more information. visit here2710 N. Milwaukee Ave.

Could there be a better place to enjoy nice weather than at Castaways on North Avenue Beach? Castaways opens for the season on May 6, just in time for beach weather. On Tuesdays, margaritas and limeritas are half-price. On Wednesdays visitors can enjoy $4 beers by the beach. On Thursdays, you and your Bitches can split a bucket of beers for $22. 1603 N. Lake Shore Dr., (773) 281-1200 – Happy hour is available Tuesdays from 4 p.m. until 8 p.m., Wednesdays from 3 p.m. until 6 p.m., and Thursdays from 5 p.m. until 9 p.m.

With garden seating and an extensive menu of daily specials, Derby is a beautiful spot to grab a drink and catch a game. On Mondays, Derby has sandwiches for $6 and select beers for $5. On taco Tuesdays you can get $2 and $3 tacos, and $3 Dos Equis drafts and bottles of Corona and Corona Light. On Wednesdays, burgers and beers are $5 each. Thursday night is ladies’ night; wind down with half-price bottles of wine, salads, and wraps. Friday specials include $6 PBRs and shots, $20 party bowls, and half-price appetizers. Along with weekend brunch, on Saturdays and Sundays visitors can get $3 mimosas, $5 Bloody Marys, and $5 “beermosas.” 1224 W. Webster Ave., (773) 248-0900 – Happy hour is available all day Saturday through Thursday. On Friday, happy hour is available from 5 p.m. until 7 p.m.


Bowling and bocce makes Bitches hungry. Thank goodness for Pinstripes’ happy hour menu, which offers extensive appetizer, pizza, and flatbread offerings for $5-$8. Top that off with $4 tap beer, $4 house wine, and $5 well drinks, and you have the perfect setup for after-work festivities. Bonus: Go to Pinstripes during happy hour on a Thursday for $6 handcrafted cocktails. Happy hour is available Monday through Friday from 3 p.m. until 6:30 p.m. For their full happy hour menu, visit here435 E. Illinois St.


DrumBAR is so much more than a hotel bar. Head to the Raffaello Hotel to get the full experience at DrumBAR’s happy hour. Specials include $8 DrumBAR cocktails and glasses of G.H. Mumm champagne. Happy hour is available Monday through Saturday from 5 p.m. until 7 p.m. For more information, visit here201 E. Delaware Pl.

Old Town

Old Town Social’s daily specials are sure to make every Bitch happy. Tuesdays are industry nights, so if you work in the business, your bill is half-price from 9 p.m. until closing. On Wednesdays, you can get $5 cheeseburgers and $3 cans of Goose Island beer. Thursdays feature $2 tall boys of PBR, Schlitz, and Old Style. Fridays from 5 p.m. until 7 p.m., you can enjoy $1 pulled pork sliders, $3 shots of Fireball, and $2 PBR drafts. For more information, visit here455 W. North Ave.


If you ask them, Old Town Pour House has the “craftiest” happy hour in Old Town. Deals include a $4 beer pick that rotates weekly and half-price wine bottles and beer bombers. Come back on the weekend for its “Bubbles and Beer” brunch. Happy hour is available Monday through Friday from 4 p.m. until 6 p.m. For more information, visit here1419 N. Wells St.

Wicker Park

Smoke Daddy has daily specials that make for a delicious happy hour experience. Mondays feature $4 drafts, as well as live blues or jazz music. On Tuesdays Smoke Daddy serves pulled meat nachos for $7. On Wednesdays, you can get $6 burgers. Come back on the weekend for its tasty, casual brunch.  For more information, visit here1804 W. Division St.


For a happy hour experience unlike any other, head to the Violet Hour for their L’heure verte (green hour) absinthe happy hour. During l’heure verte you can try several varieties of absinthe and absinthe cocktails. This stuff is strong, so go easy if it’s your first time having absinthe! Happy hour is available Monday through Thursday from 6 p.m. until 8 p.m. For more information, visit here1520 N. Damen Ave.


Nothing is better than happy hour with your best friends, human and canine included! Bring your furry friend to Lottie’s Pub, since dogs are welcome on the patio. At Lottie’s, Monday is trivia night, when tacos are $2, Dos Equis is $3, and Milagro is $4. On Tuesdays you can get $4 burgers, $3.50 on select pints, and $4 Jameson. On Wednesdays, chicken sandwiches are $4, select beer cans are $2.50, and select shots are $4. On Thursdays, you can get $4 beef sandwiches, $6 32-ounce servings of Coors or Miller, and $4 shots of whiskey or tequila. On Fridays, pair 50-cent jumbo wings with $4 Corona or Corona Light. The fun doesn’t stop on the weekend, when cheese pizza are $9, and on Sundays you can get mimosas for $4 and Bloody Marys for $5. 1925 W. Cortland St., (773) 489-0738 – Happy hour is available all day, every day.

Roscoe Village

At Commonwealth Tavern, the weekly specials take you into the weekend, making it the perfect spot to enjoy discounted drinks al fresco any day. On Mondays, wings are half price and microbrews are $5. On Tuesdays, you can get $4 pints of Blue Moon and $15 buckets of Miller or Coors. Wednesday is trivia night, as well as $5 seasonal beer day. On Thursdays, you can enjoy $6 glasses of wine, Moscow mules, and margaritas. Fridays are for $6 craft cocktails and half-priced appetizers. Come back on the weekends for brunch and $3 mimosas. 2000 W. Roscoe St., (773) 697-7965 – Happy hour is available all day Saturday through Thursday, and from 3 p.m. until 6 p.m. on Friday.

Noble Square

Frontier’s 2500 square foot beer garden is now open for the season. On Mondays at Frontier, you can enjoy oysters for $1 a pop. The “Fat Tuesdays” specials menu includes Creole favorites like gumbo and po’boys, as well as $5 Abita on tap. Enjoy whiskey and wine on Wednesdays with half-price Bulleit cocktails and bottles of wine. The highlight of the week is Thursday, when the patio campfire goes on and patrons can gather for free make-your-own s’mores and $6 hot cocktails. During weekend brunch, you can enjoy $10 brunch punches. 1072 N. Milwaukee Ave., (773) 772-4322 – Happy hour is available Saturday through Thursday.

North Center

Tavern on Little Fort provides the best of both worlds with the sidewalk patio and beer garden. Come in and enjoy daily specials and stick around to enjoy the spring weather. On Mondays, wraps are $4 and glasses of wine are $5. On Tuesdays, you can get $4 Budweisers and Bud Light tallboys and for $10, you can pair that tallboy with a burger. On Wednesdays, sandwiches are $5, pints of Blue Moon are $4, and buckets of Miller or Coors are $15. On Thursdays, you and your crew can participate in trivia night while enjoying $2 tacos and select $4 and $5 drafts and bottles. Unwind from the work week on Fridays with $5 burgers, $6 Green Line drafts, $4 312 bottles, and $6 Moscow mules. Brunch is served on weekends, along with $3 mimosas and $5 Bloody Marys. 4128 N. Lincoln Ave., (773) 360-1869 – Happy hour is available all day, every day.


BitchBiz: Bitches Who Brunch partners with Pinstripes. While this article was written independently by Bitches Who Brunch, we do receive compensation from the company.


On the weekend, Ana struggles to choose between sweet and savory brunch options. During the week, she helps the hospitality and tourism industries reach millennials online through her digital marketing agency, BLOOM Digital Marketing.

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