“The Strokes” Cocktail Special at aliveOne

  • Thursday, August 1 through Sunday, August 4
  • $5 to $8 drink specials

Guests who stop at aliveOne during Lollapalooza weekend will enjoy their signature “The Strokes” cocktail for $8 each. The drink features Crown Royal, Yellow Chartreuse, lemon juice and Regan’s orange bitters. Additional specials will include $5 Half Acre Tuna beers and a daily half-price happy hour from 5 p.m. to 7 p.m.

“Frozen Lolla Lemonade” at Castaways

  • Thursday, August 1 through Sunday, August 4
  • $9 drink special

Fest-goers can cool off at Castaways on North Avenue beach during Lollapalooza weekend with a “Frozen Lolla Lemonade” featuring Absolut Vodka and lemonade for $9 each. Castaways serves lunch and dinner every day from 11 a.m. to 11 p.m. and drinks from noon to 11 p.m. Menu items include beachside fare like fresh salads, wraps, sandwiches, quesadillas and more.

Lollapalooza Cocktail at Easy Bar

  • Thursday, August 1 through Sunday, August 4
  • $8 drink special

In celebration of Lollapalooza 2019, Easy Bar will offer The Humdinger cocktail for $8 each from Thursday, August 1 through Sunday, August 4. The cocktail, named after the history behind the word “lollapalooza” according to the Merriam Webster Dictionary, features Rittenhouse Rye, crème de cassis, orange, simple, Angostura bitters and a prosecco float.

Lollapalooza Shot Special and Late Night Bites at Estelle’s

  • Thursday, August 1 through Sunday, August 4
  • $5 shot special 

In celebration of 28 years of Lollapalooza this August, Estelle’s will feature a $5 Mystery Lolla Shot available for the duration of the fest. For guests looking for a spot to hang late-night with friends and refuel, Estelle’s kitchen is open all night with options like house-made burgers and sandwiches, loaded fries, fried pickle spears, nachos and more. Menu specials include $5 quesadillas on Thursday and a $10 loaded nacho burger on Sunday. Estelle’s is open until 4 a.m. Thursday, Friday and Sunday and 5 a.m. on Saturday.

Lolla Pregame Happy Hour at Parlay

  • Thursday, August 1 & Friday, August 2
  • $2 to $20

Fest-goers headed to Lollapalooza on Thursday or Friday night are invited to enjoy a Lolla pregame happy hour at Parlay from 4 p.m. to 7 p.m. which includes $7 Don Julio 1942 and Clase Azul shots, $5 Stolen Rum and Stolen Whiskey Cocktails, $5 White Claw, $5 glasses of select wine and $10 pizzas.

Post Lolla Late Night Menu at Play 

  • Thursday, August 1 through Sunday, August 4 from 10 p.m. to close
  • $8 to $45 

Lollapalooza fest-goers that are looking to refuel and keep the party going post Lolla can enjoy a late night food menu from Executive Chef Melva Jarvis at Play Kitchen & Cocktails located in Chicago’s Gold Coast. Available from 10 p.m. to close, the menu features shareable items like Brisket Sliders, Margherita Flatbread, Southwest Roll-Ups, and Play’s signature 24-Karat Gold Wings, house smoked jumbo wings tossed in 24K gold bourbon BBQ sauce with 24K gold flakes and served with ranch or blue cheese sauce. Play is open until 4 a.m. Thursday, Friday and Sunday and until 5 a.m. on Saturday.

“Rhubarbarellapalooza” at Remedy 

  • Thursday, August 1 through Sunday, August 4
  • $8 “Rhubarbarellapalooza” cocktail

In recognition of Lollapalooza, Remedy in Bucktown will mix up a “Rhubarbarellapalooza” cocktail made with Aviation gin, Aperol, lemon juice and rhubarb bitters for $8 each. Open until 4 a.m. (5 a.m. on Saturdays), Remedy will keep the party going after Lollapalooza.

Lollapalooza Fest-Goer Discount at The Owl

  • Thursday, August 1 through Sunday, August 4
  • $1 off beer special

Lollapalooza fest-goers who stop by The Owl in Logan Square after the festival will enjoy $1 off Miller High Life, Miller Light and Budweiser bottles when they show their wristband. For guests looking for a great after party spot, The Owl is open until 4 a.m. Thursday, Friday and Sunday and 5 a.m. on Saturday.

Z Bar Brunch Jess Paro 2
Z Bar Brunch (Courtesy of Jess Paro)

Z Bar

Kick your Lollapalooza weekend off at Z Bar, the Peninsula Chicago Hotel’s rooftop terrace overlooking Michigan Ave, as they turn their weekend brunch into Pre-Lolla Brunch 11:30-3pm Saturday and Sunday, August 3 & 4. Sip on specialty brunch cocktails that pay homage to this year’s headliners, including the the “Ariana Grande,” a boozy frozen slushy made with rum, coffee, Amaretto and cinnamon; the “Twenty One Pilots,” an Aviation-style spritz with floral and citrus notes; and “The Chainsmokers,” a smoky Bloody Mary made with mezcal and burnt sage. DJ Akib and DJ Cloudstomper will play Saturday and Sunday respectively from noon to 3pm, to get festival-goers in the mood before they head to Grant Park. 

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Source: http://www.chicagofoodmagazine.com/news/lollapalooza-dining-drinking-specials-in-chicago