If you’re heading to Lollapalooza this weekend, you should already have your vacation rental booked, your packing essentials in mind, and your wristband activated, but have you done your homework on the best spots to hit while you’re there? With Chicago positioned in the #1 slot for the best food cities in the United States, you might as well make the most of your trip and scope out a few amazing bars and eateries in the Windy City. 

The four day music festival will house nine different stages in Grant Park, located down the street from the giant reflective bean known as Cloud Gate. To your advantage, there’s lots to explore around the local area known as the Loop


Exploring The Loop: Where to Eat

To make your life easier, we’ve rounded up the best places to eat, all within walking distance of the festival. Starting with Lou Malnati’s Pizzeria on South State Street, you already know we had to start with Chicago’s finest: deep dish pizza. Only ten minutes away from Grant Park and rated by Zagat as “a true Chicago classic,” you won’t have to go out of your way to get your hands on a hearty serving of rich tomato sauce and melted cheese, freshly baked on top of Lou’s signature buttercrust. 


If you’re in a rush and want to grab a quick bite before the festival, try a pressed Cuban sandwich from Cafecito. Their extensive menu may get a little overwhelming because everything sounds so delicious, but for starters, try the Mar y Tierra sandwich, made up of spanish chorizo, shrimp, and citrus garlic aioli. Or, if you’re in the mood to try Cafecito’s take on a traditional Cuban dish, go for the Ropa Vieja, consisting of shredded steak in a tomato sauce.

You’ll find a few Cafecito coffee houses scattered around the city, but the closest one to Lollapalooza is the branch on East Congress Parkway, less than ten minutes outside of the venue.


To get a taste of several local vendors under one roof, take a 20 minute walk north from the festival grounds to Revival Food Hall. Right off the bat, Antique Taco’s chorizo chili cheese curds and crab flautas are calling our name. But if you’re in a carnivorous mood, dig into the savory smoked meats at Smoque BBQ. You get the option of sliced brisket versus chopped brisket, or you can also try their homemade jalapeno cheddar sausage, among other meats on the menu.


One other dish at Revival that catches our eye is the Furious Ramen from Furious Spoon, made with fresh noodles, house-made chashu pork, and topped with tasty chicken and pork dumplings. With so many different cuisines to choose from, this food hall is a foodie’s paradise.

We also can’t forget to mention a true local favorite: Cindy’s Rooftop, just a 15 minute stroll from Lollapalooza. This place is great for both food and drinks, with a welcoming ambiance on a rooftop overlooking Lake Michigan and Millennium Park. Keep in mind that if you’re visiting during Lollapalooza weekend, they will run regular business hours everyday except for dinner on Sunday, August 4th due to a private event. 

Happy Hour Around The Loop

Onto the fun part – happy hour! There are tons of places to get your pregame on while soaking in Chicago culture at one of the Loop’s trendy bars and restaurants. Check out a few of your options below.

#1: Acanto on South Michigan Street

Starting off with Acanto, this Italian restaurant is a lovely place for happy hour, right across the street from Millennium Park. The establishment’s building on 18 South Michigan Avenue is one of three Gage Group Buildings, now a historic landmark due to its architectural significance in the 20th century.

  • Happy Hour Times: Monday Friday from 2:30pm – 5:30pm
  • Distance From Lollapalooza: 6 minute drive, 15 minute walk
  • Best Happy Hour Deals: $4 bruschetta, $5 beer, and $8 glasses of wine


#2: AceBounce on North Clark Street

Next up is AceBounce, an exciting social club with ping pong, beer pong and wonderball. Their latest cocktail menu is an ode to classic ‘90s sitcoms such as the Fresh Prince of Bel Air, Friends, and Full House. Be sure to book directly on their website if you and your friends plan on playing a round of games!

  • Happy Hour Times: Monday Thursday from 4:00pm – 7:00pm, and Friday from 12:00pm – 7:00pm
  • Distance From Lollapalooza: 10 minute drive, 30 minute walk
  • Best Happy Hour Deals: $5 beers, vodka cocktails, and glasses of wine


#3: Land & Lake Kitchen on East Wacker Drive

Lastly, you can visit Land & Lake Kitchen featuring indoor and outdoor seating close to the Chicago River. Aside from happy hour, they also host bottomless mimosa brunch from 11:00am – 3:00pm on Saturdays and Sundays.

  • Happy Hour Times: Monday Friday from 4:00pm – 7:00pm
  • Distance From Lollapalooza: 10 minute drive, 25 minute walk
  • Best Happy Hour Deals: $4 beers, $5.50 glasses of house wine, and $6.50 cocktails


Unwinding After the Festival

Staying a day or two after the festival? You got the right idea. 

Take some time to explore the Windy City’s most in demand sites. If you haven’t done so already, spend an afternoon in Millennium Park and snap a photo at the famous Cloud Gate. From there, you can also walk 20 minutes inland to the Willis Tower and test your fear of heights on the Skydeck, 103 floors up!


Then, follow the Chicago River north until you hit the Chicago Riverwalk. You can walk along the pedestrian path, parallel to the river, all the way until you reach City Winery right by the water. It’s the perfect place to end your afternoon with a refreshing drink in hand.


Your Go-To Lollapalooza 2019 Playlist

Lollapalooza’s lineup will be packed with incredible performances each day as any four day festival should but we put together a playlist of some of our favorite songs by this year’s lineup.  Get hyped up while listening to it on your way to Chicago, or play it in your vacation rental while pregaming with your best buds. All that matters is that you have a great time while listening!


In the mood for a spontaneous getaway to Lollapalooza 2019? VacationRenter’s got you covered with the perfect rental.