Chicago: Lollapalooza Weekend

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Advisor - Meghan Irle
Curated By

Meghan Irle

  • Boutique Travel

  • City Travel

  • Food & Wine

  • Arts & Culture

  • Chicago

  • High-end

  • Summer

  • Downtown

  • Shopping

  • Architecture

Sky touching buildings in Chicago
Curator’s statement

Chicago is a magical city, especially in the summertime. Attending Lollapalooza is a whole other beast. People travel from all over the world to attend the acclaimed festival which is located in Grant Park, AKA, the heart of the downtown. It is crucial that you plan your trip accordingly so you can get the best of the city while enjoying the art and culture of the festival.

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Where to stay in Chicago

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Things to do in Chicago

2 high rise buildings in front of each other

Oak Street Beach - One of the best beaches in Chicago, this beach is in the Gold Coast. Not only does it have volleyball, restaurants and bars, but it has a great view of the lake's yacht life, the Playpen. Pro tip: Watch the sunrise over Lake Michigan early morning.

John Hancock Observatory - Grab a cocktail and snack on the observatory floor where you can get a 360-view of the city and the lake.

Navy Pier - You can spend hours in Navy Pier. Between the copious amounts of food options, the Ferris wheel, the yacht charters and the botanic gardens, you will run out of time before you run out of things to do.

Millennium Park - This park is located right next to the festival! Visit the bean, a Chicago classic architectural structure or join an outdoor workout/yoga sessions before you boogie all day at Lolla.

Sears Tower - Now known as the Willis Tower, this iconic building used to be the tallest in the world! Go for the history, stay for the views.

Museum Campus - The campus is made up of three buildings, the Shedd Aquarium, the Field Museum (natural history) and the Adler Planetarium. You can buy a museum pass to see these places as well as several others throughout Chicago.

Magnificent Mile - Known for it's high end shopping, the Mag Mile is where you go to get your shopping fix. You are guaranteed to find a last minute festival fit in one of the many shops.

Wrigleyville - Have some extra time? Journey north by Uber or Red Line (train) and experience the place home to the Chicago Cubs. Even on non-game days, this area of the city is always lively. Looking for somewhere to go after the festival ends? Wrigleyville's nightlife is far enough removed that you can leave the Lolla crowd behind.

Places to eat & drink in Chicago

People sitting in an outdoor restaurant and buildings at a distance


Cindy's Rooftop - This solarium style restaurant amazing views of the festival grounds, but make reservations well in advance.

Beatrix - Located in the West Loop, this brunch spot offers up healthy and delicious food.

Cafecito - Close to Grant Park, this coffeehouse specializes in Cuban food and has a ton of Vegan options. This is a great place to grab a quick bite.

3 Arts Club Café - Come for the atmosphere and stay for the food. This garden courtyard restaurant is located at the Restoration Hardware in the Gold Coast.

Freemont - On the main floor you can grab brunch with your besties. Head to the second floor and you are transported to a brunch club with spinning DJs. Reservations are advised.


Radius - A ten minute drive from Grant Park, this newer music venue hosts a slew of DJs throughout the weekend. Buy tickets in advance.

House of Blues - Many Lolla artists hold second shows at this music venue which is designed in a classic Chicago architecture style.

Tao - Asian restaurant by day and club by night, you can find DJs like Steve Aoki mixing here after the festival ends. Buy your tickets well in advance and look into bottle service to ensure you have a space to rest.

Cerise - Situated on top of the Virgin Hotel, this swanky little rooftop bar has eclectic cocktails and features some great DJs.

Brando's Speakeasy - A staple for karaoke and cocktails, conveniently located right near the festival grounds.

Need to Know

For more travel tips, check out Fora Advisor Olivia Thomas’s guide on Exploring Chicago's West Side.

Advisor - Meghan Irle

Travel Advisor

Meghan Irle

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This guide is part of our ongoing series on travel to Chicago.