Chicago Pride

Pride, grilled cheese, vintage finds, and star-studded performances: Festivals in Chicago this weekend

Whether you’re looking for delicious foods, performances from big-name artists, art, or an epic celebration of Pride Month you can’t be bored with this weekend’s activities

Pride Fest
North Halsted Business Alliance

Chicago has a summer packed full of food festivals, live music, and art shows -- and this weekend will see some major events and neighborhood staples taking place.

Whether you’re looking for delicious foods, performances from big-name artists, art, or an epic celebration of Pride Month you can’t be bored with this weekend’s activities.

Here's a look at what's happening in the city from Friday through Sunday:

Chicago Pride Fest

When: June 22 and 23

Where: Northalsted on Halsted Street from Addison to Grace Street  

What: A street festival celebrating LGBTQ+ life, culture, and community the weekend before the annual pride parade. The event features three main stages for live music, plus a drag performance and food and merchandise vendors. Headliners include Jojo Siwa and Natasha Bedingfield, with performances from many other artists. See more about Pride Fest here.

Vegandale

When: June 22 and 23

Where: Grant Park

What: A festival featuring vegan vendors, free vegan food samples, drinks, and art. Also includes performances from headlines 2Chainz, Saweetie, NLE Choppa, and more.

Magnificent Mile Art Festival

When: June 22 and 23

Where: 875 N. Michigan Ave.

What: A combination of over 50 artists coming together to showcase paintings, photography, glass art, and more. The festival is free to the public and stretches along the magnificent mile, allowing attendees to observe the art while walking one of the most famous streets in the city.

Andersonville Vintage Market

When: June 23

Where: 1500 W. Catalpa, between Clark and Ashland

What: A vintage extravaganza with merchandise from over 30 different vendors. This is one of four of the market’s appearances this summer, with one every month from now through September. See more details here.

Grilled Cheese Fest

When: June 22

Where: 1367 N. Milwaukee Ave.

What: Back by popular demand, Grilled Cheese Fest is a celebration of one of America’s favorite foods, featuring vendors from all over with variations on the classic sandwich. The festival also includes bottomless tomato soup, and activities such as a grilled cheese eating contest. More information available here.

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