Chicago’s Festival Fever: A Guide to the City’s Must-Visit Summer Events

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Maybe it’s our long winters or all-too-short springs, but summertime in the Windy City is one of the best seasons anywhere on the planet. And as one of the country’s premier hotspots for citywide and neighborhood festivals, Chicago knows how to throw a party. From one of the largest music fests in the world to art fairs to food-themed events, there’s always a reason to get out and enjoy summer in Chicago.

Read on for a roundup of @properties Christie’s International Real Estate’s favorite Chicago summer festivals.

Classic: Randolph Street Market – May 25-26, 2024

Image credit: Randolphstreetmarket.com

Named by USA Today as one of the best flea markets in the country for finding vintage gems, Randolph Street Market is a shopper’s paradise in the West Loop. With over 200 outdoor and indoor vendors, it’s also the largest urban antiques market in the country. Need a break from shopping? The fest also offers plenty of live entertainment. This year’s lineup includes several DJs, local bands and on-demand poetry.

Hidden Gem: Chicago Vintage Festival – June 15-16

Image credit: Time Out Chicago

Chicago Vintage Festival is a pop-up vintage and antique flea market taking a tour of Chicago’s neighborhoods this summer. Their next stop is in Bucktown on June 15 and 16. Then they’ll hit Fulton Market, Wrigleyville, Gold Coast and Pilsen. Stay tuned to their Instagram page for exact locations, You can register for free passes to pop-ups on their website and be sure to arrive early – the first 50 people in line get a free tote!

Classic: Lollapalooza – August 1-4, 2024

Image credit: Choosechicago.com

Lolla is hands down the biggest music festival in Chicago, bringing nearly 500,000 attendees to Grant Park every year. What began as a touring festival has transformed into a Chicago staple going on nearly 20 years. Not your ordinary one-genre music fest, Lolla brings dozens of prominent acts from across the music spectrum. This year’s lineup features a typically diverse mix from Hozier and Renee Rapp to SZA and Huddy.

Hidden Gem: Chicago House Music Festival – June 2, 2024

Image credit: Chicago Reader 

Chicago may be best known for innovations like deep dish pizza, but the city has also birthed and transformed several genres of music. One in particular that started here is House, a style of electronic dance music that defined the club scene of the 1980s. We celebrate all things House yearly at the Chicago House Music Festival in Millennium Park. This one-day gathering brings some of the biggest names in the genre, like Ash Lauryn and Anané.

Classic: Chicago Pride Fest – June 22-23, 2024

Image credit: NorthHalsted Business Alliance

Continuing the trend of “Go Big or Go Home,” Chicago Pride Fest is a party on a whole other level. Over 100,000 people come each year to celebrate community and being true to oneself. The center of the action is on Halsted Street between Addison and Grace, with festivities spilling over into nearby restaurants, bars and clubs. The event takes place the week before the annual Pride Parade, so leave some fuel in the tank for the following can’t-miss weekend.

Hidden Gem: Back Lot Bash – June 28-30, 2024

Image credit: NorthHalsted Business Alliance

Further north in Andersonville is the women-focused pride event Back Lot Bash. This celebration occurs on a smaller scale than Pride Fest but still packs a punch with live performances, DJ sets, food and drink. This year, the event celebrates its 20th anniversary and will be held in the parking lot by the Cheetah Gym in the 5200 block of North Clark Street.

Classic: Taste of Chicago – September 6-8, 2024

Image credit: Audacity.com

The Second City is #1 when it comes to food, and nowhere is that more evident than at Taste of Chicago, the largest food festival in the world. The original idea for Taste was conceived by legendary restauranteur Arnie Morton, backed by the equally dynamic cultural affairs guru, Lois Weisberg, and launched during the Jane Byrne administration in 1980. That year, the festival drew 250,000 people. Nowadays, it draws millions. Patrons stroll through Grant Park chomping on Chicago staples like deep dish pizza, Italian beef sandwiches, cheesecake, and don’t forget those giant turkey legs. There’s also live music. It’s a bucket-list Chicago summer activity, and if you haven’t been in a while, it’s worth another visit.

Hidden Gem: Chicago Food Truck Festival – July 20 – 21, 2024

Image credit: thedaleycenter.com

Take a walk on a sunny day in Chicago and you’ll spot plenty of food trucks parked around the city. But with the Chicago Food Truck Festival, you can savor the flavors in one spot. Located in the South Loop near McCormick Place, this year’s fest is themed “The Summer of the Daisy” and will feature live music and a collaboration with the Chicago Margarita Festival (Margarita is Spanish for ‘daisy’). Admission is free, but if you want to beat the crowds, VIP access is only $10, and it includes a drink ticket!

Classic: World Music Festival Chicago – September 20-29, 2024

Image credit: choosechicago.com

The World Music Festival is a perfect way to close out the summer season. This festival brings over 30 artists from 22 countries to venues around Chicago including the Chicago Cultural Center, Millennium Park, and Navy Pier. You can hear everything at the World Music Festival — from Senegalese Afro-pop to Moroccan-French psychedelic rock. The best part? This is one of the few large music festivals in Chicago that offers free admission.

Hidden Gem: Sueños – May 25-26, 2024

Image credit: Secret Chicago

Months before Lolla lights up the night in Grant Park, Sueños brings together fans of all kinds of Latin music. As one of the newest music festivals in Chicago, Sueños has over two dozen artists and Latin cultural activities for everyone to enjoy. You can kick off the summer festival season with artists like Rauw Alejandro and Bad Gyal in the bustle of downtown.

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