CHICAGO, IL — APRIL 15, 2025 — As temperatures rise, so does the energy in Chicago, a city that transforms each summer into a patchwork of festivals celebrating everything from house music and jazz to drag shows, barbecue, and cultural heritage. The summer lineup for 2025 is a reminder of why the city is known as a hub for outdoor celebration — a place where neighborhoods take center stage, global performers share space with local legends, and the streets themselves become part of the show.

Here’s a look at some of the season’s most anticipated events:

Pride, Pop, and Drag in Northalsted

June 21–22, 2025
Chicago Pride Fest kicks off the season with a weekend of community and celebration in the city’s historic LGBTQ+ neighborhood of Northalsted. Drawing over 100,000 attendees each year, the fest features three stages of live performances, more than 100 local vendors, food stalls, drag shows, dance troupes, and the crowd-favorite high-heel race. This year’s lineup includes Natasha Bedingfield, JoJo Siwa, Sapphira Cristál, Bob the Drag Queen, and Amber Riley.

Evenings on Argyle

Thursdays, July 3–August 28
On Chicago’s first shared street — a pedestrian-prioritized corridor in Uptown — the Argyle Night Market brings together Asian cuisine, live music, and cultural performances every Thursday night. Organized by Uptown United since 2013, the event is as much about community pride as it is about the food.

Barbecue Meets Country at Windy City Smokeout

July 10–13
Held outside the United Center, the Windy City Smokeout returns for its 12th year with a packed weekend of music and meat. Headliners include Kane Brown, Old Dominion, Jon Pardi, Bailey Zimmerman, and Megan Moroney. Festivalgoers can also enjoy a Bacon Bar and a build-your-own Bloody Mary station at the bottomless BBQ brunch on Sunday, July 13.

Celebrating the Far East in Chinatown

July 26–27
One of Chicago’s most vibrant cultural events, the Chinatown Summer Fair draws more than 50,000 visitors to the neighborhood for two days of music, art, and cuisine. The fair kicks off with a traditional lion dance and features kung fu demonstrations, performances, food stalls, and a bustling street market.

Lollapalooza Returns to Grant Park

July 31–August 3
The city’s biggest music festival brings more than 170 acts to nine stages in Grant Park. This year’s headliners include Olivia Rodrigo, Tyler, the Creator, Sabrina Carpenter, Luke Combs, Rüfüs du Sol, A$AP Rocky, Gracie Abrams, and Doechii. With a mix of mainstream and indie artists, Lollapalooza continues to be a high point of the summer calendar.

Sky-High Spectacle on the Lakefront

August 16–17
Dating back to 1959, the Chicago Air and Water Show is the largest free event of its kind in the United States. More than one million spectators line the Lake Michigan shoreline to witness aerial acrobatics and watercraft demonstrations in a celebration of engineering, daring, and summer tradition.

From House to Jazz, a Homegrown Soundtrack

August 22–31
Chicago closes out summer with two genre-spanning festivals. First, the Chicago House Music Festival and Conference returns to Millennium Park (August 22–23), celebrating the genre born in Chicago’s underground clubs. Then the Chicago Jazz Festival (August 28–31) offers a Labor Day weekend of free programming featuring both international stars and local legends, with performances at the Chicago Cultural Center and Millennium Park.

Whether it’s a late-night set in Grant Park or dumplings on a Thursday night in Uptown, Chicago’s summer festival season offers something for everyone — and every neighborhood. For a full guide to the city’s summer festivals, visit choosechicago.com.