Festival Season in the Windy City
Celebrate Chicago’s world-renowned festivals! The culture, food, music and history throughout our city by the lake all conveniently located near the Kimpton Gray Hotel. Check out just a few of the event highlights below.

Sueños Chicago
Get to Grant Park this May to experience all-new multi-day Latin music festival, Sueños. World-class production and a curated experience that will leave you with festival memories to last forever.
May 24-25, 2025

Chicago Blues Festival
The largest free blues festival in the world, the Chicago Blues Festival treats fans to three days of live music across four stages citywide and in Millennium Park. The blues capital of the world includes alumni like Ray Charles, B.B. King, Bonnie Raitt, Bo Diddley, Buddy Guy, Koko Taylor, Shemekia Copeland, and Gary Clark Jr.
June 5-8, 2025

Chicago Pride Fest
Chicago Pride Fest® returns June 21–22, 2025, for a two-day celebration of LGBTQ+ life, culture, and community in Chicago’s iconic Northalsted neighborhood. The 24th annual fest features live music across three stages, drag shows, a Youth Pride Space, dance performances, the Proud Pet Parade, and over 150 local food and merchandise vendors. A $15 suggested donation supports performers, workers, and local non-profits, including the Chicago Pride Crosswalks. Held the weekend before the Chicago Pride Parade, Pride Fest is a vibrant kickoff to Pride Week in the city.
June 21-22, 2025

Lollapalooza
Lollapalooza is a four-day music festival that takes over historic Grant Park in Downtown Chicago, alongside the beautiful Chicago skyline and the shores of Lake Michigan.
July 31-Aug 3, 2025

Windy City Smokeout
Chicago’s country music, BBQ & beer festival held outside the iconic United Center. Get four-day tickets to see Bailey Zimmerman, Old Dominion, Kane Brown, Megan Moroney & more!
July 10-13, 2025