I don’t know about you, but as soon as the temperatures start to rise, I can’t help but get excited for summer in Chicago! The city truly comes alive with an incredible lineup of festivals celebrating music, food, culture, and more. Whether I’m dancing at SummerDance, indulging at Taste of Chicago, or catching my favorite band at Lollapalooza, there’s always something happening…just another reason to love Chicago!
Top Summer Festivals in Chicago for 2025
From neighborhood street festivals to big musical extravaganzas that last for days, Chicago’s 2025 summer festival lineup promises a good time. Mark your calendars, start planning, and let’s make this summer one to remember!
EXPERT-TIP: Chicago’s neighborhood street fairs and festivals are a great time to explore the different areas in the city.
June Festivals in Chicago
Chicago Blues Festival
📍 Location: Ramova Theatre, Jay Pritzker Pavilion, and throughout Millennium Park
🗓️ Dates: June 5-8
Kicking off Chicago’s summer festival season, the Chicago Blues Festival is the largest free blues festival in the world! Expect legendary performances from iconic blues artists and emerging talents. With events spread across multiple venues, there’s no shortage of places to soak in the soulful sounds. This is hands-down my favorite Chicago music festival.
Lincoln Square Greek Fest
📍 Location: St. Demetrios Greek Orthodox Church, Lincoln Square
🗓️ Dates: June 7-9
Get ready for delicious Greek food, traditional music, and plenty of dancing at this community-focused festival. Don’t leave without trying the loukoumades (Greek honey puffs)!
Taste of Chicago (Neighborhood Event: Marquette Park)
📍 Location: Marquette Park
🗓️ Date: June 28
This first of three neighborhood Taste of Chicago events brings local flavors to Marquette Park, showcasing food vendors, entertainment, and family-friendly fun.
July Festivals in Chicago
Chicago Gospel Music Festival
📍 Location: Jay Pritzker Pavilion
🗓️ Dates: July 12
Celebrate the rich history of gospel music in Chicago at this beloved annual festival. Featuring powerhouse performances from local and national artists, the event showcases the genre’s deep-rooted influence on modern music.
Chicago SummerDance
📍 Location: Citywide, including pop-ups and special events
🗓️ Dates: TBA (June–September)
Love to dance? The Chicago SummerDance series brings free outdoor dance lessons, live music, and dance parties to parks and public spaces throughout the city. It’s the perfect way to get moving and enjoy warm summer evenings!
Wicker Park Fest
📍 Location: Milwaukee Ave, Wicker Park
🗓️ Dates: July 26-27
One of the city’s best street festivals, Wicker Park Fest features live indie music, local art vendors, and an incredible selection of neighborhood restaurants serving up everything from gourmet burgers to authentic tacos. Wicker Park is one of my favorite neighborhoods in the city, with so much to do and see.
🍽️ Taste of Chicago (Neighborhood Event: Pullman Park)
📍 Location: Pullman Park
🗓️ Date: July 19
🍕 This Taste of Chicago neighborhood event brings some of the city’s best food to Pullman Park, making it a must-visit for foodies.
.August Festivals in Chicago
Lollapalooza
📍 Location: Grant Park
🗓️ Dates: August 1-4
🎤 Chicago’s biggest music festival, Lollapalooza, takes over Grant Park for four days of non-stop performances from some of the biggest names in music. With multiple stages featuring rock, pop, hip-hop, and electronic acts, plus a vibrant food and art scene, it’s a bucket-list experience for music lovers.
Chicago Air and Water Show
📍 Location: North Avenue Beach & Lakefront
🗓️ Dates: August 16-17
One of the largest free air shows in the U.S., the Chicago Air and Water Show is an adrenaline-fueled spectacle featuring the U.S. Navy Blue Angels, daring aerial stunts, and dramatic water rescues. Whether you’re watching from popular North Avenue Beach, a rooftop, or a boat, this is a summer highlight you don’t want to miss.
🍽️Taste of Chicago (Neighborhood Event: Albany Park)
📍 Location: Albany Park
🗓️ Date: August 9
The final Taste of Chicago neighborhood event takes place in Albany Park, offering diverse flavors and fun entertainment.
Chicago House Music Festival and Conference
📍 Location: Chicago Cultural Center, Millennium Park, Spirit of Music Garden, and Riverwalk
🗓️ Dates: August 22-23
Celebrate Chicago’s legacy as the birthplace of house music with this electrifying festival featuring live DJ sets, panel discussions, and dance parties across the city.
Ribfest Chicago
📍 Location: Lincoln Ave, North Center
🗓️ Dates: August 16-18
Meat lovers rejoice! Ribfest Chicago brings together the city’s best BBQ masters, serving up mouthwatering ribs alongside live music and fun activities for all ages.
Chicago Jazz Festival
📍 Location: Citywide, including the Chicago Cultural Center and Millennium Park
🗓️ Dates: August 28-31
Jazz lovers won’t want to miss this four-day festival featuring world-class performances from renowned jazz artists and up-and-coming musicians.
September & Beyond
Taste of Chicago (Main Event)
📍 Location: Grant Park
🗓️ Dates: September 5-7
The grand finale of Taste of Chicago takes over Grant Park with a massive celebration of the city’s best cuisine, food trucks, and live entertainment.
Windy City Wine Festival
📍 Location: Buckingham Fountain, Grant Park
🗓️ Dates: September 6-7
Enjoy an evening of fine wine tasting, live jazz, and breathtaking views of the Chicago skyline at this elegant event.
West Loop Art Fest
📍 Location: West Loop, along Washington Blvd
🗓️ Dates: September 14-15
A celebration of creativity, this festival showcases artists from across the country, along with interactive exhibits, live murals, and craft beer tastings.
🌍 World Music Festival Chicago
📍 Location: Citywide, including the Chicago Cultural Center
🗓️ Dates: September 26-October 5
🎶 Experience a musical journey around the world at this citywide festival featuring artists from across the globe.
Plan Your Perfect Chicago Summer
No matter your vibe, Chicago’s summer festival season is packed with events for every taste. Whether you’re dancing, eating, or exploring, there’s something exciting happening every weekend!
Stay tuned to LittleChicagoGuide.com for more insider tips on navigating these summer events. Let’s make summer 2025 in Chicago unforgettable!
Pro Tip: Many festivals offer free admission, so all you need is a plan and some comfortable shoes to make the most of them!