Festivals in Chicago: Guide to Best Summer Events 2025

There's never a dull moment with all these summer festivals in Chicago!

Summer in Chicago means one thing: festivals. Every weekend there are festivals featuring music, food, shopping, and more fun things to do.

From neighborhood street festivals to epic multi-day extravaganzas, these outdoor parties make you forget all about the snow and cold of winter in Chicago.

To help your planning, here are some of the best summer festivals in Chicago.

a large group of people sitting outside a concert hall

Essential Tips for Festival-Goers

  • Plan Ahead: With a packed schedule, be sure to mark your calendar with must-attend events.
  • Arrive Early: Beat the crowds to secure the best spots and explore the grounds comfortably.
  • Dress Smart: Prepare for hot weather but be ready for sudden changes. Essentials include sunscreen, comfortable clothes, and a rain jacket.
  • Stay Hydrated: Keep a water bottle handy, especially during outdoor events.
  • Bring Cash: Some vendors may not accept cards. Having cash can make purchases smoother.
  • Use Public Transportation: Chicago’s transit system is a great way to get around, especially to avoid parking hassles.
  • Secure Your Belongings: Keep your items close in crowded places to avoid loss or theft.

Recurring Summer Festivals in Chicago

Concert in Millennium Park, one of the many festivals in Chicago

Millennium Park Summer Workouts

May 17 – August 30, Millennium Park

Free morning fitness sessions on Saturdays, including Yoga, Pilates, Zumba, and Cardio Kickboxing on the Great Lawn.

Chicago Farmers Markets

May 15 – October 31, various neighborhoods

Farmers markets across the city, offering fresh local produce, flowers, and artisanal goods. Daley Plaza market opens May 15.

May 24 – August 30, Navy Pier

Fireworks every Wednesday (9 p.m.) and Saturday (10 p.m.) over Lake Michigan, paired with music.

Jazzin’ at the Shedd

May 28 – August 27, Wednesdays, Shedd Aquarium

Live jazz, skyline views, and aquarium access every Wednesday night. Requires a ticket.

Tuesdays on the Terrace

June 24 – August 26, Museum of Contemporary Art Chicago

Free jazz concerts on the MCA’s garden terrace, featuring local and national artists.

Grant Park Music Festival

June 11 – August 16, Jay Pritzker Pavilion, Millennium Park

Free outdoor classical concerts featuring the Grant Park Orchestra and Chorus, most Wednesdays, Fridays, and Saturdays.

Millennium Park Summer Music Series

June 26 – August 7, Millennium Park

Free concerts Mondays and Thursdays at the Jay Pritzker Pavilion, spotlighting national and local artists in a wide range of genres.

Millennium Park Summer Film Series

July 1 – August 19, Millennium Park

Free movies on the big screen at Jay Pritzker Pavilion every Tuesday night.

Chicago SummerDance

August 7 – 23, Spirit of Music Garden (601 S Michigan Ave) and pop-ups citywide

Free dance lessons and live music, Thursdays through Saturdays. Special pop-ups throughout the city.

Sundays on State

September 7 & October 5, State Street (Loop)

Chicago’s iconic street turns into a pedestrian-only block party with art, music, food, and pop-up performances.

June Festivals in Chicago

Do Division Street Fest

May 30 – June 1, Division St between Damen & Leavitt, Wicker Park

Three days of live indie music, food, local vendors, and a family fun zone.

Windy City Hot Dog Fest

May 31 – June 1, 4000 N Milwaukee Ave, Portage Park

Vendors compete to be crowned best hot dog in Chicago. Includes music and kids’ activities.

Chicago Blues Festival

June 5–8, Millennium Park & city venues

The nation’s largest free blues festival. Top names perform in Millennium Park and clubs citywide.

Puerto Rican Festival & Parade

June 12-15, Humboldt Park

Music, authentic food, carnival rides, and the city’s biggest parade celebrating Puerto Rican culture.

Andersonville Midsommarfest

June 13 – 15, Clark St between Foster & Gregory

A Swedish-inspired street festival with international food, craft vendors, family activities, and music on five stages.

Old Town Art Fair

June 14–15, Old Town Triangle Historic District, Old Town

One of the country’s best art fairs—more than 200 juried artists, garden walks, music, and food court.

Taste of Randolph

June 13 – 15, Randolph St between Peoria & Racine, West Loop

Sample signature dishes from West Loop’s top restaurants and enjoy a stellar live music lineup.

Chicago Pride Fest

June 21–22, Northalsted (Boystown, Halsted St between Addison & Grace)

A lively celebration of LGBTQ+ pride with music, food, drag shows, and community resources.

Craft Brews at Lincoln Park Zoo

June 28, Lincoln Park Zoo

Sample more than 100 craft beers in the after-hours zoo setting, with music, food trucks, and carousel rides. (21+ event, ticketed)

Chicago Festivals in July

NASCAR Chicago Street Race Weekend

July 5–6, Grant Park and downtown streets

Watch professional NASCAR drivers race through the heart of Chicago. Weekend includes a music festival. (Ticketed)

Windy City Smokeout

July 10–13, United Center parking lot, Near West Side

Four days of country music’s top acts, BBQ from pitmasters around the nation, and craft beer. (Ticketed)

Square Roots Festival

July 11 – 13, Lincoln Square

Folk and roots music, regional craft beers, food, and family activities.

Chosen Few Picnic & Festival

July 12, Jackson Park

World-renowned DJs celebrate Chicago’s house music legacy with thousands of fans in a giant outdoor dance party.

Tacos y Tamales Festival

July 18–20, 16th & Peoria, Pilsen

Traditional Mexican food, art, and music in the heart of Pilsen.

Disability Pride Parade

July 26, 400 S Plymouth, South Loop

A parade and celebration for disability awareness, pride, and inclusion.

Wicker Park Fest

July 25–27, Milwaukee Ave between North & Ashland

A neighborhood music festival known for top indie bands and a creative vendor marketplace.

Chinatown Summer Fair

July 26 – 27, Wentworth Ave & Chinatown Square

Lion dances, martial arts, food, music, and kids’ activities in Chicago’s vibrant Chinatown.

August Chicago Festivals

Lollapalooza

July 31 – August 3, Grant Park

Four-day music festival featuring top acts across genres and emerging artists on multiple stages.

Bud Billiken Parade & Picnic

August 9, King Drive, Bronzeville

The nation’s largest African American parade and back-to-school celebration.

Northalsted Market Days

August 8–10, Northalsted, Halsted St from Belmont to Addison

Two-day street fest with live music on five stages, food, vendors, and a lively crowd.

Broadway in Chicago Summer Concert

August 11, Millennium Park, Jay Pritzker Pavilion

Stars from major shows perform Broadway numbers on stage. Free.

Chicago Air and Water Show

August 16–17, North Avenue Beach and Lakefront

Jaw-dropping aerial acrobatics and military aircraft, plus water stunts. Free and visible along the lakefront.

Chicago Jazz Festival

August 28 – 31, Millennium Park and citywide

A Labor Day tradition, this free festival presents local and international jazz on multiple stages.

September Festivals in Chicago

Taste of Chicago

September 5–7, Grant Park

Sample dishes from dozens of Chicago’s best restaurants and food trucks, with free music on multiple stages.

German-American Oktoberfest

September 5–7, Lincoln Square

Traditional music, beer, food, and a lively parade in the city’s historic German neighborhood.

Retro on Roscoe

September 5 – 7, Roscoe Village

Live music, classic cars, family fun, and vintage vendors.

Lyric Opera’s Sunday in the Park

September 7, Millennium Park

Enjoy performances by Lyric Opera artists in a casual outdoor setting.

Riot Fest

September 19–21, Douglass Park

National punk, rock, and hip-hop acts plus carnival rides and food.

Hyde Park Jazz Festival

September 27–28, venues across Hyde Park

Concerts in parks, churches, and on the Midway Plaisance, featuring the best of Chicago and world jazz.

These fests barely scratch the surface of summer fun in Chicago. For more events, check out our Chicago events calendar.