The Haute Seeker

The Best Festivals in Chicago: According to The Haute Seeker

Festival season has finally arrived in Chicago! As an avid festival goer, I am ecstatic that many pre-pandemic festivals are back. While some things may have changed with the festivals overall in Chicago such as the price of admission or location. Many things continue to remain the same. Like great food, exposure to local shops, and the spirit of community and cultural exchanges that can only be found in Chicago.

From downtown art festivals to neighborhood street fairs, here is your expert guide to the best summer festivals and events from The Haute Seeker.

Festivals and events are subject to change. Be sure to check times, price of admission, and locations before heading out to one or more of these amazing festivals as well as the venue’s website or social media page for the latest update on COVID-19 protocols and safety measurements. 

Chicago Festivals

Mole de Mayo // Image by Taylor Justin

Puerto Rican People Day Parade. June 11th. Chicago’s annual Puerto Rican People’s Day Parade is a festive celebration of Puerto Rican pride and culture in Chicago. The Parade will be from Division Street and Campbell Street; proceeding west on Division St. through the heart of the Puerto Rican commercial and cultural community- Paseo Boricua in Humboldt Park- culminating on Sacramento and Division. For more parade details, visit the website here. This event is free to attend.

Mole de Mayo. May 27th – 29th . The only outdoor mole cook-off event celebrating Latino culture and Mexican cuisine. For over a decade this festival has kept up with time-honored tradition, local chefs and restaurants will face off and vie for the coveted title of “Best Mole” and “People’s Choice” award. The three-day fest includes an open-air mercado that will be bustling with local merchants, crafters, lucha libre wrestling, and artisans. For more details about this event, visit Mole de

57th Street Art Fair. June 4th – 5th. The Hyde Park-based festival provides a wonderful venue for creators of quality fine art and fine craft to meet with the art-buying public. Whether you are looking for glass, jewelry, leather, photography, printmaking, painting, sculpture, digital arts, wood, ceramics, or fiber — you are sure to find something special at this one-of-a-kind event. For more details, visit the website here.

Hyde Park Summer Fest. June 11th – 12th. Formerly known as Hyde Park Brew Fest, the Hyde Park Summer Fest is quickly becoming a popular music festival on the South Side of Chicago. This year, major hip-hop and R&B artists like Jhene Aiko, Busta Rhymes, BJ the Chicago Kid and more will perform live at the Midway Plaisance in Hyde Park. To purchase tickets and to see a full lineup of artists and more, visit Hyde Park Summer Fest.

Wells Street Art Festival. June 11th – 12th. Experience juried artists from across the country, live music and entertainment, and delicious food—all in the historic Old Town neighborhood. Admission to this event is with a suggested donation. For more event details, visit Wells Street Art Festival.

Gold Coast Art Festival. June 18th – 19th. The award-winning, family-friendly art fair welcomes 200 juried artists from around the country and draws thousands of art enthusiasts from Chicago and beyond, creating an exceptional, shoppable art experience. Admission to this event is $10 and children 12 and under are free which benefits the Chicago Furniture Bank. Find more details on this annual fair by visiting the Gold Coast Art Festival.

Taste of Randolph Street. June 17th – 19th. Head to the West Loop for a major summer festival on Randolph Street this summer in Chicago. This festival brings together the biggest and brightest names in Chicago dining, featuring over 16 restaurants exemplary for delectable menus and irresistibly unique flavors. The festival will also feature a line-up of the nation’s hottest up-and-coming bands and musicians, as well as the biggest names in Chicago house music, performing on two stages and a DJ stage, to entertain guests on their culinary adventure. For more festival details, visit the website here.

Logan Square Arts Festival. June 24th – June 26th. The Logan Square Arts Festival returns this summer after a two-year hiatus. Logan Square’s premier cultural event features two stages of live music, food, drinks, and a renewed focus on creating a one-of-kind experience in one of the most iconic green spaces in the city of Chicago. Tickets to this event are free. For more details, visit Logan Square Arts Festival.

Chicago Food Truck Fest. June 25th – 26th. We have enjoyed some fun years hosting one of America’s top food truck festivals. Experiencing an amazing gathering of mobile chefs preparing a range of culinary creations. All the while bringing together Chicagoans and foodies throughout the country for a peaceful family day to taste and enjoy Chicago eats. Tickets to this event are free. To RSVP and to learn more about this festival, visit the website.

Fiesta del Sol. June 28th – 31st. Check out the largest Latino festival in the Midwest this summer in Chicago. The popular family-friendly Mexican festival is in the heart of one of Chicago’s most attractive communities – Pilsen. This event spans an eight-block space down Cermak Road and features carnival entertainment plus the bright lights of over 100 booths showcasing some of the best tacos, tamales, and tostadas in town. Admission to this event is free or you can purchase a MegaPass for $55 which gives you access to unlimited rides. To learn more details about this event, visit their website.

African/Caribbean International Festival of Life // Image by Taylor Justin

Chosen Few DJs Music Festival & Picnic. July 2nd. Celebrate “House Music” a Chicago original during the 4th of July holiday weekend in Chicago. The Chosen Few DJs Music festival and picnic gather lovers, followers, DJs, dancers, and more to Jackson Park celebrating the love of the popular Chicago-originated genre. Tickets range from $250 – $400. To learn more about this festival and to purchase tickets, visit Chosen Few

African/Caribbean International Festival of Life. July 2nd – 4th. The International Festival of Life. Dedicated to the diverse culture and music primarily from the Caribbean, Africa, Latin America, and the United States. The festival brings people and communities together through music, culture, and the celebration of life. The price of admission varies between $25 – 175. For more festival details visit, the event website.

Silver Room Block Party. July 16th – 17th. One of my favorite annual festivals, the Silver Room Block Party is back for a reimagined experience this summer. The two-day festival will head to the beach and will feature the usual dope musical lineup across multiple stages, but we’ve added local food vendors, a health + wellness area, a design pavilion, beach volleyball, and more. Tickets start at $40 and are available online. To learn more about the event, visit the Silver Room Block

Lollapalooza. July 28th -31st. Music lovers from around the world make their way to Chicago for the annual festival—of the biggest festivals to ever rock the city. With world-class acts, numerous stages, unmatched food experiences, and more Lollapalooza is a major festival that hundreds of thousands attend every year. Tickets for the festival range from $125 – $4,200. For the full lineup of acts, visit the website here. Haute Tip: Splurge and purchase VIP tickets. Why? Clean bathrooms.

Northalsted Market Days. August 6th – 7th. Celebrate the life and community of the historic Boystown/Lakeview in Chicago this summer. Northalsted Market Days is a 1/2 mile long festival featuring that is celebrating a milestone anniversary this year with a weekend-long lineup of live music on 6 stages, 250+ unique vendors, arts, crafts, food and drink, and DJs and dancing, sponsor booths, and more. Admission is a suggested $15 donation that will support local non-profits and community projects. For full details on this event, visit their website here.

Bud Billiken Parade. August 13th. You know it’s almost back-to-school season when The Bud Billiken parade is around the corner! The Bud Billiken® Parade is more than a procession of bands and floats marching down King Drive, it’s a commemoration of our past and a celebration of our future. Every summer since 1929, “The Bud” has united African-Americans throughout the city of Chicago in music, dance, food, and laughter. Admission to this event is free. For more details on this annual parade, visit the website here.

Ruido Fest. August 19th – 21st. The popular festival that celebrates Latin music and culture with internationally headlining acts from all over the Spanish-speaking world. Ruido Fest is an annual multi-day Latin American music festival that takes place annually at Union Park. The tickets range from $99 – $249.00. For more details including the festival lineup, visit the website here.

Chicago Air and Water Show. August 20th – 21st. The Air and Water show features military and civilian flight aerobatics, historic aircraft, simulated water rescues, and parachute teams, the Chicago Air and Water Show is one of the largest and longest-running free admission events of its kind. Admission is free attend this event. Check out the website for more details.

Taste of Greektown. August 26th – 28th. Hellenic pride will take center stage when this acclaimed annual culinary fest on Halsted Street. As most Chicagoans know, this strip of Halsted has been the epicenter of the city’s acclaimed Greek restaurant scene for decades. Quite simply, Taste of Greektown is a romantic weekend celebration for lovers of Mediterranean culture. Check out the full lineup of events and more by visiting the festival’s website.

Annual African Festival of the Arts. September 2nd – 5th. Watch the festival grounds of Chicago’s Washington Park come alive in a simulated African village. Attendees are transported across the Diaspora with interactive engagements, vibrant drumming, museum quality and collectible artifacts. Plus a myriad of colorful and rich handwoven fabric and textile, and other program spaces and interactive spaces.

Hyde Park Jazz Festival. September 24th – 25th. The Hyde Park Jazz Festival is an annual festival that features jazz musicians from around the world. The free event is a wonderful festival to enjoy during the late summer season in Chicago. Admission is free, but a donation of $15 per person is appreciated. For more details, visit the website. Haute Tip: Pack a picnic and listen to the festival in the grassy area of the Midway Plaisance.

Free Summer Long Events in Chicago

Hyde Park Farmers Market featured on The Haute Seeker
Summer Farmers Market // Image vi

Movies in the Park. June 14th – September 3rd. Catch a movie under the Chicago skies this summer at Movies in the Park. Movies are brought to the big screen in neighborhood parks. From classics to major superhero blockbusters. Check out the full lineup by following here. As always, admission is always free.

Farmers’ Markets. May 1st – November 13th. Various markets across Chicago sell fresh seasonal produce, flowers, prepared foods, unique Chicago-made products, and rare finds – at Chicago’s longest-running farmers’ market on Daley Plaza, the historic Maxwell Street Market, and a dozen more community markets in neighborhoods across Chicago. Check out the full list of farmers markets in Chicago here.

Chicago Summer Dance. July 6th – September 17th. Dance to the sounds of 48 different live bands and DJs with steps beforehand at the annual summer event. Free admission. Check out the schedule and choose your favorite night to swing, step, waltz, cha-cha, and more.

Sundays on State Street. July 24th – September 4th. Sundays on State takes over Chicago’s most iconic street, State Street to showcase art, culture, active recreation, food, drinks, shopping and more in the Loop. Join neighbors from every Chicago community and beyond for this free, interactive block party in the heart of Chicago.

Summer Fireworks at Navy Pier. Chicago’s favorite sky spectacle show Wednesday and Saturday nights from Memorial Day weekend through Labor Day weekend. Find a spot anywhere on the pier to take in this dazzling free display. Soundtracks feature dramatic and popular music with some special occasion soundtracks. 

This is just a small amount of the major things to do that Chicago has to offer. Be sure to check out our events calendar for more things to do every day of the week this summer in Chicago.

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