Festival season has officially arrived in Chicago, and I couldn’t be more excited!
As an avid festival-goer, I know there is nothing like strolling through Chicago neighborhood festivals and outdoor celebrations. While some things continue to evolve for many of these annual festivals(rising ticket prices, new locations, dates, etc), the spirit and energy remain the same: great food, local businesses, and cultural experiences you won’t find anywhere else.
From downtown art fairs to community-driven celebrations in historic neighborhoods, this list features my favorite summer festivals in Chicago, many of which I’ve attended year after year.
See the full list of favorites and share yours in the comments below!
Top Favorite Summer Chicago Festivals
1. Mole de Mayo | Pilsen
One of my favorite neighborhood festivals! This outdoor celebration of Mexican culture features a mole cook-off with local chefs competing for titles like “Best Mole” and “People’s Choice.” You’ll also find lucha libre wrestling, open-air markets, and vibrant community energy in Pilsen.
2. Puerto Rican Fest | Humboldt Park
Chicago’s annual Puerto Rican People’s Day Parade is a festive celebration of Puerto Rican pride and culture in Chicago. From dancing to live music to pride-filled floats, this parade is a true celebration of culture and heritage. Admission to this family-friendly four-day festival ranges between $15 and $50.
3. 57th Street Art Fair | Hyde Park
A South Side staple for art lovers. This free art fair in Chicago brings together top-tier creators across mediums like glass, photography, painting, fiber art, and more. It’s a perfect weekend for discovering one-of-a-kind pieces and supporting artists directly.
4. Ribfest | NorthCenter
Sample and sip on delicious ribs and whiskey at the annual ribs fest in Chicago. Ribfest Chicago takes place every summer in the Northcenter neighborhood! This Northcenter neighborhood staple brings the smoke, the sauce, and the sips with mouthwatering ribs, whiskey tastings, and live music all weekend long.
5. Gold Coast Art Festival | The Loop
The award-winning, family-friendly art fair welcomes 250 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 $15, with $2 from each sale benefitting WINGS Program, Inc. Tickets are required for admission. Children 12 and under are admitted free.
6. Taste of Randolph | West Loop
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 neighborhood restaurants. 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.
7. Logan Square Arts Festival | Logan Square
(Postponed until 2026)The Logan Square Arts Festival is a three-day neighborhood festival in Logan Square. This premier cultural event features two stages of live music, food, drinks, and a renewed focus on creating a one-of-a-kind experience in one of the most iconic green spaces in the city of Chicago.
8. Chicago Food Truck Festival | South Loop
One of the best ways to sample food from all over the city (without committing to just one menu). This fest brings together dozens of Chicago’s best mobile kitchens, from soul food to empanadas.
9. Fiesta Del Sol | Pilsen
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.
10. Chosen Few Picnic and Festival | South Shore
A true Chicago original, the Chosen Few DJs Music Festival & Picnic is a soulful celebration of the genre our city helped create: house music. Every summer, Jackson Park transforms into a high-energy reunion of DJs, dancers, day-one fans, and newcomers alike enjoying the sounds of Chicago’s rich musical legacy.
11. African/Caribbean International Festival of Life | Woodlawn
The International Festival of Life is all about good vibes, global sounds, and community spirit, celebrating cultures from the Caribbean, Africa, Latin America, and right here in the U.S. From the live music to the incredible vendors, the whole space felt like a true celebration of culture. And the food? Unreal.
12. Lollapalooza | The Loop
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
13. Northalsted Market Days® | Northhalsted
Celebrate the 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.
14. Taste of Greektown | Greektown
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 weekend celebration for all things Mediterranean in Chicago.
15. Hyde Park Jazz Festival | Hyde Park
The Hyde Park Jazz Festival is a annual Chicago 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.
16. Windy City Smokeout | West Loop
Windy City Smokeout is a high-energy country music and BBQ festival held outside Chicago’s United Center, featuring top-tier pitmasters from around the country and big-name headliners. Even if you’re not into country music, the lively crowd and incredible food make it a standout summer experience worth attending.
What are the Best Festivals in Chicago? Here are My Final Thoughts
I’ve danced through neighborhood street fests, indulged at foodie gatherings, and wandered art fairs that rival global scenes, all right here in Chicago.
These picks are just a handful of the festivals I’ve come to love over the years, but trust me, there are so many more out there worth exploring.
These are the summer staples I look forward to every year, and I hope they’ll become part of your summer favorites too.
4 responses to “Festival Season Chicago: Here Are My Top 16 Favorites”
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