Chicago Street Fests

Entries

• 1. Mayfest

  (Lincoln Park, May 15-17, 2026) Located in the heart of Lincoln Park, this vibrant destination offers a rich cultural scene, featuring trendy boutiques, renowned restaurants, and stunning historic architecture. A favorite among both locals and visitors, it perfectly blends charm and energy.

• 2. Mayfestiversary

  (Ravenswood, May 22-24) Mayfestiversary is hosted by two breweries in the Ravenswood area, they have great beer (two breweries), great music, and great food options.

• 3. Belmont-Sheffield Music Fest

  (Lakeview, May 22-24, 2026) Summer starts here! Get ready for an epic kickoff to the season as the Belmont-Sheffield Music Fest returns for its 41st year, taking over the heart of Lakeview starting Friday evening of Memorial Day Weekend. Just steps from the Belmont El station, this iconic street festival is the ultimate celebration of music, community, and summertime vibes.

• 4. Do Division Street Fest

  (West Town, May 29–31, 2026) The music and retailers are diverse, and Family Fun Fest and Do Fashion ensures that there's a little something for everyone at Do Division Street Fest.

• 5. Windy City Hot Dog Fest

  (Portage Park, May 29-31) Decide once and for all—does ketchup belong on a hot dog? Join the debate at Chicago’s beloved Windy City Hot Dog Fest, happening Friday through Sunday, May 29-31, in the lively Portage Park neighborhood. Some of Chicagoland’s most iconic hot dog stands will compete head-to-head for the title of Best Frankfurter, and the best part—you get to be the judge!

• 6. Lincoln Park Greek Fest

  (Lincoln Park, Jun 5-7, 2026) St. George Greek Orthodox Church in the Lincoln Park area of Chicago’s north side and was established in 1923 by Greek immigrants. St. George remains an important center for worship and fellowship for its parishioners and friends from throughout the Chicagoland area.

• 7. Grant Park Music Festival

  (Grant Park, Jun 10 - Aug 15, 2026) A local staple for more than 90 years, the Grant Park Music Festival features an extraordinary line-up of classical music in the heart of downtown Chicago all summer long. This long-running concert series is the nation’s only free, summer-long outdoor festival dedicated to classical music

• 8. Puerto Rican Fest

  (Humboldt Park, Jun 11-14, 2026) The Humboldt Park neighborhood has the largest Puerto Rican population in the city and the center of Puerto Rican culture throughout the Midwest. Making this the perfect destination to celebrate Puerto Rican Day in Chicago.

• 9. Midsommarfest

  (Andersonville, Jun 12-14, 2026) Residents and visitors alike eagerly anticipate the arrival of Andersonville Midsommarfest, an annual celebration which transforms Clark Street into a haven of music, dance, and community spirit. Inspired by the Swedish Midsommar tradition, the festival takes place the second weekend in June, ushering in the summer season with a diverse array of festivities.

• 10. Logan Square Arts Fest

  (Logan Square, Jun 26-28, 2026) Each year, the festival highlights a variety of artists, neighborhood restaurants, and locally crafted beer and cocktails. In collaboration with neighborhood art organizations, the festival showcases visual art throughout the grounds, while local music venues provide a diverse lineup of performances that capture the essence of our community.

• 11. Rib Fest Chicago

  (Northcenter, Jun 5-7, 2026) One of Chicago’s most iconic summer festivals is back and bigger than ever! Whether you’re a BBQ connoisseur, a music lover, or just looking for an amazing weekend in Chicago, Ribfest Chicago is the place to be!

• 12. Square Roots Fest

  (Lincoln Square, Jul 10-12) Square Roots brings together the best of Lincoln Square, Chicago, and beyond, with a great lineup of live music, family fun, local restaurants and vendors, local craft beer, cocktails and much more!

• 13. Roscoe Village Burger Fest

  (Roscoe Village, Jul 17-19, 2026) This beloved Windy City tradition brings together Chicago’s top eateries, each serving up their juiciest, most creative takes on the classic burger.

• 14. Fiesta Del Sol

  (Pilsen, Jul 23–26, 2026) Free 4-day Latino festival in Chicago's Pilsen neighborhood (Cermak Rd between Ashland and Morgan), typically held in late July or early August

• 15. Chinatown Summer Fair

  (Chinatown, Jul 25-26, 2026) Highlights include the Dragon & Lion Dance Procession, artisans, plenty of great cuisine, activities for families and children, and more.

• 16. Wicker Park Fest

  (Wicker Park, Jul 24-26, 2026) Wicker Park Fest celebrates the eclectic neighborhood’s lively musical heritage, unique businesses and top-notch restaurants.

• 17. Chicago Italian Beef Fest

  (Jefferson Park, Jul 31 - Aug 2, 2026) Back in the early 1900s, Italian immigrants brought their culinary traditions to Chicago—and from their kitchens came a masterpiece now beloved across the city: the Italian Beef Sandwich. Whether you prefer it dipped, dry, or loaded with hot and sweet peppers, it all starts with tender, slow-cooked beef piled high on fresh bread.

• 18. Market Days

  (Boystown, Aug 7-9, 2026) Northalsted Market Days® is an annual street festival celebrating community in Chicago’s landmark Northalsted/Lakeview neighborhood.

• 19. Lakeview Taco Fest

  (Southport Corridor, Aug 21–23, 2026) Prepare your taste buds for a three-day fiesta that pays tribute to everyone’s favorite tortilla-wrapped delight. Whether you’re a fan of traditional fillings like chicken, steak, chorizo, and beef or crave innovative creations, this festival has it all! Over 10 of Chicago’s finest eateries will compete to craft the city’s most mouthwatering tacos.

• 20. Taste of Greektown

  (West Loop, Aug 28-30, 2026) Renowned as the heart of the city’s Greek restaurant scene, this iconic stretch of Halsted has been delighting locals and visitors with authentic flavors and lively traditions for decades.

• 21. Taste of Polonia Festival

  (Jefferson Park, Sep 4-7, 2026) Labor Day festival spanning 3 city blocks and featuring Polish food, cultural events, and music on multiple stages.

• 22. Chicago German-American Oktoberfest

  (Lincoln Square, Sep 11-13, 2026) Celebrate the arrival of fall in Lincoln Square at the Chicago German-American Oktoberfest, which sets up two gigantic tents in the neighborhood to serve liters of beer, stacks of pretzels and more German delicacies. The weekend also features a parade up Lincoln Avenue, live performances from four German bands and carnival games for the kids.

• 23. Retro on Roscoe

  (Roscoe Village, Sep 18-20, 2026) Stroll down Roscoe Street and soak in the nostalgic vibes, from decades-spanning hits on multiple stages to rows of rare and restored classic cars gleaming in the sun. Indulge in delicious eats from top local vendors, sip on craft beer, and let the kids enjoy the family-friendly games and activities in the dedicated children’s area.

• 24. World Dumpling Fest

  (Lincoln Park, Sep 19-20, 2026) World Dumpling Fest celebrates diverse cultures throughout Chicago and the world with music, dance, and of course, dumplings! The Chicago Cultural Alliance is excited to host their sixth annual World Dumpling Fest in it’s new Lincoln Park home.

• 25. Oktoberfest Chicago

  (Lincoln/Southport/Wellington, Sep 25-27, 2026) Expect a weekend packed with German food, craft beer from local and international breweries, and nonstop entertainment—including stein-holding contests, polka dancing, and an epic Sunday “Kinderfest” for the little ones. Whether you’re a beer aficionado, a pretzel enthusiast, or just here for the vibes, St. Alphonsus Oktoberfest is the place to be.

• 26. Jazz Fest

  (Hyde Park, Sept 26–27, 2026) For one unforgettable weekend, Hyde Park Jazz Festival transforms Chicago’s South Side into a jazz lover’s paradise!

• 27. Apple Fest

  (Lincoln Square, Oct 2-4, 2026) Apple Fest is a long standing tradition in Lincoln Square, bringing community together to celebrate the beginning of autumn.