Discover a calendar of Chicago area festivals and street fairs for May and June. Find details on each one including what to expect when you attend. These festivals are the best way to celebrate the season.



  • Wine on the Fox Fest – 5/7-8. Entertainment, food and premier wine tasting. Hudson Crossing Park, Oswego.
  • Aurora Greek Fest – 5/13-15. Greek food and culture celebration. St. Athanosios Greek Orthodox Church.
  • Tulip Time Festival – 5/7-15. Hundreds of tulips, entertainment, events and activities. Holland, MI
  • Chicago Critics Film Festival – 5/13-19. Acclaimed films plus appearances by directors and stars. Music Box Theatre, Chicago.
  • Blooming Fest – View plants, artwork, live music and family activities in West Chicago 9AM-3PM.
  • Chocolate Festival – 5/20-22. Chocolate vendors, live music, children’s activities and roaming performers. Downtown Long Grove.
  • What’s Blooming on Harrison – 5/21. Art fair, children’s carnival, music, food, beer garden and more. Oak Park.
  • Skokie Festival of Cultures – 5/21-22.  Cultural booths, folk music, dance, arts and crafts. Oakton Park, Skokie.
  • Northbrook Art in the Park – 5/21-22. 85 artists in many mediums, music, food, youth art activities. Northbrook.
  • Renegade Craft Spring Fair – 5/21-22. Andersonville. Details TBD.
  • Geek Fest – 5/21. Arcade Units, bouncy castle, obstacle course, vendors, board games. 1-4PM. Carol Stream.
  • Red, White and BBQ Festival – 5/27-29. Carnival rides, attractions and games. Westmont.
  • DuPage Community Arts Festival – Musicians and artists gather at the DuPage County Fairgrounds. 10AM-11PM
  • Belmont-Sheffield Music Fest – 5/28-29. Local tribute bands, family entertainment, arts and crafts vendors. Sheffield Ave., Chicago.
  • Prairie Arts Festival – 5/25-26. Fine art show, entertainment and kids’ activities. Robert O. Atcher Municipal Center, Schaumburg.
  • Taste of Mexico – 5/31-6/2. Authentic cuisine, music, carnival rides, arts and crafts. Little Village, Chicago.


  • 57th Street Art Fair – 6/1-2. 57th Street, Hyde Park.
  • Cream of Wheaton Festival – 6/2-5. Arts and crafts fair, carnival, Cosley Zoo and food vendors. Wheaton.
  • Rose Festival – 6/2-5. Rose parade, rides, concessions, and games. Roselle.
  • La Grange Carnival – 6/3-5. Rides, ferris wheel, games, concessions.
  • Maifest – 6/2-5. German celebration of food, music and maypole dance. Lincoln Square, Chicago.
  • Ottawa 2 Rivers Wine Festival – 6/3-5. Tasting from local wineries and artisan market.
  • Lincoln Park Wine Fest – 6/3-5. More than 80 varietals, food/wine pairings, artists and dancing. Jonquil Park, Chicago.
  • Rosemont Uncorked Wine Festival – 6/4-5. 18 wineries, live music and more.
  • Dragon Boat Festival – Dragon boat races, music, food, drinks and more. Blue Island.
  • Chicago Gospel Music Festival – 6/4. Jay Pritzker Pavillion, Millennium Park.
  • Cavalcade of Planes – 6/4-5. Warbirds on display and flying, food vendors, airplane and helicopter rides. Bolingbrook.
  • Ottawa Uncorked – 6/5-6 20 Illinois wineries, food, live music, outdoor arts and crafts market, more. Ottawa

Strawberry Jazz Festival | June 5 – 11AM-4PM.  Art, Handmade Crafts, Live Entertainment, Food Trucks, Kid Zone. Free Admission. Free Parking. Northfield Square Mall, Route 50 @ I-57 (Exit 315). Bradley, Illinois.

  • Hinsdale Fine Arts Festival – 6/4-5. 130 juried artists, food and kids’ activities. Downtown Hinsdale.
  • New Orleans North – New Orleans comes to downtown Joliet, music, local artists, food and performers. Joliet.
  • Franklin Park Fest – 6/9-6/12. Daily carnival, live music, food vendors and more. Franklin Park.
  • Old Canal Days – 6/9-12. Arts, crafts, carnival, entertainment, food, beer and wine tent. Downtown Lockport.
  • Mundelein Craft Beer Festival – 6/11. Save The Date. Mundelein.
  • Global Arts Festival – 6/11-12. Multicultural music, art, crafts, dance and kids’ activities. Jim Jenson Pavillion, Bartlett.
  • Family Pride Festival – 6/11. Pet parade, kids show, drag shoe, food trucks and artisan booths. Washington Park. Ottawa.
  • Old Town Art Fair – 6/11-12. Artists, urban garden walk, music and kids’ activities. Old Town Triangle Historic District, Chicago.
  • Wells Street Art Festival – 6/11-12.  Six-block art fair with music and kids’ play area. Old Town, Chicago.
  • Riverside Arts Weekend – 6/11-12. Juried artists, fashion show, live entertainment, kids’ activities. Guthrie Park, Riverside.
  • Aurora Pride Festival and Parade – 6/12. Updates coming soon. Aurora.
  • Taco & Tequila Fest – 6/15. Tacos, tequila-infused cocktails and dancing. Ages 21+. Lincoln Park, Chicago.
  • Woodridge Jubilee – 6/15-6/18. Carnival rides for all ages, food, entertainment, bingo. Woodridge.

PrairieFest | June 16 – 19 – Children’s activities, concerts, carnival rides, pony rides, business expo, and food vendors. Free admission and parking. As seen on Food Network. Oswego.

  • Libertyville Days Festival – 6/16-19. Carnival rides, arts, crafts, music and parade. Downtown Libertyville.
  • Scottish Festival and Highland Games – 6/17-18. Traditional Scottish games, exhibits, music and food. Hamilton Lakes, Itasca.
  • Minooka Summerfest – 6/17-18. Save the Date, details coming soon. Minooka.
  • 33rd Annual Ribfest – 6/17-6/20.  Award-winning ribs, family fun area, entertainment and more. Wheaton.
  • Taste of Des Plaines – 6/17-18. Local food vendors, entertainment, games, beer and wine area. Des Plaines.
  • Grayslake Arts Festival and Wine Tasting – 6/18. Whitney Street, Municipal Parking Lot. Grayslake.
  • Solstice Hop & Vine Fest – 6/18. Entertainment, food, wine and beer. Ages 21+. Meineke Park, Schaumburg.
  • Folk Fest – 6/18. Music, games, food vendors. Cantigny. Wheaton.
  • Winnetka Music Festival – 6/18. Live music, food trucks, beer and wine. Winnetka.
  • Chicago Pride Fest – 6/18–19. Legendary two-day street festival all about LGBTQ+ life, culture and community. Chicago.
  • Homewood-Flossmoor Juneteenth Festival – 6/19. Community choir, music, vendors and parade. Flossmoor.
  • Craft Beer & Wine Festival – 6/20. Live music, food and more than 60 beers and wines. Ages 21+. Heritage Park, Wheeling.
  • Swedish Days Festival – 6/22-26. Entertainment, carnival rides, kids’ activities and parade. Geneva.
  • Homer Fest – 6/23-6/26. Food vendors, live music, parade and more. Homer Glen. Facebook/homercommunityfest

Rotary GroveFest – June 23 – 26 – Live Music • Unlimited Rides • Food/Biz Expo. Huge Beer Garden/Entertainment Area. Downtown Downers Grove.

  • Wauconda Fest – 6/23-26. Carnival rides, wine tasting, car show and more. Main St., Wauconda.
  • Homer Community Festival – 6/23-26. Carnival, live music, parade and fireworks. Heritage Park, Homer Glen.
  • Strawberry Fest – 6/24-26. Unique, strawberry-centric food, pie eating contents, carnival rides and entertainment. Downtown Long Grove.
  • Taste of Joliet – 6/24-26. Food vendors, carnival rides, kids’ zone and headline entertainment. Joliet Memorial Stadium.
  • Pride in the Park – 6/25-26. National and local music acts celebrating the LGBT community. Grant Park, Chicago.

Arlington Heights Frontier Days Festival – June 30 – July 4. FREE ADMISSION, FREE Music Entertainment, Carnival Rides, 4th of July Parade, Food, Beer, Wine, Bingo, Family Activities, Pony Rides, 3v3 Soccer, Stampede Run 5K/10K, & more! Recreation Park, Arlington Heights.

  • The Dole’s Lakeside Festival – 6/30-7/3. Live music, food, carnival rides, games, kids’ activities. Dole Mansion.
  • Palatine Hometown Fest – 6/30-7/4. Live bands, food vendors, carnival, craft fair. Palatine.


DuPage County Fair | July 29 – 31. Come One, Come All – Neighbors, Friends, and Family. Live music, carnival, food, petting zoo, rodeo, livestock show and contests.

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