It’s Fairs and Festival season and although many of our local favorites have had to cancel again this year, many others are moving forward following the CDC guidelines to ensure a safe and fun time for all. Please check with organizer before you go as circumstances may have changed since time of print.



  • Skokie Festival of Cultures – Multi mini events in May.  Cultural booths, folk music, dance, arts and crafts. Check back for locations in Skokie.
  • Wine on the Fox – 5/1 & 2. Entertainment, food and premier wine tasting. Hudson Crossing Park, Oswego.
  • Lilac Time Fair – 5/1 – 16. Art and craft vendors, food, entertainment and free Kids Zone. Downtown Lombard.
  • Food Truck Festival – 5/7. 5 to 10PM. 20 local and regional food trucks, art and live music. Benton St., Aurora.
  • Chocolate Festival – 5/14-16. Chocolate vendors, live music, children’s activities and roaming performers. Downtown Long Grove.

Kites in Flight – May 23. Chicago Kite will fill the skies above Heritage Harbor with colorful, awe inspiring kites of all sizes and designs. Watch the graceful beauty of the kites and wander through the craft and food vendors. Ottawa, IL 815-434-2737.

  • Belmont-Sheffield Music Fest – 5/29-30. Local tribute bands, family entertainment, arts and crafts vendors. Sheffield Ave., Chicago.


  • Taste of Wheaton – 6/3-6. Carnival, arts and crafts, and entertainment. Downtown Wheaton.
  • Lincoln Park Wine Fest – 6/4-6. More than 80 varietals, food/wine pairings, artists and dancing. Jonquil Park, Chicago.

Ottawa Uncorked – June 5-6. Enjoy wine from nearly 20 Illinois wineries! Sample and purchase wines made right here in Illinois, many of which are the product of Illinois-grown grapes. Fabulous food, amazing live music, outdoor arts and crafts market and much more! Downtown Ottawa. 815-434-2737.

  • Hinsdale Fine Arts Festival – 6/5-6. Show hosts 130 juried artists, food and kids’ activities. Downtown Hinsdale.
  • Old Canal Days – 6/10-13. Arts and crafts, carnival, entertainment, food, beer and wine tent. Downtown Lockport.
  • Ottawa 2 Rivers Wine Fest – 6/11-13. Local wine, fresh lobster, live jazz and outdoor market. Downtown Ottawa.
  • Old Town Art Fair – 6/12-13. Artists, urban garden walk, music and kids’ activities. Old Town Triangle Historic District, Chicago.
  • Wells Street Art Festival – 6/12-13.  Six-block art fair with music and kids’ play area. Old Town, Chicago.
  • Riverside Arts Weekend – 6/12-13. Juried artists, fashion show, live entertainment, kids’ activities. Guthrie Park, Riverside.
  • Blues on the Fox – 6/18-19. Popular blues artists perform at this annual event. Children welcome with parents. RiverEdge Park, Aurora.
  • Chicago Pride Fest – 6/19 – 20. Legendary two-day street festival all about LGBTQ+ life, culture and community. Chicago.
  • Wauconda Fest – 6/24-27. Carnival rides, wine tasting, car show and more. Main St., Wauconda.
  • Swedish Days Festival – 6/24-27. Entertainment, carnival rides, kids’ activities and parade. Geneva.
  • Homer Community Festival – 6/24-27. Carnival, live music, parade and fireworks. Heritage Park, Homer Glen.
  • Strawberry Fest – 6/25-27. Unique, strawberry-centric food, pie eating contents, carnival rides and entertainment. Downtown Long Grove.
  • Festival of the Arts – 6/26 – 27. Hundred juried artists from around the world in a variety of mediums. Highland Park.
  • Pride in the Park – 6/26-27. National and local music acts celebrating the LGBT community. Grant Park, Chicago.

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