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- May 3: Plant Sale Fundraiser
- May 8: 2008 Wicker Park Fest Applications
- May 11: Celebrate Mothers Day in Samba Style
- May 15: "Toast to Spring" Member Networking Event
- May 16: Colori Chicago Event
- May 17: Milwaukee Ave Landmark District-Immigrants Path to Prosperity
- May 18: WP Landmark District- Neighborhood that Changes but Stays the Same
- May 19: Shape Up For Summer Sale
- May 31: Annual Spring Wicker Park Antique & Junque Sale
- May 31: Do Division Street Fest & Sidewalk Sale 2008