From Jennifer Roche,
Your Guide to Chicago.
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Festival season springs this month. Beginning with Looptopia and ending with Gospel Fest, May in Chicago never lets up. Here are our top picks for the month. Enjoy.

• Wine Enthusiast's Toast of the Town Tasting - Thursday, May 1
  Wine tasting and restaurant extravaganza at the Field Museum.

• Looptopia - Friday, May 2 to Saturday, May 3
  From dusk to dawn, the nation's first all night festival promises to percolate through the Loop for the second year of this incredibly vibrant event. 300 artists. 100 venues.

• Cinco de Mayo Festival and Parade - Friday, May 2 to Sunday, May 4
  More than 200,000 people attend this family-oriented celebration every year in Douglas Park (1401 S. Sacramento). The parade runs on May 4 beginning at noon on Cermak and Damen and heading west to Marshall Blvd.[/link]

• Poland in the Park - Sunday, May 3
  A celebration of Polish culture beginning with a parade at 11:30am followed by a fest in Millennium Park beginning at 2pm. Will include music, food, and entertainment.

• Out at Chicago History Museum - Thursday, May 8
  "Screaming Queens and Lavender Panthers: A History of Transgender Activism" lecture and reception. Starts at 5:30 pm.

• 16th Annual Chicago River Day - Saturday, May 10
  Join with thousands of other volunteers in the morning to help clean the Chicago River, then join them for a mega-BBQ at River Park (5100 N. Francisco) in the afternoon.

• Mother's Day - Sunday, May 11
  Love your mama, even if she's done you wronga. Find Chicago events and gift ideas to celebrate mom.

• Green City Market Opens - Wednesday, May 14
  The city's premiere farmers market opens just in time to rescue us from a dismal winter and hydroponic tomatoes. In fact, the farmers markets begin to open up all over the city this month and next. Find one near you with the guides below.
  • Downtown Chicago Farmers Markets
    
  • Chicago Neighborhood and Community Farmers Markets

• Chicago Places and Spaces Festival - Saturday, May 17 and Sunday, May 18
  Another name for this might be "Urbanist Fest." Come tour the city's architectural gems and neighborhood wonders through this celebration of our urban landscape.

• Chicago Green Festival - Saturday, May 17 and Sunday, May 18
  Tap into the city's green vibe and re-commit to a sustainable lifestyle at this Navy Pier event. Yoga. Organic Beer. Speakers. Eco-friendly products.

• 10th Annual Asian American Festival - Monday, May 19 to Friday, May 23
  Performances, lunch, street market and more every day in Daley Plaza from 9am to 5pm. Sponsored by the Korean American Association of Chicago.

• Chicago Antique Market Opens - Saturday, May 24 and Sunday, May 25
  The city's European style antique market kicks off its summer season.

• Bike the Drive - Sunday, May 25
  Lake Shore Drive is one of the loveliest drives in the world - why not bike it in this car-free, friendly event?

• Mayfest - Thursday, May 29 to Sunday, June 1
  Lincoln Square's summer celebration with a German flair.

• 24th Annual Gospel Music Festival - Friday, May 30 to Sunday, June 1
  It's all about praise, glory, and great voices. It's also proof that summer is here with the first Grant Park/Millennium Park festival of the season. More reason for praise, no?