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* Recommended
* Wine Enthusiast’s Toast of the Town Chicago, May 1
The Field Museum, 1400 S Lake Shore Dr. VIP tasting 6–7:30pm; Grand Tasting 7:30– 10:30pm; $95, VIP $185.
The wine connoisseur’s bible, Wine Enthusiast, has corralled some of the world’s best vineyards into the Field Museum. Pleasure your palate with tastings from 500 wines and spirits, and 30 top restaurants.
FREE Looptopia, May 2–3
Chicago River to Congress Pkwy and Clark St to Columbus Dr. Fri 5pm–Sat 7am.
While this follow-up to last year’s 24-hour party is only 14 hours, it will still rock every corner of the Loop with an all-night celebration of Chicago’s arts, culture and architecture.
FREE Seeds of Change Music Festival, May 3
Berry United Methodist Church, 4754 N Leavitt St at Lawrence Ave. 10am–4pm.
Seeds of Change, the organic marketplace, presents performances by puppet- and jug-toting bands, which run concurrently with the usual array of Toys of summer and sustainable vendors.
Lakeview Mayfest, May 16–18
3100 N Ashland Ave at Barry St. Fri 5–10pm, Sat, Sun noon–10pm; $5.
One of the first fests of the season gets you in the summer spirit. Pooches are invited on Sunday for the Chicago Pet Expo & Dog Show and pet parade.
* ZAP’s Zinfandel Grand Tasting, May 20
Mid-America Club, 200 E Randolph Dr between Columbus Dr and Stetson Ave, 80th floor. 6:30–8:30pm, $45.
* International Mr. Leather Weekend, May 22–26
Hyatt Regency, 151 E Wacker Dr between Michigan and Stetson Aves. Thu 8–11pm; Fri noon–7pm; Sat 11am–11pm; Sun 11am–9pm; Monday 11am–4pm; $165, premium advance tickets $190.
* Summer Camp Music Festival, May 22–25
Three Sisters Park, 17189 N Rt 29, Chillicothe.
About 140 miles southwest of Chicago, this huge, camping-friendly music fest features the Flaming Lips, the Roots, Girl Talk, Umphrey’s McGee and others.
* Chicago Gaelic Park Irish Fest, May 23–26
Gaelic Park, 6119 W 147th St, Oak Forest. Fri 3–11pm; Sat, Sun noon–11pm; Mon noon–8pm; $12–15, kids 11 and under free.
Irish music, theater happenings, carnival rides, bagpipers and ceili dancing make a good Celtic throwdown.
* Randolph Street Market Festival, May 24–Oct 26
Randolph St between Ada St and Ogden Ave. Saturdays 10am–5pm, Sundays 9am–4pm; $10, kids under 12 free.
The Chicago Antique Market returns this year with a new name and look. A few contemporary booths—selling global goods and vinyl—join more than 200 antique and vintage dealers on the last Sunday of each month through October.
Fiesta de Mayo, May 26
Plaza Garibaldi, 2600 S California Ave. Noon–8pm, $15–30.
FREE Chicago Turkish Festival, May 28–31
Daley Plaza, Washington and Dearborn Sts. 10am–6pm.
The city of Chicago and the Turkish-American community team up to present this festival of Turkish delights: paper-marbling, carpet and kilim demos; classical and modern Turkish music and dancing; and vendor booths. At lunchtime, feast like a sultan on baklava, Turkish coffee and other traditional favorites.
FREE Lincoln Square Mayfest, May 29–Jun 1
Lincoln and Leland Aves. Thu 5–9:30pm; Fri 5–11pm; Sat noon–11pm; Sun noon–10pm.
Good food, dancing and traditional keg tapping ensure a good time at this German fete.
* FREE Chicago Gospel Music Festival, May 30–Jun 1
Millennium Park, Michigan Ave between Monroe and Randolph Sts. Fri 4–9:30pm; Sat, Sun 11am–9:30pm.
Gospel-music performers and their fans take over Millennium Park for the 24th annual Chicago Gospel Music Festival. Percy Bady, from BET’s Sunday’s Best, will present “Gospel’s Next Showcase,” and award-winning roof-raisers the Clark Sisters, Lady Tramaine Hawkins and the Rance Allen Group perform.
Chi-Town Sta-bil Kruze, May 31
Soldier Field South Parking Lot, 18th St at Lake Shore Dr. 8am–3pm. Cruise 8–10am, car show 10am–3pm; car registration $20, viewers free.
Belmont-Sheffield Music Fest, May 31–Jun 1
Sheffield Ave between Belmont Ave and School St. Sat noon–10pm; Sun noon–9pm; $5.
The Why Store and Nine Days headline this North Side street fest.
FREE Do Division Street Fest and Sidewalk Sale, May 31–Jun 1
Along Division St, between Damen Ave and Leavitt St. Noon–10pm.
This weekend, the West Side hipster enclave boasts boutique discounts, a stage of bands curated by the Empty Bottle, and an ever-flowing supply of Pabst.