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* Wine Enthusiast’s Toast of the Town Chicago, Apr 30 The Field Museum, 1400 S Lake Shore Dr (wineenthusiast.com/toast). VIP tasting 6–7pm, Grand Tasting 7– 10pm; $95, VIP $175. 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 Mayor Daley’s Kids & Kites Festival, May 2 Montrose Harbor, Montrose Ave and Lake Shore Dr (chicagokidsandkites.us). 10am–4pm. Kids catching wind of this daylong kite celebration—replete with kite flying, decorating, storytelling and crafts—are guaranteed to get extra high at the new “big kite candy drop” where sweet treats appear to fall from the sky.
Lakeview Mayfest, May 15–17 Ashland Ave at Barry St (starevents.com/mayfest). Fri 5–10pm; Sat, Sun 10am–10pm; $5. If you’ve been told that you resemble your pooch, don’t be offended. Instead, sign up for the Pet Parade’s “Owner Look-A-Like” competition, the highlight of this North Side neighborhood fest.
* International Mr. Leather Weekend, May 21–25 Chicago Hilton, International Ballroom, 720 S Michigan Ave (imrl.com). Thu 8–11pm; Fri noon–7pm; Sat 11am–11pm; Sun 11am–9pm; Mon 11am–4pm; $165, premium advance tickets $190. These macho, macho men strut their stuff for a 31st season. The four-day affair includes the leather competition, parties, exhibits and the popular market where shoppers can choose from cowhide belts, hats, vests or whips; we don’t judge.
Chicago Gaelic Park Irish Fest, May 22–25 Gaelic Park, 6119 W 147th St, Oak Forest (chicagogaelicpark.org). Fri 3–11pm; Sat, Sun noon–11pm; Mon noon–8pm; $15, kids 12 and under $12, kids 2 and under free. The Celtic throwdown is a mix of bagpipers, Irish step-dancers and musical acts including Beatles look-alikes American English. The fest attempts to get your whole family in on the fun with the “red-hair and freckled-face” contest, Gaelic football, hurling and more.
* Decibelle Music and Culture Festival, May 22, Jun 4–6, Sept 24–26 Several venues including Empty Bottle, 1035 N Western Ave (decibelle.org). Times vary. $20–$25. Formerly known as Estrojam, this multi-part feminist festival brings in bad-ass girl acts like Peaches, Ssion and Ongina from RuPaul’s Drag Race.
Summer Camp Music Festival, May 22–24 Three Sisters Park, 17189 N Rt 29, Chillicothe (summercampfestival.com/2009). $140 three-day pass. About 140 miles southwest of Chicago, this huge, camping-friendly music fest features Willie Nelson, Umphrey’s McGee, Method Man and Redman and others.
* Randolph Street Market Festival, May 23–Sept 27 Randolph St between Ada St and Ogden Ave (chicagoantiquemarket.com). Saturdays 10am–5pm, Sundays 10am–4pm; $10, kids under 12 free, season pass $75. The ultimate urban market is back with more than 150 vendors. Come swap and shop at the three new mini-marts: the Vinyl Swap Meet, the Fancy Food Market and the Global Goods Bazaar. The market runs the last weekend of each month, May–Sept.
FREE Chicago Turkish Festival, May 27–30 Daley Plaza, Washington and Dearborn Sts (chicagoturkishfestival.org). 10am–6pm. Scrap your bag lunches and head to this celebration for Turkish delights, such as baklava, mado (Turkish ice cream) and other goodies. Enjoy Sufi dances, traditional music, a fashion show, art and more.
FREE Lincoln Square Mayfest, May 28–31 Lincoln and Leland Aves (lincolnsquare.org). Thu 5–9pm; Fri 5–11pm; Sat noon–1pm; Sun noon–10pm. Good food, dancing and traditional keg tapping ensure a good time at this German fete.
Belmont-Sheffield Music Fest, May 30, 31 Sheffield Ave between Belmont Ave and School St (chicagoevents.com). Sat noon–10pm; Sun noon–9pm; $5. Mix and mingle with other North Siders.
Do Division Street Fest and Sidewalk Sale, May 30, 31 Along Division St between Ashland Ave and Leavitt St (do-divisionstreetfest.com). Noon–10pm, $5. Sift through racks of discounted übertrendy clothing while sipping cold beer from local bars and listening to deejayed tracks.
The best spots at Chicago’s summer fests | Index fun | How to dress for this summer’s festivals | Chicago’s summer ethnic festivals | Cheap drinks at Chicago’s summer festivals | Festival treats cost plenty of cash, calories | Cheap summer thrills | What and where to buy at this summer’s festivals | Volunteering at music fests can get you in free | Money-saving tips!