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Summer Guide: Fairs & Festivals 

Street fairs, art fairs, neighborhood fests, and much more

Taste of Chicago

Taste of Chicago

Weekends (and some weekdays) throughout the summer feature a plethora of street fairs, festivals, and other community events. Admission fees listed for most neighborhood festivals are suggested donations for charity or community projects. —Sam Worley

May

Chicago Gaelic Park Irish Fest An exhibit from the Irish Music Archives, Connemara ponies, exhibition Gaelic football and hurling matches, carnival rides, live music, and more.  5/28-5/31, Fri 3-11 PM, Sat-Sun noon-11 PM, Mon noon-8 PM, Chicago Gaelic Park, 6119 W. 147th, Oak Forest, 708-687-9323, chicagogaelicpark.org, $15, $12 for seniors and kids 4-12, free for kids under 4.

International Mr. Leather This huge annual event for leatherfolk and sundry fetishists features contests, party upon party, and the crowning of International Mr. Leather 2010.  5/28-5/31, Fri 11 AM-2 AM, Sat 11 AM-2 AM, Sun 11 AM-4 AM, Mon 4 PM-4 AM, Hyatt Regency, 151 E. Wacker, 312-565-1234, imrl.com, $165-$195 weekend passes; prices for individual events vary.

Belmont-Sheffield Music Festival Trippin Billies and Wedding Banned headline.  5/29-5/30, Sat noon-10 PM, Sun noon-9 PM, Sheffield between Belmont and School, $5.

Randolph Street Market Festival The biggest attractions here are the Chicago Antique Market, with 150 vendors selling furnishings, housewares, clothing, jewelry, and more, and the Indie Designer Market, where you can buy directly from the designers and artists. Smaller markets include a vinyl swap meet, a "Fancy Food Market" promising truffles and rare olive oils and spices, a bazaar for artisans from Chicago's ethnic communities, and the "Do-It-Yourself Estate Sale." On Sun 5/30 admission is free for participants in Bike the Drive.  5/29-5/30, 6/19-6/20, 7/24-7/25, 8/28-8/29, 9/25-9/26, Sat 10 AM-5 PM, Sun 10 AM-4 PM, Plumbers Hall, 1340 W. Washington, 312-421-1010, randolphstreetmarket.com, $10, $8 advance, $5 students.

June

Mayfest Chicago You'll find good old-fashioned gemütlichkeit and an actual maypole at this Lincoln Square festival.  6/3-6/6, Thu 5-9:30 PM, Fri 5-11 PM, Sat noon-11 PM, Sun noon-10 PM, 4700 N. Lincoln (at Leland), mayfestchicago.com

Beer Hoptacular Craft brewers talk up and sample out their wares in three sessions, each with food pairings provided by Whole Foods.  6/4-6/5, Fri 6:30-10:30 PM, Sat 1-5 PM and 6:30-10:30 PM, Aragon Ballroom, 1106 W. Lawrence, 773-561-9500 or 312-559-1212, beerhoptacular.com, $45.

Eastside Millennium Art Festival 150 artists on three blocks, with live music and food.  6/4-6/6, Fri 11 AM-5 PM, Sat-Sun 10 AM-5 PM, Lake and Michigan, amdurproductions.com/f-eastside-public.html

57th Street Art Fair The oldest juried art fair in Chicago includes an "art-buying boot camp" (a guided tour of the booths to show you what to look for). The fair is alcohol-free.  6/5-6/6, Sat 11 AM-6 PM, Sun 10 AM-5 PM, 57th and Kimbark, 773-493-3247, 57thstreetartfair.org

June Jam Family-friendly street fair with music, kid-oriented games and activities, and food.  6/5-6/6, Sat noon-10 PM, Sun noon-9 PM, 3500 N. Hoyne, starevents.com/festivals-events/june-jam/, $5.

Constructor Craft Fair "Bad-ass crafters unite under one roof to overthrow the western suburbs," promise the organizers of this festival. Crafts from more than 30 vendors, food, and free gift bags for the first 50 arrivals.  Sun 6/6, 10 AM-6 PM, Fitzgerald's, 6615 Roosevelt, Berwyn, 708-788-2118 or 866-468-3401, constructorcraftfair.com

Sketchbook Collaboraction's annual performing arts festival features short original works (seven minutes or less), plus live music and visual art.  6/10-6/27, Chopin Theatre, 1543 W. Division, collaboraction.typepad.com, $20-$35.

Taste of Bryn Mawr Food samples and sales on merchandise from participating Edgewater businesses.  Thu 6/10, 6-9 PM, starts at 1058 W. Bryn Mawr, 773-506-4016, edgewaterdev.org, $35, $25 in advance, $10 kids under 12.

Party at St. Mike's This annual event, timed to coincide with the Old Town Art Fair, features a beanbag tournament and live music, including headliners Better Than Ezra.  6/11-6/13, Fri 5-10 PM, Sat 3:30-10 PM, Sun 3-9 PM, Saint Michael's Church, 1633 N. Cleveland, 312-642-2498, st-mikes.org, $5 Fri and Sun, $10 Sat, $12 weekend pass.

Andersonville Midsommarfest Celebrating Andersonville's Swedish heritage with eats and entertainment.  6/12-6/13, 11 AM-10 PM, Clark between Foster and Catalpa, starevents.com/festivals-events/andersonville-midsommarfest, $5.

Chicago Botanic Garden Wine Festival More than 200 wines, along with cooking demos, food vendors, wine seminars, and live music.  6/12-6/13, noon-6 PM, Chicago Botanic Garden, 1000 Lake Cook, Glencoe, 847-382-1480, chicagobotanicgardenwinefestival.com, $35, $25 advance, $10 designated driver ticket.

Drinking & Writing Festival Sponsored by Drinking & Writing Brewery ("exploring the connection between creativity and alcohol since October 17, 2002"), the sixth iteration of this annual festival is dedicated to beloved Chicago journalist Mike Royko. Speakers include Northwestern prof Bill Savage, urban social scientist Denese Neu, Chicago Bar Project's Sean Parnell, and special guest David Royko.  Sat 6/12, noon-5 PM, Hopleaf, 5148 N. Clark, 773-334-9851, drinkingandwriting.com, $25, $20 in advance.

Humboldt Park Art Fair Put on by emerging artists for emerging artists, this year's fair features dozens of artists and musical acts.  Sat 6/12, noon-9 PM, Humboldt Park Boat House, 1301 N. Sacramento, 312-742-7549, graffitizone.org. F

Old Town Art Fair Juried show of more than 260 artists, plus live music and activities for kids.  6/12-6/13, 10 AM-6 PM, Lincoln and Wisconsin, 312-337-1938, oldtowntriangle.com, $7.

Wells Street Art Fair One of the city's bigger art fairs, with music from Trippin Billies and Rock Candy.  6/12-6/13, 10 AM-10 PM, Wells between North and Division, chicagoevents.com/event.cfm?eid=141, $7-$10.

Chi-Town Kruze More than 500 hot-rod owners show off their vehicles in a parade that begins and ends at Standard Bank Stadium, followed by a classic car show from 10 AM to noon. Benefits Ronald McDonald House Charities of Chicagoland and Northwest Indiana.  Sun 6/13, 8-10 AM, Standard Bank Stadium, 14011 Kenton, Crestwood, 708-489-2255, chitownkruze.com

Greater Chicago Jewish Festival Now in its 30th year, this festival includes a kosher food fair, an art fair, activities for kids, and musicians David Broza, the Guy Mendilow Band, and others.  Sun 6/13, 11 AM-6 PM, Cook County Forest Preserve, Oakton west of Lehigh, Morton Grove, 847-933-3000, jewishfestival.net, $5.

Fiestas Puertorriquenas For nearly a week, attendees celebrate Puerto Rican heritage with food, carnival rides, dance, and live music. The 44th annual Puerto Rican Day Parade is Sat 6/19 at noon, starting at Columbus and Balbo.  6/15-6/20, Tue-Fri 4-10:30 PM, Sat-Sun 1-10:30 PM, Humboldt Park, 1440 N. Sacramento, 773-292-1414, prparadechicago.org

Grant Park Music Festival Guest conductors and instrumentalists season the Grant Park Orchestra's renditions of everything from Vivaldi to Dvorak.  6/16-8/21, every Wed, Fri, and Sat (except 7/2 and 7/3) and a few other days, Jay Pritzker Pavilion Stage at Millennium Park, 201 E. Randolph, grantparkmusicfestival.com

Just for Laughs Five nights, 12 venues, and more than 100 comedians, including Ellen DeGeneres, Cedric the Entertainer's Urban Circus, Denis Leary, and Aziz Ansari. Venues include the Vic, the Park West, and the Chicago Theatre.  6/16-6/19, various times, justforlaughschicago.com, prices vary.

Bronzeville Cultural Festival Includes a book fair, film festival, and opening gala with live music and an awards ceremony.  6/17-6/18, Film Row Cinema, Columbia College, 1104 S. Wabash, eighth floor, 773-651-0700, bronzefest.com, $25 for opening gala/all other events are free. 

SummerDance Concerts in a variety of genres preceded by free dance lessons in the relevant style.  6/17-8/29, Thu-Sat 6-9:30 PM, Sun 4-7 PM, Spirit of Music Garden, Grant Park, 601 S. Michigan, 312-742-4007, chicagosummerdance.org

Festa!Pasta!Vino! Italian Street Festival Italian festival with live entertainment, food from local restaurants, and imported merchandise.  6/18-6/20, Fri 5-11 PM, Sat noon-11 PM, Sun noon-10 PM, Oakley and 24th, oshows.com, $3-$7.

Midsummer Festival Another Scandinavian solstice festival, with live music, arts and crafts, and activities for kids.  6/18-6/20, Fri 6-10 PM, Sat noon-10 PM, Sun noon-8 PM, Bryn Mawr between Lincoln and Western, chicagoevents.com/event.cfm?eid=203, $5.

Scottish Festival & Highland Games Celebration of Scottish culture including bagpipe music, Highland dancing, Scotch whisky tastings, rugby sevens, live music, and more.  6/18-6/19, Fri 4-10 PM, Sat 8 AM-9 PM, Oak Brook Polo Grounds, 700 Oak Brook, Oak Brook, 630-368-6428, chicago-scots.org, $9-$15, kids under 13 free, VIP pass $75, $70 advance.

Cantigny Art Festival Annual art fair with more than 150 vendors.  6/19-6/20, 10 AM-5 PM, Cantigny Park, 1S151 Winfield, Wheaton, 630-668-5161, cantigny.org

Custer's Last Stand Art festival with 30 food vendors, commercial stands from 150 local businesses, and live music.  6/19-6/20, 10 AM-9 PM, Chicago and Main, Evanston, 847-328-2204, custerfair.com

Latino Theatre Festival The Goodman presents the fifth biennial installment of this festival. Some events are free, including Insects, a show by Catalan street theater troupe Sarruga that "transforms Millennium Park's Chase Promenade into a fantasy world" replete with giant ants, spiders, and praying mantises (7/16-7/18).  6/19-7/25, various locations, 312-443-3800, goodmantheatre.org, prices vary.

Latin Street Salsa Congreso 2010 Formerly the Chicago Salsa Festival, this event includes five nights of dancing, performance, and workshops, as well as qualifying rounds for the World Salsa Championships. Locations include the Palmer House Hilton, Navy Pier, Excalibur Nightclub, and Grant Park.  6/23-6/27, Wed 6-9 PM, Thu 10 PM, Fri 7 PM-4 AM, Sat 7 PM-3 AM, Sun 1 PM-2 AM, 312-427-2572, latinstreetcongreso.com, $10-$25 per event.

Bloomington Gold Corvette Show National Corvette show, now in its 38th year.  6/24-6/27, 7 AM-5 PM, Pheasant Run Resort, 4051 E. Main, Saint Charles, 309-888-4477, bloomingtongold.com, $20, $15 advance, four-day pass $50, $40 advance.

Chicago Arabesque Food, handicrafts, music, and dance from across the Middle East.  6/24-6/26, Thu-Fri 10 AM-6 PM, Sat 11 AM-7 PM, Daley Plaza, 50 W. Washington, 312-744-3315, chicagoarabesque.com

Cans Music Fest Headliners this year are Coolio and Wang Chung.  6/25-6/26, 4 PM, Cans Bar and Canteen, 1640 N. Damen, 773-227-2277, cansbar.com/chicago, $5.

Chicago Pride Fest Arts and crafts, food, and live entertainment on two stages, including performances by Sixteen Candles and Wedding Banned.  6/25-6/27, Fri 3-10 PM, Sat 11 AM-10 PM, Halsted and Waveland, chicagopridecalendar.org, $7.

Long Grove Strawberry Festival Strawberries, chocolate-dipped strawberries, strawberry baked goods, and more.  Fri-Sun 6/25-6/27, Long Grove Historic Village, Old McHenry and Robert Parker Coffin, Long Grove, 847-634-0888, longgroveonline.com/strawberry.html, $2. 

Chicago Caribbean Jerkfest Celebration of pan-Caribbean culture with food, live music, and crafts, dedicated to raising awareness of HIV/AIDS in communities of color in the midwest and the Caribbean.  Sat 6/26, 11 AM-10 PM, Stateway Gardens, 3658 S. State, chitownjerkfest.com, $10, free for seniors and kids under 11.

Chicago Dyke March This more political, less commercial alternative to the pride parade left its longtime Andersonville home a few years ago, and now moves around the city every two years; this year it's in South Shore. A rally kicks off the event, and DJs and performances follow. The starting point is 7054 S. Jeffery, and the march moves north to end at Jackson Park (63rd and Hayes).  Sat 6/26, 2:30 PM, chicagodykemarch.wordpress.com

Chicago Summerfest Art show, family area, and live music.  6/26-6/27, Sat noon-10 PM, Sun noon-9 PM, Lincoln Park, Clark and Armitage, 773-665-4682, starevents.com/festivals-events/summerfest, $5.

Fountain Square Art Festival Juried fine arts fair with more than 200 artists.  6/26-6/27, 10 AM-6 PM, Sherman and Church, Evanston, chicagoevents.com/event.cfm?eid=123.

Tour de Fat A bike parade followed by a car funeral, rides on art bikes, and plenty of beer from New Belgium. One preselected person will renounce driving and trade his or her car for a new bike (to enter the contest, go to newbelgium.com/trade).  Sat 6/26, 9 AM-4 PM, Palmer Square, 3100 W. Palmer, 773-782-9471, newbelgium.com/tour-de-fat.

Pride Parade The 41st annual parade travels north on Halsted from Belmont to Broadway, south on Broadway, and east on Diversey to Cannon.  Sun 6/27, noon, chicagopridecalendar.org.

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