Whether you like your summer weekends loud with a side of light beer or a little more eclectic, the options for fairs and festivals that suit your mood are plentiful. Admission fees listed for most neiighborhood festivals are suggested donations for charity or community projects.
May
International Mr. Leather Chicago’s homegrown leather-man competition packs the weekend full with mixers, parties, and gear demos, concluding with the “Black and Blue Ball.” Mon 5/30 from 8 PM-4 AM at Excalibur Nightclub (632 N. Dearborn). 5/27-5/30: Fri noon-2 AM, Sat 11 AM-2 AM, Sun-Mon 11 AM-4 AM, Hyatt Regency, 151 E. Wacker, 800-545-6753, imrl.com, $165-$195 weekend passes; prices for individual events vary.
Belmont-Sheffield Music Festival Too White Crew and Wedding Banned headline. Sat 5/28, 12-10 PM, 3200 N. Sheffield, 773-584-6654, chicagoevents.com, $5
June
Mayfest Chicago You’ll find good old-fashioned gemtülichkeit and an actual maypole at this Lincoln Square festival. 6/2-6/5, Thu 5-9:30 PM, Fri 5-11 PM, Sat noon-11PM, Sun noon-10 PM, May Fest Chicago, 4700 N. Lincoln, mayfestchicago.com. 
Eastside Millennium Art Festival 150 artists on three blocks, with live music and food. 6/3-6/5, Fri noon-5 PM, Sat-Sun 10 AM-5 PM, 100 E. Lake, amdurproductions.com/f-eastside-artist.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 family-friendly and alcohol-free. 6/4-6/5, 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. 6/4-6/5, noon-10 PM, 3500 N. Hoyne, 773-665-4682, starevents.com/events/june-jam, $5.
SausageFest Chicago This Wrigleyville festival, formerly the Lake View Music Fest, will feature live music and arts and crafts besides the meat it is now named for. Smoking Pipes and Sixteen Candles headline. 6/4-6/5, noon-10 PM, 1000 W. Addison, 773-868-3010, chicagoevents.com, $5-$7.
Party at St. Mike’s This annual event, timed to coincide with the Old Town Art Fair, features a beanbag tournament and three days of live music, including headliners Maggie Speaks, Hairbanger’s Ball, and 7th Heaven. 6/10-6/12, 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, $20 weekend pass includes 3 beer tickets.
Andersonville Midsommarfest Commemorate Andersonville’s Swedish heritage with eats and entertainment. 6/11-6/12, 11 AM-10 PM, 5356 N. Clark, 773-665-4682, andersonville.org, $5.
Old Town Art Fair Juried show of more than 260 artists, plus live music and activities for kids. 6/11-6/12, 10 AM-6 PM, 312-337-1938, oldtowntriangle.com, $7, kids under 12 free.
Fiestas Puertorriquenas Celebrate Puerto Rican heritage with food, carnival rides, dance, and musical entertainment. The 44th annual Puerto Rican Day Parade is Sat 6/18 at noon, starting at Columbus and Balbo. 6/14-6/19, Tue-Fri 4-11 PM, Sat-Sun noon-11 PM, Humboldt Park, 1400 N. Humboldt, sponsorchicago.com/fiestas/index.html.
Just for Laughs Five nights, 12 venues, and dozens of comedians, including Seth Meyers, Louis C.K., Joel McHale, Demitri Martin, and Steve Martin and Martin Short in conversation. Venues include the Chicago Theatre, the Vic, and Park West. 6/14-6/18, various times, justforlaughschicago.com, prices vary.
Grant Park Music Festival Guest conductors and musicians season the Grant Park Orchestra’s versions of songs from Brahms to Broadway. 6/15-8/20, every Wed, Fri, and Sat (except 6/29) and a few other days, Pritzker Pavilion, Millennium Park, 201 E. Randolph, 312-742-1168, grantparkmusicfestival.com.
Festa Pasta Vino Italian festival with live entertainment, food from local restaurants, and imported merchandise. 6/17-6/19, Fri 5-11 PM, Sat noon-11 PM, Sun noon-10 PM, 2400 S. Oakley, 630-962-7000, oshows.com.
Custer’s Last Stand Art festival with 30 food vendors, commercial stands from 150 local businesses, live music, and an Eco-Village that features healthy cooking demos and eco-friendly vendors. 6/18-6/19, 10 AM-9 PM, Main & Chicago, Evanston, 847-328-2204, custerfair.com, $1.
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, 2600 W. Bryn Mawr, chicagoevents.com, $5.
6 Corners BBQ Fest This new Portage Park festival offers music, a market, and meat. 6/18-6/19, Sat noon-10 PM, Sun noon-8 PM, 4050 N. Milwaukee, 773-685-9300, sixcornerschicago.com, $5.
Make Music Chicago This festival, new to Chicago, fills Chicago’s public spaces with musicians of all kinds for a day, culminating in a concert at St. James Cathedral Commons, broadcast live on WFMT. Tue 6/21, 7 AM-9 PM, St. James Cathedral, 65 E. Huron, 773-850-0662, makemusicchicago.com.
Chicago Pride Fest Food and music on two stages, one dedicated to Chicago’s gay performers. 6/24-6/25, Fri 3-10 PM, Sat 11 AM-10 PM, 3712 N. Broadway, 773-868-3010, www.chicagoevents.com, $7-$10.
Taste of Chicago The venerable restaurant bonanza that clogs arteries and downtown streets. 6/24-7/3, Fri 6/24-Sat 7/2 11 AM-8:30 PM, Sun 7/3, 11 AM-6 PM, Grant Park, Columbus & Jackson, 312-744-3315, explorechicago.org.
Chicago Summerfest Art show, family area, and live music with headliners Hairbangers Ball and 16 Candles. 6/25-6/26, Sat 11 AM-10 PM, Sun noon-9 PM, Lincoln Park Cultural Center, 2045 N. Lincoln Park West, 312-742-7726, starevents.com/events/summerfest, $5.
Fountain Square Art Festival Juried fine arts fair with more than 200 artists, centered around a large sculpture garden. 6/25-6/26, 10 AM-6 PM, 1700 Sherman, Evanston, 773-868-3010, chicagoevents.com, $5.
Pride Parade 250 floats, decorated cars, bands, and more make up the Pride Parade, the massive party that moves through Boys Town every end of June. The parade starts at Halsted and Belmont, moves north and then turns back south on Broadway, and then turns east to Cannon on Diversey. Sun 6/26, noon, chicagopridecalendar.org.
July
Chicago Botanic Garden Art Festival 80 juried artists whose pieces incorporate plants line the garden’s esplanade for this new festival, with art demos, music, and activities for kids. 7/1-7/3, 10 AM-5 PM, Chicago Botanic Garden, 1000 Lake Cook, Glencoe, 847-926-4300, chicagobotanic.org.
SummerDance Concerts in a variety of genres preceded by free dance lessons in the relevant style. 7/7-9/18, Thu-Sat 6-9:30 PM, Sun 4-7 PM, Spirit of Music Garden, Grant Park, 601 S. Michigan, 312-742-4007, chicagosummerdance.org.
Eye on India This new festival will feature Indian dance, food, music, theater, film, and more at venues around Millennium Park. 7/8-7/17, Millennium Park, Michigan & Randolph, 773-327-3890, millenniumpark.org, prices vary.
North Michigan Avenue Art Fair In its 20th year, this juried River North fair boasts its inclusion in the Top 100 Art Festivals in the U.S., by Sunshine Artist magazine. 7/8-7/10, Fri-Sat 10 AM-6 PM, Sun 10 AM-5 PM, Pioneer Court, 401 N. Michigan, artfestival.com.
Chicago Folk & Roots Festival An eclectic lineup of musicians plays over the course of this two-day festival, presented by the Old Town School of Folk Music. 7/9-7/10, noon-9:30 PM, Welles Park, 2333 W. Sunnyside, 773-728-6000, chicagofolkandroots.org, $10, $5 seniors and kids.
Chicago Luxury Ice Cream Festival More than two dozen chefs, creameries, and pastry artists create unusual ice creams for sampling and compete against other chefs in the Great Chicago Brain Freeze. 7/9-7/10, Sat noon-5 PM and 6-9 PM, Sun noon-7 PM, Grand Piazza, 1431 W. Taylor, 312-226-5566, chicagoicecreamfestival.com, price TBA.
Gold Coast Art Fair 450 juried artists, food, and live music. 7/9-7/10, 9 AM-7 PM, Grant Park, Columbus & Jackson, 312-744-3315, amdurproductions.com.
Rock Around the Block Stretched over four Lakeview blocks—which center around the intersection of Belmont, Lincoln, and Ashland—this festival claims 40,000 Chicagoans will show up. 7/9-7/10, noon-10 PM, 3200 N. Lincoln, starevents.com/events/rock-around-the-block, $5.
Halsted Tastes Better All-you-can-eat chow from North Halsted neighborhood restaurants. There’s also live music and a Waitperson’s Race. Mon 7/11, 6-9 PM, 3300 N. Halsted, 773-883-0500, northalsted.com, $30, $25 in advance.
BenFest This family-friendly block party benefits the schools and parish of Saint Benedict. 7/15-7/16, Saint Benedict Church, 2215 W. Irving Park, 773-588-6484, benfest.com, $10, $5 before 8 PM.
Old St. Pat’s World’s Largest Block Party Two stages of live music, headliners TBA. 7/15-7/16, 5:30-10:30 PM, Old Saint Patrick’s Church, 700 W. Adams, 312-648-1021, worldslargestblockparty.com, $45, $40 advance, $70 two-day pass.
Windy City Ribfest Local and national purveyors of ribs, along with music and arts and crafts. 7/15-7/17, Friday 5-10 PM, Sat-Sun noon-10 PM, Windy City Ribfest, 4800 N. Broadway, 773-868-3010, chicagoevents.com, $5.
Lincoln Park Arts & Music Festival Almost 100 juried artists will round out this neighborhood festival. 7/16-7/17, noon-10 PM, 2300 N. Racine, chicagoevents.com, $7.
Chinatown Summer Fair Food, music, and entertainment, including a Lion Dance. Sun 7/17, 10 AM-8 PM, 2200 S. Wentworth, chicagoevents.com.
Celebrate Clark Street Rogers Park art and food festival with music on two stages. 7/23-7/24, 1-11 PM, 7200 N. Clark, 773-508-5885, celebrateclarkstreet.com, $5, $10 per family.
Fiesta del Sol Huge Pilsen street festival with food, rides, and lots of Latin music. 7/28-7/31, Thu 5-10 PM, Fri-Sat 11 AM-11 PM, Sun 11 AM-10 PM, 2200 S. Loomis, fiestadelsol.org.
Summer on Southport Food, an art show, and live music. 7/30-7/31, 11 AM-10 PM, 3700 N. Southport, southportneighbors.com $5.
Taste of Lincoln Avenue Lincoln Park’s longest block party, with 350 vendors, 40 bands on five stages—including Toad the Wet Sprocket, Sister Hazel, and Tom Chapin—and a kids’ carnival. 7/30-7/31, noon-10 PM, 2650 N. Lincoln, 773.868.3010, chicagoevents.com, $7-$10.
August
Evanston Lakeshore Arts Festival Visual art, live jazz, and classical music. 8/6-8/7, 11 AM-6 PM, Dawes Park, 1700 Sheridan, Evanston, 847-448-8260, cityofevanston.org.
Retro on Roscoe Antique vendors, bands, and a 25-chef chili cook-off, plus antique, classic, and muscle cars. 8/6-8/7, noon-6 PM, 2000 W. Roscoe, roscoevillage.org/Retro_On_Roscoe, $6.
Taylor Street Festa Italiana Little Italy festival with food and wine, street performers, a tribute to Bon Jovi, and more. 8/11-8/14, Thu-Fri 5-11 PM, Sat noon-11 PM, Sun noon-9 PM, 1500 W. Taylor, 630-443-8400, oshows.com, $7.
Chicago Korean Festival A celebration of Korean culture with tae kwon do demonstrations, a ssierum tournament from 2-7 PM both days, and a karaoke competition Saturday evening. Vendors will be on hand with the requisite kimchi, soju, and other food and drink options. 8/13-8/14, Sat noon-10 PM, Sun noon-9 PM, 3300 W. Bryn Mawr, starevents.com/events/chicago-korean-festival, $5.
Kite Festival The Chicago Fire Kite Team, America’s oldest competitive kite team, demonstrate their flying finesse at this free festival. In between the pro kiting demos, the field will be open to amateurs, and children’s kite building workshops will run from 11 AM to 2 PM. 8/13-8/14, 11 AM-4 PM, Chicago Botanic Garden, 1000 Lake Cook, Glencoe, 847-835-5440, chicagobotanic.org.
Northalsted Market Days Gloria Gaynor headlines the 30th iteration of this Boys Town festival. Maxine Nightengale, America’s Got Talent finalist Prince Poppycock, and others perform, plus 400 vendors selling art, crafts, food, and drink. 8/13-8/14, 11 AM-10 PM, 3656 N. Halsted, 773-868-3010, northalsted.com, $10, $7 before 5 PM.
Wrigleyville Summerfest Kids’ activities, music, and more, hosted by Resurrection Lutheran Church. 8/13-8/14, Sat noon-10 PM, Sun 10 AM-9 PM, Resurrection Lutheran Church, 3309 N. Seminary, explorechicago.org, $5.
Glenwood Avenue Arts Fest The tenth edition of the Rogers Park festival brings arts, crafts, an open-studio tour, live music on three stages, food, and more. 8/19-8/21, Fri 6-10 PM, Sat-Sun noon-9 PM, Glenwood Avenue Arts District, Glenwood & Morse, glenwoodave.org.
Chicago Air & Water Show If you work downtown, you’ll likely see some of this annual spectacle/military recruitment stunt/looming disaster, whether you want to or not. 8/20-8/21, 11 AM-4 PM, North Avenue Beach, 1600 N. Lake Shore, explorechicago.org.
Northside Summerfest North Center offers live music, food and drink, and arts and crafts. 8/20-8/21, Sat noon-10 PM, Sun 11 AM-9 PM, 4050 N. Lincoln, 773-665-4682, starevents.com/events/north-side, $5.
Ukrainian Festival Ukrainian crafts, music, food, and entertainment. 8/20-8/21, 12-10 PM, Smith Park, 2526 W. Grand, 773-252-1228, uccaillinois.org, $5.
The Boulevard This three-day event features artists, food and drink, and a lot of live music. Proceeds benefit St. Luke’s Lutheran Church. 8/26-8/28, Fri 5-10 PM, Sat noon-10 PM, Sun noon-9 PM, 3000 W. Logan, starevents.com/events/the-boulevard, $5.
Bucktown Arts Fest Art, poetry, music, theater, film, and food. 8/27-8/28, 11 AM-7 PM, Senior Citizens Memorial Playlot Park, 2238 N. Oakley, bucktownartsfest.com.
Taste of Greece Souvlaki, gyros, ouzo, and much more from Greektown restaurants. 8/27-8/28, noon-11 PM, 300 S. Halsted, 847-509-8050, greektownchicago.org.
Italian Village Ferrari Festival More than 60 vintage Ferraris on display, as well as music, food, wine, and activities for children. Proceeds benefit Children’s Memorial Hospital. Sun 8/28, 11 AM-2 PM, Italian Village, 71 W. Monroe, 312-332-7005, italianvillage-chicago.com, $30, free for kids under 6.
September
Chicago Fringe Festival Back for its second year, the Fringe gives around 50 uncommon performers and shows a chance to make it in the second city. 9/1-9/11, each show plays three to five times, at various venues in Pilsen, 773-428-9977, chicagofringe.org, $10.
Guiness Oyster Festival Live music, Guinness and Harp beers, and fresh oysters. Sat 9/3, 11 AM-11 PM, 2000 W. Roscoe, myfountainsquare.com/oyster, $7.
Festival de la Villita This festival, now in its 22nd year, celebrates Mexico’s independence from Spain with more than 100 food vendors, entertainment for kids, and a pavilion with lessons in traditional dancing. The 26th Street Mexican Independence Day Parade, which starts at noon on Sunday at 26th and Albany, ends at the festival. 9/9-9/11, 2600 S. Kostner, chicagoevents.com.
Windy City Wine Festival More than 270 wines from around the world, seminars, cooking demos, live music, and food. 9/9-9/10, Fri 4-10 PM, Sat 3-9 PM, Grant Park, Buckingham Fountain, Columbus & Congress., 847-382-1480, windycitywinefestival.com, $35, $27 advance, $10 designated driver, under 21 free with paying adult.
Lakeview East Festival of the Arts More than 150 juried artists, food and music, a sculpture garden, and more. 9/10-9/11, Sat 10 AM-6 PM, Sun 10 AM-5 PM, 600 W. Belmont, 773-348-8608, lakevieweastfestivalofthearts.com.
Lincoln Park Art Faire 100 vendors, food, live music, and an open-air studio with supplies for festivalgoers to make their own art. 9/10-9/11, 11 AM-6 PM, Lincoln Park Cultural Center, 2045 N. Lincoln Park West, 312-742-7726.
Renegade Craft Fair Put on by Renegade Handmade, this fair features crafters from all over the country. 9/10-9/11, 11 AM-7 PM, 2100 W. Divison, renegadecraft.com/chicago.
Wells Street Fall Fest This annual wine and food festival also has a juried fine art fair, plus live music. 9/10-9/11, Sat 10 AM-10 PM, Sun 10 AM-7 PM, 1450 N. Wells, chicagoevents.com, $5.
Chicago Gourmet The list of participants in this culinary celebration—including Stephanie Izard, Rick Bayless, Randy Zweiban—reads like a who’s who of local talent. The schedule hasn’t been announced yet, but expect seminars, demos, and lots of food and wine tastings. 9/23-9/25, Millennium Park, Michigan & Randolph, 312-742-1169, illinoisrestaurants.org, prices TBA.
Hyde Park Arts & Crafts Adventure Paintings, photography, dolls, pottery, jewelry, and more. 9/25-9/26, Sat 10 AM-6 PM, Sun 10 AM-5 PM, Hyde Park Shopping Center, 1526 E. 55th, community-2.webtv.net/asoa/hydeparkartscrafts. F