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. 
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.
Belmont-Sheffield Music Festival Trippin Billies and Wedding Banned headline.
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.
June
Mayfest Chicago You’ll find good old-fashioned gemütlichkeit and an actual maypole at this Lincoln Square festival. 
Beer Hoptacular Craft brewers talk up and sample out their wares in three sessions, each with food pairings provided by Whole Foods.
Eastside Millennium Art Festival 150 artists on three blocks, with live music and food.
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.
June Jam Family-friendly street fair with music, kid-oriented games and activities, and food.
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.
Sketchbook Collaboraction’s annual performing arts festival features short original works (seven minutes or less), plus live music and visual art.
Taste of Bryn Mawr Food samples and sales on merchandise from participating Edgewater businesses.
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.
Andersonville Midsommarfest Celebrating Andersonville’s Swedish heritage with eats and entertainment.
Chicago Botanic Garden Wine Festival More than 200 wines, along with cooking demos, food vendors, wine seminars, and live music.
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.
Humboldt Park Art Fair Put on by emerging artists for emerging artists, this year’s fair features dozens of artists and musical acts.
Old Town Art Fair Juried show of more than 260 artists, plus live music and activities for kids.
Wells Street Art Fair One of the city’s bigger art fairs, with music from Trippin Billies and Rock Candy.
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.
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.
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.
Grant Park Music Festival Guest conductors and instrumentalists season the Grant Park Orchestra’s renditions of everything from Vivaldi to Dvorak.
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.
Bronzeville Cultural Festival Includes a book fair, film festival, and opening gala with live music and an awards ceremony.
SummerDance Concerts in a variety of genres preceded by free dance lessons in the relevant style.
Festa!Pasta!Vino! Italian Street Festival Italian festival with live entertainment, food from local restaurants, and imported merchandise.
Midsummer Festival Another Scandinavian solstice festival, with live music, arts and crafts, and activities for kids.
Scottish Festival & Highland Games Celebration of Scottish culture including bagpipe music, Highland dancing, Scotch whisky tastings, rugby sevens, live music, and more.
Cantigny Art Festival Annual art fair with more than 150 vendors.
Custer’s Last Stand Art festival with 30 food vendors, commercial stands from 150 local businesses, and live music.
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).
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.
Bloomington Gold Corvette Show National Corvette show, now in its 38th year.
Chicago Arabesque Food, handicrafts, music, and dance from across the Middle East.
Cans Music Fest Headliners this year are Coolio and Wang Chung.
Chicago Pride Fest Arts and crafts, food, and live entertainment on two stages, including performances by Sixteen Candles and Wedding Banned.
Long Grove Strawberry Festival Strawberries, chocolate-dipped strawberries, strawberry baked goods, and more.
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.
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).
Chicago Summerfest Art show, family area, and live music.
Fountain Square Art Festival Juried fine arts fair with more than 200 artists.
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).
Pride Parade The 41st annual parade travels north on Halsted from Belmont to Broadway, south on Broadway, and east on Diversey to Cannon.
July
Naperville Ribfest Sammy Hagar, the Charlie Daniels Band, LeAnn Rimes, and Blue Oyster Cult headline. Sixteen rib vendors are promised, along with fireworks on the fourth.
Bastille Day 5K Run, Walk, and Block Party After the run/walk, there’s a block party with food, beer, and live music.
BenFest This family-friendly block party to benefit the schools and parish of St. Benedict has a lineup that includes How Far to Austin, Infinity, Open to Suggestions, Eric Howell’s Greatest Hitch, and Send in the Clones.
Boulevard Bash This three-day event features artists, food and drink, and a lot of live music. Proceeds benefit St. Luke’s Lutheran Church.
Great Performers of Illinois A 7,000-square-foot “urban corn maze,” chain-saw carvings, Abe and Mary Todd Lincoln impersonators, wine tasting, square dancing, and more. A Sunday evening concert features Rachel Barton Pine, violinist and recipient of this year’s Great Performer of Illinois award.
Old St. Pat’s World’s Largest Block Party Two stages of live music, with the Barenaked Ladies headlining on Friday night.
Jeff Fest Live music at this Jefferson Park neighborhood celebration includes Rock Candy, Libido Funk Circus, and Too White Crew. There’s also a bike parade and classic car show.
Rock Around the Block Stretched over four Lakeview blocks—which center around the intersection of Belmont, Lincoln, and Ashland—this festival claims to have “thirty of the Windy City’s best bands.”
Roscoe Village Burger Fest Formerly Belmont Arts and Music (BAM!) Festival, this neighborhood event has been retooled into a festival that “celebrates the burger.” Food and drinks are for sale; headliners this year are Gin Blossoms and 10,000 Maniacs.
Halsted Tastes Better All-you-can-eat chow from North Halsted neighborhood restaurants. There’s also live music and a Waitperson’s Race.
Festival of the Lakes Polka, pontoon rides, and beer gardens are some of this festival’s assets. So are its opening night musical acts: En Vogue and Boyz II Men. Various locations, Hammond, Indiana.
Windy City Ribfest Last year, this festival was inaugurated in Union Park; this time around it’s in Uptown, and still includes tons of ribs and performers like Tonic, Canasta, and Sister Hazel.
Evanston Ethnic Arts Festival Flags of more than 100 nations surround this lakefront festival, which includes live music, dance, juried artwork, and food.
Sheffield Garden Walk Self-guided tours of more than 100 gardens, plus food and music. Headliners this year are Rusted Root and Cowboy Mouth.
Southside Neighborhood Gospel Festival Gospel musicians, food, a senior pavilion, and a kids’ zone.
Taste of River North Neighborhood restaurants, live music, and local artists and merchants.
Chinatown Summer Fair Live music, food, crafts, a petting zoo, and more; a lion dance procession starts at 12:45 PM.
Dearborn Garden Walk Tours of more than 20 gardens, live jazz and classical performances, and a narrated architectural tour.
Edgebrook Festival Arts and crafts festival with live music, a beer garden, and a kids’ corner.
Pierogi Fest Vendors come from Cleveland and Canada, the chamber of commerce calls itself the Pierogatory, and even the dogs don babushkas in honor of the humble Polish dumpling.
Celebrate Clark Street Rogers Park art and food festival with music on two stages.
Taste of Lincoln Avenue Lincoln Park’s longest block party, with 350 vendors, 40 bands on five stages, and a block-long kids’ carnival.
Neighborhood Boys and Girls Club Family Fest Carnival rides, games, a $10,000 jackpot drawing, and beer.
Fiesta del Sol Huge Pilsen street festival with food, rides, and lots of Latin music.
Chicago Luxury Ice Cream Festival Chefs, creameries, and pastry artists create unusual ice creams for sampling.
Ghanafest Billed as the “largest and most spectacular Ghanaian cultural exposition of its kind in the diaspora,” with arts, crafts, traditional foods, and more.
Lincoln Park Arts and Music Festival Visual art and live music; proceeds benefit the Lincoln Park Chamber of Commerce.
Summer on Southport Food, an art show, and live music.
August
Serbfest Traditional Serbian food, dancing, and music.
Taylor Street Festa Italiana Italian festival with live entertainment, food from local restaurants, imported merchandise, and a Sunday Mass.
Evanston Lakeshore Arts Festival Visual art, plus live jazz and classical music.
Northalsted Market Days Joan Jett and the Blackhearts headline this year; there’s also music from Jon Secada, Jennifer Holliday, and American Idol finalist Blake Lewis, and 400 vendors sell art, crafts, and food.
Retro on Roscoe Antique vendors, bands, and a 25-chef chili cook-off, plus antique, classic, and muscle cars.
Veggie Fest Food vendors, cooking demos, health talks, and live music to demonstrate “the many spiritual, physical, mental and social benefits of being vegetarian.”
World of Faeries Festival There’s live music, but the costumed patrons are the main attraction.
Augustfest Live music, carnival rides, food, and more.
Ginza Holiday Midwest Buddhist Temple celebrates an array of Japanese cultural traditions, including ikebana (flower arrangement), various martial arts, taiko drumming, calligraphy, and more. Food, such as a grilled chicken teriyaki dinner, is available, and so is Japanese beer. On Sat 8/14, 8 PM, Yoko Noge and the Japanesque Band performs.
Chicago Air & Water Show If you work downtown, you’ll probably see some of this annual spectacle/military recruitment stunt/disaster waiting to happen, whether you want to or not.
Wrigleyville Summerfest Food, kids’ activities, music, and more, hosted by Resurrection Lutheran Church.
Riverfest Express Craft show, trolley rides, car show, fireworks, and live entertainment including Parrothead Express and the Neverly Brothers.
Glenwood Avenue Arts Festival Arts, crafts, an open-studio tour, live music, food, and more.
Gold Coast Art Fair 450 juried artists, food, and live music. This year the festival moves to new digs in Grant Park, at the corner of Monroe and Lake Shore Drive.
Northside Summerfest North Center offers live music, food and drink, and arts and crafts.
Windy City Rodeo
Chicago Carifete Caribbean festival featuring live calypso, soca and reggae, food and drink, and a parade.
Ukrainian Festival Ukrainian crafts, music, food, and entertainment.
Chicago Dancing Festival Three nights of events—like lectures and performances by members of the Joffrey Ballet and Lar Lubovitch Dance Ensemble, among other troupes—make up this acclaimed annual festival, which is free but requires reservations. Locations vary, and include the Harris Theater and Pritzker Pavilion, both in Millennium Park, and the Museum of Contemporary Art.
Bucktown Arts Fest Art, poetry, music, theater, film, and food.
Taste of Greece Souvlaki, gyros, ouzo, and more from Greektown restaurants.
Italian Village Ferrari Festival Sixty vintage Ferraris on display, as well as music, food, wine, and activities for children. Proceeds benefit Children’s Memorial Hospital.
September
Bash on Wabash South Loop neighborhood festival with art, food, a “corn bags tournament,” and live music.
Festival de la Villita This festival celebrates Mexico’s independence from Spain with more than 100 food vendors, entertainment for kids, and a dance pavilion with lessons in traditional dancing. The 26th Street Mexican Independence Day Parade, which starts at noon at 26th and Albany on Sunday, ends at the festival.
German American Fest A parade Saturday (starting at 2 PM at 4000 N. Lincoln) commemorates the life of Baron Friedrich von Steuben, who volunteered to serve under George Washington during the Revolutionary War. At the festival, expect music, dancing, and copious amounts of German food and beer.
Windy City Wine Festival More than 200 wines from around the world, seminars, cooking demos, live music, and food.
Auburn-Gresham 79th Street Renaissance Festival Festivities, food, and entertainment.
Lakeview East Festival of the Arts More than 150 juried artists, food and music, a sculpture garden, and more.
Lincoln Park Art Faire 100 vendors, food, live music, and an open-air studio with supplies for festivalgoers to make their own art.
Renegade Craft Fair Put on by Renegade Handmade, this fair features crafters from all over the country.
Wells Street Fall Fest Formerly “Wine Crush in Old Town” and then “Crush, Music, & Comedy Fest,” this annual wine and food festival introduces a fair of juried fine artists this year. There’s also live music.
Graue Mill’s Cornfest At this “old-fashioned family picnic,” barbecue is served alongside roasted corn and homemade pie; a German band provides the music.
Lebowski Fest Abide a while at this year’s Lebowski Fest events: on Friday, Portage Theater screens the film The Big Lebowski at 8 PM, and on Saturday, Diversey Rock and Bowl offers bowling, trivia, costumes, and more.
Naperville Wine Festival More than 200 wines, along with cooking demos, food vendors, wine seminars, and live music.
Guiness Oyster Festival Live music, Guinness and Harp, and fresh oysters.
Oktoberfest Chicago Beers, bands, and bratwurst.
Chicago Gourmet The list of participants in this culinary celebration—including Shawn McClain, Graham Elliot Bowles, Gale Gand, and a few dozen more—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.
Edgewater GRalley An official event of the World Music Festival, this street fest includes music, food, a silent auction, and an “Artists’ Alley.”
Eli’s Cheesecake Festival Cooking demos, cheesecake-eating contests, and music by Karen Hart Band, June’s Got the Cash, Band on the Run, and more. There’s also a classic car show on Sunday.
Hyde Park Arts & Crafts Adventure Paintings, photography, dolls, pottery, jewelry, and more.