Art Chicago

222 W Merchandise Mart Plz, Chicago, IL 60654 312-527-4141

Description: Although Art Chicago graced Grant Park each year for a decade, it moved to the Merchandise Mart in 2006, with much success. About 200 galleries from around the US and the world participate, showcasing visual arts from established and emerging artists alike. Highlights of the 2007 event include video installations, an art bookstore presented by Powell's of Chicago, an exhibition of works created by students from art schools around the country (Cranbrook Academy of Art, Rhode Island School of Design and the California Institute of the Arts, among others), a great variety of seminars and symposiums on all aspects of art (creating it, selling it, green techniques), and even art activities for kids.
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Belmont-Sheffield Music Festival

N Halsted at N Clark, Chicago, IL 60614 773-584-6642

Description: A city so well-known for its music whether it be soulful blues, soothing jazz, or pumping house music, Chi-town is no stranger to music festivals. Get some of the real representation of this city's musical vibe at the Belmont-Sheffield Music Festival. This pocket in the Lakeview neighborhood is home to in-the-know young adults, and it features hip and trendy boutiques and eateries, most of which get in on the festival fun. Eat and soak up what's showcased during this celebration of all things music.
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Bike the Drive

Columbus & Jackson, Lake Michigan Shorefront, Chicago, IL

Description: Chicago's beautiful Lake Michigan shorefront becomes extra beautiful from 5:30am to 10am on May 24. Why? Thanks to Bank of America, no cars will be allowed on Lake Shore Drive at that time! Bikers take over the gorgeous area, traffic-free, on this day only. From pros to families, all ages can bike the ever-growing event. Post-ride, enjoy a festival with an all-you-can-eat pancake brunch by local brewery, Goose Island. Booths and activities geared for families are slated, as well as educational talks on the Active Transportation Alliance.

* As added incentive, 10Best readers can claim a $5 discount on registration packages by entering TEN2A5 as an online coupon code, thanks to the Active Transportation Alliance.
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Chicago Blues Festival

331 E Randolph St, Chicago, IL 60601 312-744-3315

Description: The soulful Windy City puts on annual Blues Festival with as big of names as ever including, yes, B.B. King. Along with King: James Cotton, Buckwheat Zydeco and Koko Taylor will belt their blues amongst many of local favorites. Grab a drink and spill your guts to those around you; that's what has kept this festival growing. From its debut year with nearly 165,000 in attendance to last year's 800,000, it boasts plenty of Chicagoan pride.
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Chicago Festa Pasta Vino

2400 S Oakley Ave, Chicago, IL 60608-4902

Description: "Chicago, Chicago, that tottlin' town..." - Frank and company would surely support this Italian favorite. Those planning to attend one of the Midwest's oldest Italian Festivals should prepare to feast on this city's most delectable Italian eats and vino. And although food comes first, working it out to live music and learning a thing or two from the old school celebrators ... well that, friends, is amore!
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Chicago Gay Pride Parade

N Halsted, between Addison & Grace, Chicago, IL 60614

Description: Chicago's "Boystown" neighborhood comes alive with color, music, dancing and of course, pride. Expect the unexpected - costumes of all sorts, music of all genres, rainbows everywhere and even major political figures in attendance. Although the parade "officially" begins at 11am, the party figures to last no less than 24 hours. Word of the wise, take public transportation; driving in this neighborhood is not possible this day.
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Chicago Gospel Music Festival

331 E Randolph St, Chicago, IL 60601 312-744-3315

Description: If you're a fan of gospel music, with its signature energy and vibrancy, you'll definitely want to head to Grant Park for this non-stop music extravaganza. Three stages host a wealth of performers who turn up the showmanship and the vocals to glorify their Creator and to establish a sense of community among spectators. An art fair and plenty of family-friendly activities up the ante on fun and camaraderie.
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Chicago Pizza Fest

Racine & Fullerton, Chicago, IL 60614

Description: Pizza lovers united? This is your festival! Even New Yorkers have to admit the Chicago Pizza Fest is simply delicioso. Showing off one of the city's most notable dishes, Chicago looks for its best pizza-makers. Take advantage and enjoy the live music while tasting the heavenly pies! Watch as some of the region's best chefs compete for the Chicagoland's Best Pizza Award. Judging takes place on Saturday at 3pm.
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Chicago Tribune Printers Row Book Fair

Dearborn St at Polk St, Chicago, IL 60601

Description: The energy of Printers Row's history comes to life annually for the Book Fair, this year on its 23rd year. Also known as the Midwest's largest outdoor literary event (it's free, too!), The Chicago Tribune Printers Row Book Fair is THE place to find nearly 200 book vendors, a grand display of authors with plenty of presentation programming and meet & greet opportunities.
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Christkindlmarket Chicago

50 W Washington St, Chicago, IL 60602

Description: Daley Plaza is the center of all Chicago's holiday festivities, morphing into a haunted village for Halloween, and into various international markets throughout the summer. For the Christmas season, it's transformed into a traditional German-style market. Vendors offer all sorts of arts and crafts from around the world, and restaurants and caterers provide the best German food, beer and wine. The event is also graced with a visit from the Christkindl herself (she's a gift-bearing fairy, similar to Santa Claus), direct from Nuremberg. Other highlights include the official City of Chicago Holiday Tree Lighting, and the Children's Lantern Parade.
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Grant Park Music Festival

331 E Randolph St, Chicago, IL 60601 312-744-3315

Description: Not just a one-weekend event, this festival runs throughout the summer, from June til August. Free concerts highlight a wealth of classical music, from Brahms and Chopin to Beethoven and more; other works applaud Hungary, Thailand, Spain, and other nations. Notable vocalists and pianists perform with the orchestra and the chorus as well. Millennium Park's Jay Pritzker Pavilion, site of the concerts, is the official home of Grant Park Orchestra and Chorus.
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Long Grove Strawberry Festival

307 Old Mchenry Rd, Long Grove, IL 60047 847-634-0888

Description: Watch the tiny cobblestones streets of beautiful, historic Long Grove Village fill up with nearly 50,000 visitors ready to gorge on fresh berries. More than just strawberries, expect to find delectable sweets, chocolate of all kinds, a beer and brat stand, and even a classic car show. The specialty boutiques that make up this village will all vie for attention with their own specialties and sales. Be sure to come hungry.
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Onion City Experimental Film and Video Festival

5243 N Clark St, Chicago Filmmakers, Chicago, IL 60640

Description: Onion City celebrates experimental filmmaking like no other festival. These short pieces, mostly ranging from about 3 to 30 minutes, challenge contemporary views of the moving image and offer insight into the evolution of modern day cinema. Some are simply designed as visual treats, others as cutting-edge features, but all are fascinating. Most screenings are at the Chicago Filmmakers cinemas, but the opening night festivities take place at the Gene Siskel Film Center (164 N State St).
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Ravinia Festival

Ravinia Park Rd and Green Bay Rd, Highland Park, IL 60035

Description: The Ravinia Festival has been a favorite occasion for music concerts for a century now! It hosts famous act after famous act, and more than 100 events take place from June through September, including classical, pop, jazz, music theater, dance, world, and kids programming. Locals know to go for the grass seats and to pack an oversized picnic. Seated tickets for big events sell out quickly, but the grassy knoll is almost more welcoming, come rain or shine.
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SummerDance

601 S Michigan Ave, Spirit of Music Gardens in Grant Park, Chicago, IL 60604 312-742-7529

Description: Summertime is the best time of the year to discover a new skill. Luckily, this yearly event can help you learn to lindy hop or allow you to pick up some bachata or ballroom moves. The city's free festival runs for 11 weeks in the summer, and professional instructors give one-hour lessons. After the tutorial ends, stay for two hours of live music and practice what was just taught.
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Third Thursdays: The Best of Looptopia

Various venues around The Loop, Chicago, IL

Description: A wildly popular celebration of the arts, the original Looptopia brought together a huge assortment of performers, from bands and choral groups to ballet and break dancers to poets and mimes to visual art exhibitions that went on until the wee hours for just one night. No longer an all night event (but just as fun) the organizers decided to spread the festivities out from May through September. On the 3rd Thursday of each month the event takes place at various venues through the Loop.
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Wells Street Art Festival

Wells St and North Ave, Chicago, IL 60610 773-584-6625

Description: Chicago's Old Town neighborhood celebrates art, music, and local flavor. Listen to the jazz and even a Beatles tribute while you peruse the oil paintings, ceramics and jewelry. Talk to the artists and put your bid on a favorite by entering the silent auction. Old Town's charming one-of-a-kind shops are sure to highlight their best this weekend, be sure to visit the Spice Shop and the many floral shops that line Wells Street, some of the best Chicago has to offer.
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