I got this list from one of my friend. Really great one...
1. Chicago Gospel Music Festival
6/01 - 6/03
312-744-3315
Millennium Park (Randolph & Michigan), Chicago
2. CareFair-Art Festival
6/02
773-858-8091
4908 N. Damen Avenue, Chicago
3. Chalk Festival
6/02
773-562-4708
Oz Park, 2021 N. Burling Street, Chicago
4. Artworks On Walton
6/02 - 6/03
312-642-4907
930 N. Walton Street (State to Dearborn), Chicago
5. Belmont/Sheffield Music Festival
6/02 - 6/03
773-868-3010
3200 N. Sheffield Avenue, Chicago
6. Chicago Blues Festival
6/07 - 6/10
312-744-3370
Grant Park, 300 S. Columbus Drive, Chicago
7. Celebration-Party in the Plaza
6/08 - 6/10
773-665-4682
1633 N. Cleveland Avenue, Chicago
8. Chicago Cares Serve-a-thon
6/09
312-780-0800
Grant Park, Lower Hutchinson, Chicago
9. Fiesta Back of the Yards 2007
6/09 - 6/10
773-247-5100
1800 W. 47th Street (Ashland & Damen), Chicago
10. Annual Andersonville Midsommarfest
6/09 - 6/10
773-665-4682
5200 N. Clark Street, Chicago
11. Old Town Art Fair
6/09 - 6/10
312-337-1938
1763 N. North Park Avenue, Chicago
12. Printers Row Book Fair
6/09 - 6/10
312-222-3986
700 S. Dearborn Street, Chicago
13. Ribfest Chicago
6/09 - 6/10
847-677-8273
4000 N. Lincoln Avenue, Chicago
14. http://www.artworkschicago.com/
6/09 - 6/10
312-642-4907
1100 N. State, Rush & State, Chicago
15. Fiestas Puertorriquenas
6/12 - 6/17
773-292-1414
Humboldt Park, 1400 N. Sacramento, Chicago
16. Arts and Crafts Marketplace
6/13 - 6/15
South Canal Street from Jackson to Van Buren
17. Chicago SummerDance Festival
6/14 - 8/26
312-742-4007
Spirit of Music Garden, 601 S. Michigan, Chicago
18. Festa Pasta Vino
6/14 - 6/17
847-233-9966
2400 S. Oakley Avenue, Chicago
19. Blues on the Fox
6/15 - 6/16
630-844-4386
Illinois Fox River, Downtown Aurora
20. Highland Games & Scottish Festival
6/15 - 6/16
708-442-7293
Oak Brook Polo Grounds, 700 Oak Brook Road
21. Taste of Randolph Street
6/15 - 6/17
312-458-9401
1200 W. Randolph, (Randolph & Racine), Chicago
22. Festival 'A Taste of Greece'
6/15 - 6/17
630-834-7010
St. Demetrios Church, 893 Church Rd, Elmhurst
23. Aurora’s Downtown Alive! Festival
6/15 - 8/11
630-844-4731
Downer Place, River Street and Broadway, Aurora
24. Cantigny Sculpture & Fine Art Festival
6/16 - 6/17
847-444-9600
Cantigny Park, 1 S. 151 Winfield Road, Wheaton
25. Custer's Last Stand Festival of the Arts
6/16 - 6/17
847-328-2204
900 Chicago Avenue, Evanston
26. Concerts in the Park
6/20 - 8/08
630-963-5252
Wednesdays - Ty Warner Park, Westmont
27. Jammin' at the Zoo - Everclear
6/22
773-868-3010
Lincoln Park Zoo, 2200 N. Cannon Drive, Chicago
28. St. Josaphat Summerfest
6/22 - 6/24
773-327-8955
2311 N. Southport Avenue, Chicago
29. Berwyn's Cartopia
6/22 - 6/23
708-788-8100
Cermark Plaza, Berwyn
30. Calumet/Giles/Historic House Walk
6/23
312-225-2257
3100 S. Calumet Avenue, Chicago
31. Villa Park Summerfest 2007
6/23
630-834-8970
Cortesi Veterans Memorial Park, Villa Park
32. GLBT Pride Parade & Chicago Pride Fest
6/23 - 6/24
773-348-8243
3200 N. Halsted (Halsted & Belmont), Chicago
33. Chicago Summerfest in Lincoln Park
6/23 - 6/24
773-665-4682
2000 N. Clark Street, Chicago
34. Fountain Square Arts Festival
6/23 - 6/24
773-868-3010
Fountain Square, 1700 Sherman, Evanston
35. BAM! Belmont Arts and Music Festival
6/24 - 6/25
773-327-5123
Belmont Avenue (Damen to Leavitt) , Chicago
36. http://www.artworkschicago.com/
6/24 - 6/25
312-642-4907
900 N. Wabash (Delaware to Chestnut), Chicago
37. Jeff Fest
6/29 - 7/01
773-868-3010
Jefferson Park, 4850 N. Milwaukee, Chicago
38. Crystal Lake Gala Festival
6/29 - 7/01
815-334-7761
401 Country Club Road, Crystal Lake
39. Taste of Chicago
6/29 - 7/08
312-744-3370
Grant Park, 300 S. Columbus Drive, Chicago
40. Eyes to the Skies Balloon Festival
6/29 - 7/04
630-963-4281
Lisle Community Park, 1825 Short Street, Lisle
41. Chicago Country Music Festival
6/30 - 7/01
312-744-3315
Grant Park, 300 S. Columbus Drive, Chicago
42. Sandwich Freedom Days
6/30 - 7/01
815-786-8168
140 E. Railroad Street, Downtown Sandwich
43. Naperville Ribfest
6/30 - 7/04
630-357-9000
Knoch Park, 700 S. West Street, Naperville
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