Well to my new knowledge this is whats happening...so if your in the chicagoland area...come check it out! :D
*hopefully i didn't make any mistakes


May
23-Sept. 27: Randolph Street Market Festival
24: Bike the Drive, 300 E. Jackson Blvd.
27-30: Chicago Turkish Festival
28-31: Mayfest in Lincoln Square, 4700 N. Lincoln Avenue
30-31: Belmont-Sheffield Music Festival,3200 N. Sheffield Avenue
30-31: Do-Division Street Fest and Sidewalk Sale, Ukrainian Village, 2000 W. Division Street
June
5-6: 57th Street Art Fair, Hyde Park, 5700 S. Kenwood Avenue
5-7: The Raven: Experience the Magic of Ravenswood, 4701 N. Ashland Avenue
6-7: Chicago Gospel Music Festival, Millennium Park, 201 E. Randolph Street
6-7: Chicago Tribune Printers Row Lit Fest, 700 S. Dearborn Street
11-Aug. 23: Chicago SummerDance Festival
12-14: Chicago Blues Festival, Grant Park, 300 S. Columbus Drive
12-14: Fiesta Back of the Yards 2009
12-Aug. 30: Movies in the Parks
12-14: Party at St. Mike's
12-14: Ribfest Chicago
13: Humboldt Park Art Fair
13-14: Andersonville Midsommarfest, 5200 N. Clark Street
13-14: Old Town Art Fair, 1763 N. North Park Avenue
13-14: Wells Street Art Festival, Old Town, 1300 N. Wells Street
14: Q101 Block Party
15-21: Fiesta Puertorriquenas
18-20: Steamboat Sports Festival, Riverfront Festival Park, Peoria, IL
19-21: Naper Day, Naperville Settlement, Naper, IL
19-21: Chicago Peace Fest
19-21: Close Up 2 Smooth Jazz Festival
19-21: Festa Pasta Vino, Little Tuscany, 2400 S. Oakley Avenue
19-21: St. Josaphat Summerfest
19-21: Taste of Greece on LaSalle Street Festival
19-21: Taste of Randolph Street, West Loop, 900 W. Randolph Street
20: Puerto Rican Day Parade, Grant Park, 300 E. Balbo Street
20-21: BAM! Belmont Arts and Music Fest, Roscoe Village, Belmont and Damen Avenue
20-21: Chicago Summerfest, Lincoln Park, 2000 N. Clark Street
26-27: Chicago Pride Fest
26-28: Taste of Joliet, Joliet Memorial Stadium, Joliet, IL
26-28: Chicago Soul Music Festival, West Loop 1501 W. Randolph Street
26-July 5: Taste of Chicago, Grant Park, 300 S. Columbus Drive
28: Pride Parade, Lakeview, Halsted and Belmont
July
1-5: Taste of Lombard, Lombard, IL
3-4: Taste of Downtown Springfield and Bicentennial Celebration, Springfield, IL
3-5: African-Caribbean International Festival of Life
8-10: Thai Festival Chicago
9: Bastille Day 5K Run, Walk and Block Party, West Loop, 1100 W. Jackson Blvd.
10-12: Irish American Heritage Festival, North Park, 4626 N. Knox Avenue
10-11: BenFest, Roscoe Village/Northcenter, 2215 W. Irving Park Road
10-11: Old St. Pat's World's Largest Block Party, West Loop, 650 W. Madison Street
10-12: Chicago Tribune Magnificent Mile Art Festival
11: 'I Have a Vision' Community Gospel Festival
11-12: Chicago Folk and Roots Festival
11-12: Rock Around the Block, Lakeview, 3200 N. Lincoln Avenue
11-12: St. Andrew's Greek Festival
11-12: West Fest 2009
12-14: Ribfest Chicago
14-Aug. 25: Free! Outdoor Film Festival in Grant Park
17-19: Pitchfork Music Festival
18-19: Sheffield Garden Walk and Festival, Sheffield/DePaul, 2200 N. Sheffield Avenue
19: Chinatown Summer Fair, Chinatown, 2200 S. Wentworth
25: Venetian Night, Monroe Harbor, 100 S. Lake Shore Drive
25-26: Taste of Lincoln Avenue, Sheffield/DePaul, 2400 N. Lincoln Avenue
25-26: Wicker Park Fest. Bucktown/Wicker Park, 1300-1550 N. Milwaukee Avenue
26: Celebrate Clark Street Festival
30-Aug. 2: Fiesta del Sol, Pilsen, 1400 W. Cermak Road
31-Aug. 2: Gold Coast Art Fair, River North, 700 N. LaSalle Street
31Aug.2: Taste of Orland Park
August
1-2: Northalsted Market Days, Boystown, 3500 N. Halsted Street
1-2: Retro on Roscoe, Roscoe Village, 2000 W. Roscoe Street
2: Belize Day in the Park
7-9: Ginza Holiday
7-9: Lollapalooza, Grant Park, 500 S. Columbus Drive
8: Bud Billiken Parade and Picnic, Oakland/Full Park, 3900 S. King Drive
8-9: Korean Street Festival, Sauganash, 3200 W. Bryn Mawr Avenue
8-9: New! Lincoln Park Arts and Music Festival, 2200 N. Racine Avenue
8-9: Wrigleyville SummerFest, 3309 N. Seminary Avenue
12: Taste of Peoria, Riverfront Festival Park, Peoria, IL
14-23: Illinois State Fair, Illinois State Fairground, Sangamon & Peoria Rd., Springfield. (217) 782.6661
14-16: Edison Park Fest
14-16: North Side Summerfest
14-16: New! Chicago Ribs 'n' Soul Festival
15: Croatian Fest
15-16: Armenian Fest
15-16: Chicago Air & Water Show, North Avenue Beach, 1600 N. Lake Shore Drive
15-16: Chicago Carifete
15-16: New! Green Music Fest
21-23: 60th Annual Greek Festival
21-23: Glenwood Avenue Arts Fest
22-23: Lake View Music Fest, Wrigleyville, 3600 N. Sheffield Avenue
29-30: Bucktown Arts Fest, 2238 N. Oakley Avenue
29-30: Taste of Greece 2009, Greektown, 100-400 S. Halsted Street
29-30: !Viva! Chicago Latin Music Festival

September
4-6: Chicago Jazz Festival, Grant Park, 300 S. Columbus Drive
4-7: African Festival of the Arts, Washington Park, 5100 S. Cottage Grove Avenue
4-7: Taste of Polonia
5-6: Bash on Wabash, South Loop, 1300 S. Wabash Avenue
7: Labor Day Parade/Picnic, Downtown Peoria/Festival Park, Peoria, IL
11-13: 89th Annual German-American Festival, Lincoln Square, 4700 N. Lincoln Avenue
12-13: Celtic Fest Chicago
12-13: Groovin' on the Grove Festival
12-13: Renegade Craft Fair
12-13: Ukrainian Village Fest
13: 26th Street Mexican Independence Day Parade, Pilsen, 3100 W. 26th Street
13-14: Wells Street Crush, Music and Comedy Fest, Old Town, 1330 N. Wells Avenue
25-27: Oktoberfest

um......what?

That's...a lot of events.

OMG SO MANY EVENTS

I live in Chicagoland but...
TL;DR

wow so many events!!!

I went to lollapalooza... was awesome, although chicago has some shitty bud