May

• May 21th-May 23th Chicago Mayfest
• May 29th-May 30th Belmont-Sheffield Music Festival

June

• June 5 Cuervo Games
• June 5-June 6 Do-Division Street Fest and Sidewalk Sale
• June 5-June 6 June Jam
• June 17 5K Traffic Jam
• June 10 Taste of Bryn Mawr
• June 11-June 13 Ribfest Chicago
• June 12 Market Day on Madison Street
• June 12-June 13 Andersonville Midsommarfest
• June 12-June 13 Old Town Art Fair
• June 12-June 13 Wells Street Art Festival
• June 18-June 20 Taste of Randolph Street
• June 18-June 20 The Raven
• June 20-June 31 Chicago Summerfest
• June 19 Takin' It To The Streets
• June 25-June 26th Chicago Pride Fest
• June 26th-June 27th Green Music Fest

July

• July 10-July 11 West Fest
• July 10-July 11 Rock Around the Block
• July 17-July 18 Sheffield Garden Walk & Festival
• July 24 Dragon Boat Race For Literacy
• July 24-July 25 Taste of Lincoln Ave.
• July 25 9th Anuual Arts Adventure
• July 28-August 1 NBGC Family Fest & Carnival
• July 31-August 1 Lincoln Park Arts Festival
• July 31-August 1 Summer on Southport

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August

• Aug 7-Aug 8 Northalsted Market Days
• Aug 7-Aug 8 Retro on Roscoe
• Aug 13-Aug 15 August Fest
• Aug 13-Aug 15 Ginza Holiday Festival
• Aug 14-Aug 15 Wrigleyville SummerFest 
• Aug 20-Aug 22Ukrainian Festival
• Aug 20-Aug 22North Side Summerfest
• Aug 21 Pearl Fest
• Aug 21-Aug 22 Glenwood Avenue Arts Fest
• Aug 28-Aug 29 Lake View Music Festival
• Aug 28-Aug 29 Taste of Greece

September

• Sep 10-Sept 11 Windy City Wine Festival
• Sep 11 79th Street Renaissance Festival
• Sep 11-Sept 12 Renegade Craft Fair
• Sep 11-Sept 12 Taste of Wells Street
• Sep 11-Sept 12 Lakeview East Fine Arts Festival
• Sep 18 Oyster Festival
• Sep 19 Historic Route 66 Classic Car Show
• Sep 24-Sept 26 Oktoberfest Chicago
• Sep 25-Sept 26 Hyde Park Arts & Crafts Adventure