Click the festival below for more informationCity AreaDates
Chicago Memorial Day ParadeLoopMay 27
Greektown Mediterranean Wine FestivalGreektownMay 27 - 28  
Randolph Street Market FestivalNear West SideMay 27 - 28  
Belmont-Sheffield Music Festival LakeviewMay 27- 28
Maifest ChicagoLincoln SquareJune 1 - 4 
Chicago Gospel Music FestivalMillennium ParkJune 2 - 3
Do DivisionWest TownJune 2 - 4
Taste of Little Village: Flavors of MexicoLittle VillageJune 2 - 4
Lincoln Park Greek FestLincoln ParkJune 2 - 4   
57th Street Art FairHyde ParkJune 3 - 4 
Wingout ChicagoOld TownJune 3 - 4 
Hyde Park Brew FestHyde ParkJune 3 - 4 
Andersonville MidsommarfestAndersonvilleJune 9 - 11 
Ribfest ChicagoNorth CenterJune 9 - 11
Chicago Blues FestivalMillennium ParkJune 9 - 11
Spring Awakening Music FestivalUniversity VillageJune 9 - 11  
Vegan Drink FestGrant ParkJune 10
Green Music FestWicker ParkJune 10 - 11  
Printers Row Lit FestPrinters RowJune 10 - 11  
Pilsen Food Truck SocialPilsenJune 10 - 11  
Wells Street Art FestivalOld TownJune 10 - 11
Old Town Art FairOld TownJune 10 - 11
6 Corners BBQ FestPortage ParkJune 10 - 11
Oakley Festa Pasta VinoLower West SideJune 16-18
Taste of RandolphWest LoopJune 16-18
Craft Brews at the ZooLincoln Park ZooJune 16 - 17 
Fiestas Puertorriqueñas West TownJune 17
Chicago Pride FestEast LakeviewJune 17 - 18
Custer FairEvanstonJune 17 - 18
Gold Coast Art FairGrant ParkJune 17 - 18  
Chicago Ale FestGrant ParkJune 23 - 24  
Old St. Pat's Block PartyWest LoopJune 23 - 24  
Logan Square Arts FestLogan SquareJune 23 - 25  
Greek Festival on Gold CoastGold CostJune 23 - 25  
Country LakeShake Music FestivalNortherly IslandJune 23 - 25  
Fountain Square Art FestEvanstonJune 24 - 25
Chicago Food Truck FestChinatownJune 24 - 25
Evanston Chamber Artisan SummerFestEvanstonJune 24 - 25
Ravenswood on TapAndersonvilleJune 24 - 25
Mamby On The BeachOaklandJune 24 - 25
Chicago Taco & Tequila Fest Jackson ParkJune 24 - 25
Randolph Street Market FestivalNear West SideJune 24 - 25  
Pride ParadeEast LakeviewJune 25
Windy City Ribfest in Uptown UptownJune 30 - July 2
Chosen Few Picnic: House Music FestivalJackson ParkJuly 1 - 2  
African/Caribbean International Festival of LifeNear West SideJuly 1 - 4 
Fourth of July Fireworks at Navy PierNavy PierJuly 4
Taste of ChicagoGrant ParkJuly 5 - 9 
Square Roots FestivalLincoln SquareJuly 7 - 9 
Millennium Art FestivalMillennium ParkJuly 7 - 9 
Ruido FestUniversity VillageJuly 7 - 9 
West FestWest TownJuly 7 - 9  
Irish American Heritage FestivalMayfairJuly 7 - 9 
Chicago Margarita FestivalSouth ShoreJuly 8 - 9 
Roscoe Village Burger FestRoscoe VillageJuly 8 - 9 
North Shore Festival of ArtsSkokieJuly 8 - 9 
Taste of Park RidgePark RidgeJuly 13 - 15
BenFestNorth CenterJuly 14 - 16
Windy City SmokeoutRiver NorthJuly 14 - 16
Pitchfork Music FestivalNear West SideJuly 14 - 16
Chicago Open Air Music FestivalToyota ParkJuly 14 - 16
Chicago Yacht Club Race to MackinacNavy PierJuly 15 
The Silver Room Block PartyHyde ParkJuly 15 
Southport Art FestLakeviewJuly 15 - 16
Colombian FestKelvyn ParkJuly 15 - 17
Chinatown Summer FairChinatownJuly 16
Dearborn Garden WalkNear North SideJuly 16
artfest Michigan AvenueMag MileJuly 21 - 23   
Taste of River NorthRiver NorthJuly 21 - 23 
Sheffield Music Festival & Garden Walk  Lincoln ParkJuly 22 - 23
Chicago Craft Beer Festival Lincoln ParkJuly 22 - 23
Fiesta del SolLower West SideJuly 27 - 30 
Sidewalk SaleAndersonvilleJuly 28 - 30 
Bantu FestHyde ParkJuly 29 
Tour de FatNortherly IslandJuly 29 
Taste of Lincoln Avenue Lincoln ParkJuly 29 - 30
Wicker Park FestWicker ParkJuly 29 - 30  
Randolph Street Market FestivalWest LoopJuly 29 - 30
LollapaloozaGrant ParkAugust 3 - 6  
Jeff FestJefferson ParkAugust 4 - 6
Edge FestEdgewaterAugust 5 - 6
Taste of AndersonvilleAndersonvilleAugust 9
Chicago Hot Dog FestLincoln ParkAugust 11 - 13
Ginza Festival ChicagoOld TownAugust 11 - 13
Retro on RoscoeRoscoe VillageAugust 11 - 13
Bud Billiken ParadeBronzevilleAugust 12
Northalsted Market DaysEast LakeviewAugust 12 - 13 
Clark After DarkRiver NorthAugust 17  
Festa ItalianaUniversity VillageAugust 18 - 20
Edison Park FestEdison ParkAugust 18 - 20 
Glenwood Avenue Arts FestRogers ParkAugust 18 - 20 
Windy City CarnivalHyde ParkAugust 19 
Oak Park Microbrew ReviewOak ParkAugust 19 
Chicago Air & Water Show LakefrontAugust 19 - 20 
Taste of Greektown GreektownAugust 25 - 27
Skokie Backlot BashSkokieAugust 25 - 27
Bucktown Arts FestBucktownAugust 26 - 27
Randolph Street Market FestivalNear West SideAugust 26 - 27
Chicago Fringe FestivalJefferson ParkAugust 30 - September 10  
Chicago Jazz FestivalGrant ParkAugust 31 - September 3 
Great American Lobster Fest Navy PierSeptember 1 - 3 
North Coast Music FestivalNear West SideSeptember 1 - 3 
African Festival of the ArtsWashington ParkSeptember 1 - 4
Taste of PoloniaJefferson ParkSeptember 1 - 4 
Windy City Wine FestivalGrant ParkSeptember 8 - 9
Throwback Music Festival Gladstone ParkSeptember 8 - 10
German-American OktoberfestLincoln SquareSeptember 8 - 10
Rocktober BeerfestNear West SideSeptember 8 - 10
Ukrainian Village FestUkranian VillageSeptember 9 - 10
Festival of ArtsEast LakeviewSeptember 9 - 10
Streets Alive! FestEvanstonSeptember 10
Mexican Independence Day ParadeLittle VillageSeptember 10
EXPO ChicagoNavy PierSeptember 13 - 17
Riot Fest & CarnivalDouglas ParkSeptember 15 - 17    
St. Benedict’s OktoberfestGold CostSeptember 15 - 17    
Ravenswood ArtWalkRavenswoodSeptember 16 - 17
Sam Adams' Lakeview Taco Fest LakeviewSeptember 16 - 17
West Loop Art FestWest LoopSeptember 16 - 17 
Chicago GourmetMillennium ParkSeptember 22 - 24
Logan Square Food Truck SocialLogan SquareSeptember 22 - 24
AAHH! Fest by CommonNear West SideSeptember 23 - 24
Randolph Street Market FestivalNear West SideSeptember 23 - 24
Edgewater Arts Festival EdgewaterSeptember 23 - 24
Oktoberfest Chicago at St. Alphonsus  LakeviewSeptember 29 - October 1
Fulton Market Harvest FestFulton MarketSeptember 29 - October 1
Apple FestLincoln SquareSeptember 30 - October 1
Taste Talks All-Star BBQPalmer SquareSeptember 29 - October 1