May 20 - 22, 2022: Chicago Mayfest

May 21, 2022: Chicago Spring Tequila Tasting Festival

May 27 - 29, 2022: Mole de Mayo Festival

June 2 – 5, 2022: Cream of Wheaton

June 2 – 5, 2022: Maifest Chicago

June 3 – 5, 2022: Lincoln Park Greek Fest

June 3 – 5, 2022: Do Division Street Fest

June 4, 2022: Chicago Gospel Music Festival

June 4, 2022: Jonquil Park Family Festival

June 4 – 5, 2022: Windy City Hot Dog Fest

June 4 – 5, 2022: 75th Annual 57th Street Art Fair

Sundays June 5 – Dec. 18, 2022: Maxwell Street Market

June 9 – 12: Chicago Blues Festival

June 10 – 12, 2022: Andersonville Midsommarfest

June 11, 2022: Vegandale Fest

June 11, 2022: Chi-Soul Fest

June 11 – 12, 2022: Old Town Art Fair

June 11 – 12, 2022: Hyde Park Summer Fest

June 11 – 12, 2022: Ravenswood On Tap

June 11 – 12, 2022: Wells Street Art Festival

June 11, 18 & 25, 2022: Taste Of Chicago 

June 15: Puerto Rican People’s Parade

Select Wednesday, Friday & Saturdays June 15 – Aug. 20: Grant Park Music Festival

Wednesdays June 15 – Oct. 12: Ravenswood Farmers Market

June 17 – 19, 2022: The Lyrical Lemonade Summer Smash

June 17 – 19, 2022: Taste of Randolph Street (Get VIP Tickets)

June 18 – 19, 2022: Chicago Pride Fest

June 18 – 19, 2022: Artists of the Wall Music & Arts Festival

June 18 – 19, 2022: Gold Coast Art Fair (Get VIP Tickets)

Select Mondays & Thursdays June 20 – Aug. 18: Millennium Park Summer Music Series

June 24 – 26, 2022: Chicago Michelada Festival

June 24 – 26, 2022: Logan Square Arts Festival

June 25, 2022: Célébrez en Rosé

June 25 – 26, 2022: Pride In The Park Chicago 

June 26, 2022: Chicago Pride Parade

July 2 – 4, 2022: African/Caribbean International Festival Of Life 

July 4, 2022: Fourth Of July Fireworks At Navy Pier

Select dates July 6 – September 17, 2022: Chicago Summerdance

July 8 – 10, 2022: West Fest 

July 8 – 10, 2022: Taste Of Chicago 

July 8 – 10, 2022: Square Roots Craft Brew & Music Festival 

July 8 – 10, 2022: Spring Awakening Music Festival

July 9 – 10, 2022: West Loop Summer Fest

July 9 – 10, 2022: Southport Art Fest

Select Tuesdays July 12 – Aug. 30: Millennium Park Summer Film Series

July 13, 2022: Bastille Day Chicago 

July 14 – 15, 2022: Fresh Fest

July 15, 2022: Horner Brew Fest

July 15 – 17, 2022: Millennium Art Festival

July 15 – 17, 2022: Roscoe Village Burger Fest 

July 15 – 17, 2022: Pitchfork Music Festival 

July 22, 2022: Chicago Yacht Club Race To Mackinac

July 22 – 24, 2022: Colombian Fest 

July 22 – 24, 2022: Wicker Park Fest 

July 23 – 24, 2022: Chicago Margarita Festival

July 23 – 24, 2022: Pizza City Fest

Sundays July 24 – Sept. 4, 2022: Sundays on State

July 28 – 31, 2022: Fiesta Del Sol 

July 28 – 31, 2022: Lollapalooza 

July 29 – 31, 2022: Jeff Fest

July 30 – 31, 2022: Randolph Street Market Festival

July 30 – 31, 2022: Chinatown Summer Fair 

Dates TBA, 2022: Taste Of River North

Aug. 4: Art Uncorked: An Afternoon of Art + Wine

Aug. 4 – 7, 2022: Windy City Smokeout 

Aug. 5 – 7, 2022: Dancing in the Streets

Aug. 5 – 7, 2022: Festa Italiana

Aug. 6 – 7, 2022: Northalsted Market Days 

Aug. 6 – 7, 2022: Latinxt Music Festival

Aug. 12 – 14, 2022: Edison Park Fest

Aug. 12 – 14, 2022: Retro on Roscoe 

Aug. 13 – 14, 2022: My House Music Festival 

Aug. 13 – 14, 2022: Thirsty Ears

Aug. 13 – 14, 2022: Chicago Fried Chicken Fest

Aug. 13 – 14, 2022: Printer’s Row Art Fest

Aug. 18, 2022: Clark After Dark

Aug. 19 – 21, 2022: Ribfest Chicago 

Aug. 19 – 21, 2022: Ruido Fest

Aug. 20, 2022: Chicago Caribbean Carnival

Aug. 20 – 21, 2022: Chicago Air & Water Show 

Aug. 20 – 21, 2022: Sangria Festival 

Aug. 26 – 28, 2022: Taste Of Greektown 

Aug. 27 – 28, 2022: Transamerica Chicago Triathlon 

Dates TBA, 2022: Ginza Festival Chicago 

Dates TBA, 2022: Great American Lobster Fest 

Dates TBA, 2022: Bud Billiken Parade