April
Sound of Silent Film Festival, 4/20, Davis Theater
Afro Fusion Easter Day Party, 4/21, The Promontory
CineYouth Festival, 4/26-28, Music Box Theatre
Windy City Horrorama, 4/26-28, Davis Theater
Chicago Wine Fest, 4/27, Lincoln Park Zoo
Randolph Street Market, 4/27-28, West Loop
May
Kids and Kites Festival, 5/4, various locations
MoonRunners Music Festival, 5/4-5, Reggies
James Beard Awards Gala, 5/6, Lyric Opera
Hyde Park Food Truck Fest, 5/11
Renegade Craft Fair, 5/11-12, Pilsen
Chicago Riverwalk Season Celebration, 5/13-19
Día del Niño, 5/18, Pilsen
Open Air Music Festival, 5/18-19, Seatgeek Stadium
Hyde Park Handmade, 5/19, The Promontory
Sweets and Snacks Expo, 5/21-23, McCormick Place
House Music Conference and Festival, 5/23-25, various locations
International Mr. Leather, 5/23-27, Congress Plaza Hotel
Mole de Mayo Festival, 5/24-26, Pilsen
Live on the Lake!, 5/24-9/1, Navy Pier
Belmont-Sheffield Music Festival, 5/25-26, Lakeview
Navy Pier Fireworks, 5/25-9/31, Navy Pier
Bike the Drive, 5/26, Lake Shore Drive
Maifest Chicago, 5/30-6/2, Lincoln Square
Chicago Gospel Music Festival, 5/31-6/1, Chicago Cultural Center and Millennium Park
Do Division Street Fest, 5/31-6/2, West Town
June
Gold Coast Art Fair, 6/1-2
Hyde Park Community Art Fair, 6/1-2
57th Art Street Fair, 6/1-2, Hyde Park
Millennium Park Summer Film Series, 6/5-8/14
Harper Court Music Series, 6/5, Hyde Park
Chicago Blues Festival, 6/7-9, Millennium Park
Spring Awakening, 6/7-9, Poplar Creek
Andersonville Midsommarfest, 6/7-9
Old Town Art Fair, 6/8-9
Wells Street Art Festival, 6/8-9, Old Town
Printers Row Lit Fest, 6/8-9
LatiNxt, 6/14-15, Navy Pier
Taste of Randolph, 6/14-16, West Loop
Chicago Taco & Tequila Fest, 6/15, Lincoln Park
Punk Black Chicago Fest Edition, 6/15-16, Beat Kitchen
Hyde Park Handmade, 6/16, The Promontory
Puerto Rican People’s Parade, 6/16, Humboldt Park
Pilsen Taco Fest 2019, 6/16-17
World’s Largest Block Party, 6/21-22, Greektown
Chi-Soul Fest, 6/21-22, Navy Pier
Gold Coast Greek Fest, 6/21-23, Annunciation Greek Orthodox Cathedral of Chicago
Ruido Fest, 6/21-23, Union Park
Country Lakeshake, 6/21-23, Huntington Bank Pavilion at Northerly Island
Chicago Food Truck Festival in the South Loop, 6/22-23
Chicago Pride Fest, 6/22-23 Lakeview
Ravenswood on Tap, 6/22-23
Mamby on the Beach, 6/23-24, Oakwood Beach
Chicago Summerdance, 6/27-8/24, various locations
Back Lot Bash, 6/28-30, Andersonville
Logan Square Arts Festival, 6/28-30
Dyke March, 6/29, Little Village
Navy Pier Pride, 6/29
Pride in the Park, 6/29, Grant Park
Beverly Art Walk, 6/29
Lyrical Lemonade Festival, 6/29-30, Douglas Park
Chi Town Hot Sauce Expo, 6/29-30, Seatgeek Stadium
TRQPiTECA Queer Pride Chicago, 6/30, Chinatown
Chicago Pride Parade, 6/30, Lakeview
July
Windy City Ribfest, 7/4-6, Uptown
Windy City Black Pride, 7/4-7, various locations
Harper Court Music Series, 7/5, Hyde Park
West Fest, 7/5-7, West Town
Chosen Few DJs Picnic & Festival, 7/6, Jackson Park
Chicago Michelada Fest 2019, 7/6-7, Pilsen
Taste of Chicago, 7/10-14, Grant Park
Square Roots Craft Brew & Music Festival, 7/12-14, Lincoln Square
Irish Festival, 7/12-14, Irving Park
Roscoe Village Burger Fest, 7/13-15
Chinatown Summer Fair, 7/15
Wicker Park Fest, 7/26-28
Pitchfork Music Festival, 7/19-21, Union Park
Silver Room Block Party, 7/20, Hyde Park
Water Lantern Festival, 7/20, Humboldt Park
Dearborn Garden Walk, 7/21, Old Town
Fiesta del Sol, 7/25-28, Pilsen
Wakandacon, 7/26-28, Hyatt Regency McCormick
Ghana Fest, 7/27, Washington Park
Chicago Margarita Festival, 7/27-28, Navy Pier
South Loop Beer and Cider Fest, 7/27
Bantu Fest, 7/27-28, Hyde Park
August
Harper Court Music Series, 8/1, Hyde Park
Lollapolooza, 8/1-4, Grant Park
Soulful Chicago Book Fair, 8/3, Woodlawn
Belize Day in the Park, 8/4, Burnham Park
Out of Space Festival, 8/8-11, Evanston
Chicago Hot Dog Fest, 8/9-11, Lincoln Park
Retro on Roscoe, 8/9-11, Roscoe Village
Bud Billiken Parade, 8/10, Bronzeville
My House Music Festival, 8/10-11, Pilsen
Chicago’s Little Italy Festa, 8/16
Edison Park Fest, 8/16-18
Windy City West Indian Carnival, 8/17, Harvey
Sangria Festival, 8/17-18, Humboldt Park
Chicago Air and Water Show, 8/17-18, North Avenue Beach
South Shore Summer Festival, 8/21
Taste of Greektown, 8/23-25
Chicago Jazz Festival, 8/23-9/1, Chicago Cultural Center and Millennium Park
Villapalooza, 8/24, Little Village
Out at Wrigley, 8/25
México en el Corazón, 8/30, Millennium Park
African Festival of the Arts, 8/30-9/2, Washington Park
North Coast Music Festival, 8/30-9/2, Northerly Island
Taste of Polonia Festival, 8/30-9/2, Jefferson Park
September
Chicago Lowrider Festival, 9/2, Pilsen
Throwback Music Festival, 9/6-8, Gladstone Park
Renegade Craft Fair, 9/7-8, Wicker Park
Ride for Life Chicago, 9/7-8, Chicago-Michigan
Jerk, Seafood, and Vegan Festival, 9/7-8, South Loop
Out in the Park, 9/8, Six Flags Great America
Riot Fest, 9/13-15, Douglas Park
World Music Festival, 9/13-29, various locations
Fulton Market Harvest Fest, 9/14-16
West Loop Art Fest, 9/16-17
Expo Chicago, 9/19-22,Navy Pier
Edgewater Arts Festival, 9/28-29
Hyde Park Jazz Festival, 9/28-29
Oktoberfest, 9/28-30, Lakeview v