Chicago Festival Guide 2019

Ohhh summer.

Those 3 long blissful months that remind us Chicagoans why we put up with the even longer 9 of freezing temps, snow, and the occasional polar vortex. 

Oh yes, we LIVE for those beautiful hot summer days.

Filled with ice-cold cocktails on a favorite rooftop, brunching at any restaurant with an outdoor patio, lazy days at the beach, boat rides on Lake Michigan, late sunsets, bike riding the 606, beach volleyball, outdoor tennis, or really any outdoor recreational activity, and festivals. 

Ah yes, Chicago festivals. Every weekend from May to September is packed full with a wide range of fun for all. 

From free street fests to big ticketed events. From cultural to music to food.

If you like mixing and mingling amongst little white tents filled with bites, beers, and good ol’ fun, we’ve got you covered.

There are over 100 festivals coming to Chicago this summer and thanks to RedEye Chicago (which you grab at any newsstand for free) all festivals are listed out for YOU! 

Whether you’re a Chicago native or just visiting, you’re going to want to bookmark this page for the next time a Saturday (or Sunday) rolls around and you’ve got nothing to do. 🙂 


May

Maifest Chicago (Lincoln Square): May 30-June 2 : FREE

Pivot Arts Festival (Edgewater): May 31 – June 9 : $10-$15

Chicago Gospel Music Festival (Loop): May 31 – June 1 : FREE

Lincoln Park Green Fest: May 31 – June 2 : FREE

Taste of Mexico in Little Village: May 31-June 2 : FREE

Do Division Street Fest (West Town) May 31 – June 2 : $10 suggested donation


June

Chicago Ale Fest (Loop): June 1 : $49-$59

Gold Coast Art Fair (Loop): June 1-2 : $10

57th Street Art Fair (Hyde Park): June 1-2 : FREE

Wingout Chicago (Lincoln Park): June 1-2 : $56

Hyde Park Brew Fest: June 1-2 : FREE to attend, $30 to sample

Chicago Alternative Comics Expo (Boystown): June 1-2 : FREE

Chicago Underground Film Festival (Logan Square) : June 5-9 : $80-$90

Midsommarfest (Edgewater): June 7-9 : FREE

Chicago Blues Festival (Loop): June 7-9 : FREE

Ribfest Chicago (North Center): June 14-16 : $10 suggested donation

Spring Awakening Music Festival (Hoffman Estates): June 7-9 : $69+

Old Town Art Fair (Wells Street): June 8-9 : $10 suggested donation

Printers Row Lit Fest (Loop): June 8-9 : FREE

Pilsen Food Truck Social: June 8-9 : $5 suggested donation 

Puerto Rican People’s Parade (Humboldt Park): June 9 : FREE

Grant Park Music Festival (Loop): June 12-Aug 17 : FREE

Craft Brews at the Zoo (Lincoln Park Zoo): June 14-16 : $20-$79

Oakley Festa Pasta Vino (Lower West side): June 14-16 : $5-$7 suggested donation

Cinepocalypse (Loop): June 13-20 : $100-$175

Millennium Park Summer Music Series (Loop): June 13-Aug 15 : FREE

Pride Fest (Lakeview): June 22-23 : $10 suggested donation

Make Music Chicago (Various locations): June 21 : FREE

Country LakeShake (Northerly Island): June 21-23 : $80+

Logan Square Arts Festival: June 28-30 : $5 suggested donation

Back Lot Bash (Andersonville): June 28-30 : $35-100

Old St. Pat’s World’s Largest Block Party (West Town): $10

Ravenswood on Tap (North Center): June 22-25 : $5 suggested donation

Chicago Food Truck Festival (South Loop): June 23-23 : FREE

Chicago Mariachi Festival (Loop): June 30 : FREE

Pride Parade (Uptown-Boystown): June 30 : FREE

Chicago SummerDance (Various Locations): June 27-Aug 24 : FREE

Vegandale Food and Drink Fest (Loop): June 22 : $10

Millennium Art Festival (Loop): June 28-30 : FREE


July

International Festival of Life (Hyde Park): July 4-7 : $9.50+

Windy City Ribfest in Uptown: July4-6 : $5 suggested donation

West Fest (West Town): July 5-7 : $5 suggested donation

Taste of Chicago (Loop): July 10-14 : FREE, but must buy food tickets

Irish American Heritage Festival (Irving Park): Jule 12-14 : $10-$15

Square Roots Craft Brew & Music Fest (Lincoln Square): July 12-14 : $5-$20 suggested donation

Windy City Smokeout (Near West Side): July 12-14 : $40+

Roscoe Village Burger Fest: July 12-14 : $10 suggested donation

Southport Art Festival: July 13-14 : FREE

El Gran Fest Colombiano (Hermosa): July 19-20 : $25

Artfest Michigan Ave (Streeterville): July 19-20 : FREE

Taste of River North: July 19-21 : $5

Sheffield Music Festival & Garden Walk (Lincoln Park): July 19-21 : $10

Tacos y Tamales (Lower West Side): July 19-21 : $5 suggested donation

Chicago Craft Beer Festival (Lakeview): July 20-21 : $20-$50

Silver Room Block Party (Hyde Park): July 20 : $10 suggested donation

Ruido Fest (Near West Side): June 21-23 : $64+

Chinatown Summer Fair: July 21 : FREE

Rhythm World (Various Locations): July 22-28

Pitchfork Music Festival (Near West Side): July 19-21 : $75+

BenFest (North Center): July 19-21 : $5-$14

Fiesta del Sol (Lower West Sidde): July 25-28 : FREE

South Loop Beer & Cider Fest: July 27 : $15-$65

Taste of Lincoln Ave (Lincoln Park): July 27-28 : $10 suggested donation 

Margarita Festival (Near North Side): July 27-28 : $20-$65

Wicker Park Fest: July 26-28 : FREE

Andersonville Sidewalk Sale: July 26-27


August

Lollapalooza (Loop): Aug 1-4 : From $130

Black Harvest Film Festival (Loop): Aug 2-29

EdgeFest (Edgewater): Aug 3-4 : $5 suggested donation

Jeff Fest (Jefferson Park): Aug 3-5 : $5 suggested donation

Chicago Brewing District’s Dancing in the Streets (West Town): Aug 3-4 : $5 suggested donation

Chicago Hot Dog Fest (Lincoln Park): Aug 9-11 :$5 suggested donation

Ginza Holiday Festival (Lincoln Park) Aug 9-11 $5 suggested donation

Festival Cubano (Belmont Cragin): Aug 9-11 :$45+

Retro on Roscoe (North Center): Aug 9-11 : $10 suggested donation

Northhalsted Market Days (Lakeview): Aug 10-11 : $10 suggested donation

My House Music Festival (Pilsen): Aug 10-11 : donations accepted

Clark in the Dark (Near North Side): Aug 15 : $10

Glenwood Avenue Arts Fest (Rogers Park) Aug 16-18 : FREE

Edison Park Fest: Aug 16-18 : 45 suggested donation

Chicago Air & Water Show (Michigan Lakefront;Old Town Triangle): Aug 17-18 : FREE

Sangria Festival (West Town): Aug 17-18 : $15-$85

Pilsen Fest: Aug 17-18 : $5 donation 

Windy City West Indian Carnival (Hyde Park): Aug 17 : FREE

South Shore Summer Fest: Aug 21 : FREE

Women’s Funny Fest (Lakeview): Aug 23-26 : $15

Villapalooza (South Lawndale): Aug 24 : FREE

Ukranian Days (West Town): Aug 24-25 : $5 suggested donation 

Taste of Greektown: Aug 23-25 : $5 suggested donation

Bucktown Art Fest: Aug 24-25 : FREE

Chicago Jazz Festival (Loop): Aug 23-Sept 1 : FREE

The Great American Lobster Fest (Near North Side): Aug 30-Sept 1 : Free to attend, seafood package available

North Coast Music Festival (West Town): Aug 30-Sept 1

African Festival of the Arts (Washington Park): Aug 30-Sept 2

Taste of Polonia Festival (Jefferson Park): Aug 30-Sept 2


September-October

Throwback Music Festival (Norwood Park): Sept 6-8 : $5

Festival de la Villita (South Lawndale): Sept 6-8 : Free

German American Oktoberfest (Lincoln Square): Sept 6-8 : FREE

Ukranian Village Fest: Sept 7-8 : $5 suggested donation 

World Music Festival (Various locations): Sept 13-29 : FREE

Lakeview East Festival of the Arts: Sept 14-15 : $5 suggested donation 

Chicago Bourbon & Barbeque Fest (Roscoe Village): Sept 14-15

Riot Fest (Douglas Park): Sept 13-15 : $125+

Sam Adam’s Lakeview Taco Fest (Southport Ave Lakeview): Sept 21-22 : $10 suggested donation

Goose Island’s 312 Urban Black Party (Near West Side): Sept 20-21 : $10 suggested donation

Expo Chicago (Near North Side): Sept 19-22 : $20-$30

Bon Appetit’s Chicago Gourmet (Loop): Sept 27-29 $195+

Oktoberfest Chicago at St. Alphonsus (Lakeview): Sept 27-29 : $10

Edgewater Arts Festival: Sept 28-29 : $5 suggested donation 

West Town Food Truck Social & Art Walk: Sept 27-28 : FREE

Apple Fest (Lincoln Square): Oct 5-6

 

Happy festing, friends! 🙂

& thanks again to RedEye Chicago

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