It’s time to think summer, Chicago. Show Me Chicago’s annual calendar of Chicago’s biggest and best festivals and events for the summer of 2020 is up and running. Make sure to put your favorites on your calendar and check back for more as the calendar will be updated throughout the season as more events are added and dates announced. AND let us know if we’ve missed anything.
ON-GOING SUMMER
Grant Park Music Fest 2020, June 10 through August 15, Most concerts take place on Wednesday and Friday evenings at 6:30 p.m., and Saturday evenings at 7:30 p.m. (Note: there will be no concert on Friday, July 3.), Millennium Park.
Navy Pier Summer Fireworks, Memorial Day through Labor Day, Wednesdays and Saturdays from Saturday, May 30 through Saturday, September ?: Wednesdays at 9:30 pm. & Saturdays at 10:15 pm.
Wright Plus House Walk, Saturday, May 16, Oak Park and River Forest
Chicago House Music Conference & Festival, May 21-23, Chicago Cultural Center & Millennium Park
Mole De Mayo, May 22-24, Ashland and 18th Street, Pilsen Navy Pier Fireworks, blast off May 23 (Wednesdays and Saturdays and July 4 through September 5)
Chicago Memorial Day Parade, May 23, wreath laying 11am, Parade noon, State St. from Wacker to Van Buren
Randolph Street Market Festival, May 23 – 24, 2020, first outdoor festival of the season, 1350 block W. Randolph and 1340 W. Washington Street between Ada and Ogden
Gospel Music Festival, May 26-May 30, Millennium Park & Citywide Locations
Bike the Drive, Sunday, May 24, Lake Shore Dr, post ride festival, Grant Park
Do Division Street, May 29th-May, 31st on Division Street between Damen and Leavitt (2000W-2200W Division St.)
Mayfest, May 29-31, Armitage at Sheffield LaGrange Pet Parade, May 30, 2020, line-up, 8:30 am., Downtown LaGrange, Cossitt Ave. & LaGrange Rd. Chicago Taco & Tequila Fest, May 30 & 31, 2500 N. Cannon Dr. Lincoln Park, Cannon Drive just north of Fullerton
Craft Beer Festival, Saturday, June 20, Morton Arboretum, Lisle
Taste of Randolph Street, June 19-21, offers three stages of music, 14 restaurant booths, and artisan vendors at Randolph Street & Peoria Street. Donation
Puerto Rican Parade, June 20, Division Street from Western Avenue to Sacramento Avenue, Humboldt Park
Chicago Vegandale, Vegan Food Festival, June 20, Butler Field in Grant Park. Free admission for children age 12 and younger
Chicago Food Truck Festival, June 20 & 21, South Loop Green Space
Ravenswood on Tap, June 20, 21, beer & spirits from local producers, food from nearby restaurants, live local music, and more Ravenswood Avenue and Berteau Avenue. Donation.
Chicago Pride Fest®, June 20-21, Halsted and Addison in Boystown Fountain Square Artisan SummerfestJune 20 & 21 2020, Evanston, IL- Sherman and Church Street
Make Music Day, June 21, various locations including Millennium Park and Navy Pier. Free.
Dragon Boat Races, June 21, teams compete in colorful boats on the river, music, dance, vendors, Ping Tom Memorial Park, 300 W 19th Street. Free.
Logan Square Arts Festival, June 26, 27 & 28, Milwaukee, Logan & Kedzie Pride In The ParkJune 27 & 28 2020, Grant Park
Highland Park Festival of Fine Arts, June 27 & 28, Downtown Highland Park Art Center
Renegade Craft Fair, June 27, 28 food trucks and craft cocktails for sale, Andersonville, Clark Street (from Edgewater Ave. to Bryn Mawr Ave.). Free
Chicago Pride Parade steps off at noon on Sunday, June 28, 2020, at Montrose Avenue and Broadway in Uptown and ends near the intersection of Diversey Parkway and Sheridan Road in Lincoln Park Hyde Park Brew Fest, June 2020 dates not confirmed Green Music Fest, Wicker Park, June date, TBA
Chinatown Summer Fair, Saturday/Sunday, July 18-19, Wentworth Avenue & Cermak Rd. (aka 22nd Street), Chicago
Chicago Food Truck Festival at Wrigley Field, July 25, 2020
Chicago Margarita Festival, July 25 – July 26, Navy Pier, 600 E Grand Ave
Taste of Lincoln Avenue (37th annual), Saturday/Sunday, July 25-26, North Lincoln Avenue between Fullerton & Wrightwood, Chicago
Randolph Street Market Festival, July 25, 26 2020, outdoor festival vintage, antiques, entertainment, food, drinks 1350 block W. Randolph and 1340 W. Washington Street between Ada and Ogden
Lollapalooza Music Festival 2020, Thu, Jul 30 – Sun, Aug 2, Grant Park, 337 E Randolph St OK
Jeff Fest, Friday-Sunday, July 31-August 2, Jefferson Memorial Park,4822 N. Long (Lawrence and Milwaukee Avenues), Chicago
Wicker Park Fest, July dates TBA, on On Milwaukee Ave., from North Ave. to Ashland Ave.
AUGUST 2020
Lollapalooza. Photo: Chicago Tribune
Jeff Fest, Friday-Sunday, July 31-August 2, Jefferson Memorial Park,4822 N. Long (Lawrence and Milwaukee Avenues), Chicago
EdgeFest, August 1,2, 5600 N. Ashland
Lollapalooza Music Festival 2020, July 30 – August 2, Grant Park, 337 E Randolph St
Ginza Festival, August 7, 8, & 9 2020, Midwest Buddhist Temple
Festival Cubano, August 7-9, Riis Park, Fullerton and Narragansett
Retro on Roscoe, August 7-9th, 2020, Roscoe Village on Roscoe
Bud Biliken Parade, second Saturday in August, King Drive through the Bronzeville and Washington Park neighborhoods on the city’s south side
North Halsted Market Days, August 8-9, 2020, from Belmont to Addison on North Halsted St.
Edison Park Fest 2020, August 14-16, Sidewalks along Northwest Highway in Edison Park neighborhood
.Glenwood Avenue Arts Fest, August 14-16, 2020, Rogers Park, Glenwood Avenue Arts District
Sangria Festival, August 15 & 16, 2020, Humboldt Park lawn
Naper Pride Fest (NEW Event), Friday-Saturday, August 21-22, Naperville, IL (Music concert at North Central College on Friday; fest on grounds of Naper Settlement on Saturday)
Ukrainian Days Festival, August 22-23 2020 Smith Park (Grand/Campbell)
Taste of Greektown, Friday-Sunday, August 21-23, 300 S. Halsted, Chicago
Logan Square Social, Saturday, Aug 29–Sun, Aug 30, Humboldt Blvd. & Armitage
Great American Lobster Fest, August 30-31 and September 1, Navy Pier
Chicago Hot Dog Fest, August dates TBA, Chicago History Museum
Clark After Dark, August dates, TBA, River North, at 420 N. Clark St on W. Hubbard Street, between N. Clark and N. Lasalle.
SEPTEMBER 2020
Chicago Gourmet Photo: Carole Kuhrt-Brewer
African Festival of the Arts, September (Labor Day) dates TBA, Washington Park Great American Lobster Fest, August 30-31 and September 1, Navy Pier Chicago Jazz Festival, August 29–September 6, 2020, Chicago Cultural Center, Millennium Park and Venues Across Chicago Taste of Polonia, September 4-7, 2020, Copernicus Center, 5216 W Lawrence Ave, Chicago North Coast Music Festival, September 4-6, Northerly Island ¡Súbelo! – A Celebration of Pan Latin Music and Culture Sept. 11 – 12, 2020, Millennium Park Riot Fest, Sept. 11-13, Douglas Park Cultural and Community Center Chicago Bourbon & Barbecue Fest, Saturday/Sunday, September 12-13, 2000 W. Roscoe (at Damen), Chicago Sam Adams’ Lakeview Taco Fest (8th annual), Saturday/Sunday, September 19-20, Southport and Addison, Chicago Chicago Gourmet, September 25-27, Millennium Park Oktoberfest Chicago at St. Alphonsus, Friday-Sunday, September 25-27, St. Alphonsus Church, Southport & Lincoln, Chicago Randolph Street Market Festival, September 12-13, 1340 W. Washington St.
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