Update: Due to COVID-19, most of these events have been cancelled.
Spring is in the air so get your calendars out and start making plans for Summer, 2020!
MAY 2020
- Chicago Kids and Kites Fest, Saturday, May 2, 2020, Free Admission, 10am–4pm, Cricket Hill in Lincoln Park, W. Montrose Drive
- Chicago Beer Fest, Saturday, May 2, Soldier Field
- James Beard Foundation Awards May 4, Lyric Opera
- Illinois Craft Beer Week (ICBW), May 10-17, throughout Chicago and Illinois
- Lincoln Park Wine Fest (6th annual) Friday-Sunday, May 15-17, Jonquil Park, 1001 W. Wrightwood
- Manifest Urban Arts Festival, May 15 Wabash Arts Corridor between Michigan and Clark and Congress and Roosevelt
- Bark in the Park, May 16, Soldier Field
- 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
- Belmont-Sheffield Music Fest, May 23, 24, on Sheffield from Belmont to Roscoe
- 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

JUNE 2020
- Chicago Blues Festival, June 5–7, Millennium Park
- Lincoln Park Greek Fest, June 5 – 7, 2020, Sheffield Avenue outside St. George Greek Orthodox Church. Free.
- Harvard Milk Days, June 5 – 7, Harvard, IL.
- 57th Street Art Fair June, 6 and 7, Hyde Park
- Printers Row Lit Fest June 6 & 7, South Loop along Dearborn
- Wingout Chicago, June 6 and 7, 2 to 6 pm. St. Michael’s parking lot in Old Town
Hyde Park Brewfest. June 6 – 7 , downtown Hyde Park, 53rd and Harper Court West Loop Fizz Fest, Saturday-Sunday, June 6-7, 1000 W. Washington Blvd. (at Morgan), Chicago - Run for the Zoo 10K, 5K, and kids’ stampede, June 7, Lincoln Park Zoo and Lincoln Park
- Chicago Underground Film Festival June 10-14, 2558 W 16th Street, Stage 18
Spring Awakening 2020, June 12-14, Union Park, 1501 W. Randolph - Naked Bike Ride, June 13, departing from Fulton River Park
- Andersonville Midsommarfest, Friday, June 12-Sunday, June 14, 5200 N. Clark ok
- Ribfest Chicago June 12-14, Lincoln / Irving Park / Damen
- Old Town Art Fair June 13 – 14, Old Town Triangle Historic District
- Wells Street Art Festival June 13-14, Old Town, on Wells between North and Division
- Winnetka Music Festival (4th annual), Friday-Saturday, June 19-20, Elm Street and Lincoln Ave., Winnetka
- Festa!Pasta!Vino! Italian Street Festival, June 19 – 21, 2020, 24th & South Oakley
- Country LakeShake 2020, Fri, Jun 19 – Sun, Jun 21, Huntington Bank Pavilion at Northerly Island, 1300 S Linn White Dr
- Craft Brews At Lincoln Park Zoo June 19 & 20, Lincoln Park Zoo
- 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 Summerfest June 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.
- Father’s Day BBQ, June 21, with a cash bar, Brookfield Zoo.
- Swedish Days, June 23 – 28, 2020, Downtown Geneva
- Millennium Art Festival June 26, 27, 28 2020, downtown Chicago at Lake Street and Michigan
- Logan Square Arts Festival, June 26, 27 & 28, Milwaukee, Logan & Kedzie
Pride In The Park June 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 ParkHyde Park Brew Fest, June 2020 dates not confirmedGreen Music Fest, Wicker Park, June date, TBA
JULY 2020
- Windy City Ribfest in Uptown (12th annual), Friday-Sunday, July 3-5, Lawrence & Broadway (Uptown),
- Chicago Eyes to the Skies Festival, Friday-Sunday, July 3-5, Lisle Community Park, 1825 Short St., Lisle, IL
- The African/Caribbean International Festival of Life, July 3-5, Washington Park, 55th & Cottage Grove
- Fourth of July Fireworks, July 4, dusk, Navy Pier, 600 E. Grand
- Lake Forest Festival & Fireworks (14th annual), Saturday, July 4, Deerpath Park, Deerpath and Hastings Rd., Lake Forest, IL
- Chosen Few DJs Music Fest & Picnic, Saturday, July 4, Jackson Park (South Lake Shore Drive near 63rd Street), Chicago
- Taste of Chicago 2020, Wed, July 8 – Sun, July 12, Grant Park, 337 E Randolph St ok
- Irish American Heritage Festival, July 10-12, 4626 N Knox Ave., Chicago,
- Windy City Smokeout, Fri, Jul 10 – Sun, July 12, United Center
- Square Roots Festival, July 10-12, Lincoln Square on Lincoln between Montrose and Wilson
- West Fest, July 10, 11 &12, Chicago Avenue between Damen Avenue and Wood Street (1800W – 2000W Chicago Ave.)
- Roscoe Village Burger Fest (14th annual), Saturday/Sunday, July 11-12, 2000 W. Belmont (at Damen), Chicago
- Bastille Day 5/8K Run & Walk, July 13, Cannon Drive & Fullerton
- Green City Market Chefs BBQ, July 16, Lincoln Park
- Pitchfork Music Festival 2020, July 17-July 19, Union Park, 1501 W Randolph St.
- BenFest 2020, July 17-19, St. Benedict’s, 2215 W. Irving Park Rd
- Race to Mackinac and Parade of Boats, July 18, from Navy PierSilver Room Block Party, July 18, Downtown Hyde Park,
- 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
- Jeff Fest, Friday-Sunday, July 31-August 2, Jefferson Memorial Park, 4822 N. Long (Lawrence and Milwaukee Avenues), Chicago
- EdgeFest, August 1,2, Broadway between Thorndale and Ardmore
- 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.
- Highwood Garlic Fest, Everts Park, August 12, northern suburb
- 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
Chicago Caribbean Carnival, Saturday August 15 from 10:00 am to 9:00 pm
Midway Plaisance by the University of Chicago. - Oak Park Micro Brew Review, August 15, 2020 3-7pm. Marion Street, Downtown Oak Park
- Chicago Air & Water Show, August 15 & 16, 2020, North Avenue Beach
- 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
- TransAmerica Chicago Triathlon, August 29-30, 2020, Lake and surrounding areas
Chicago Jazz Festival, August 29–September 6, 2020, Chicago Cultural Center, Millennium Park and Venues Across Chicago - 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
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African Festival of the Arts, September (Labor Day) dates TBA, Washington Park
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Great American Lobster Fest, August 30-31 and September 1, Navy Pier
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Chicago Jazz Festival, August 29–September 6, 2020, Chicago Cultural Center, Millennium Park and Venues Across Chicago
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Taste of Polonia, September 4-7, 2020, Copernicus Center, 5216 W Lawrence Ave, Chicago
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North Coast Music Festival, September 4-6, Northerly Island
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¡Súbelo! – A Celebration of Pan Latin Music and Culture Sept. 11 – 12, 2020, Millennium Park
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Riot Fest, Sept. 11-13, Douglas Park Cultural and Community Center
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Chicago Bourbon & Barbecue Fest, Saturday/Sunday, September 12-13, 2000 W. Roscoe (at Damen), Chicago
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Jerk, Seafood & Vegan Festival, Sat Sept 12 -Sun Sept 13th, 3117 S. Cottage Grove/ S. Rhodes in Lake Meadows.
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Sam Adams\’ Lakeview Taco Fest (8th annual), Saturday/Sunday, September 19-20, Southport and Addison, Chicago
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Chicago Gourmet, September 25-27, Millennium Park
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Oktoberfest Chicago at St. Alphonsus, Friday-Sunday, September 25-27, St. Alphonsus Church, Southport & Lincoln, Chicago
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Randolph Street Market Festival, September 12-13, 1340 W. Washington St.