Skip to main content

May 18 - 31, 2026

Page 1


FESTIVAL GUIDE 2026

MAY

May 22-24

Belmont-Sheffield Music Fest

3200 N. Sheffield Ave.

Fri 5-10 pm, Sat-Sun, 11 am-10 pm

Belmont-Sheffield Music Fest kicks off summer for the 41st year. Just steps from the Belmont L station, you’ll find tribute bands, delicious eats and drinks, artisans and ven dors, and community entertainment stage. Lineup includes Stache, Rod Tuffcurls and The Bench Press, Jagged Little Pill, Trippin Billies, That Petty Band, The Divas and Hello Weekend, Lady Loomis, Good Country, Nelson Street Revival, Rumor Hazit, Chasing Rumours, Mellencougar and more. $10 suggested admission. Benefits Lakeview East Chamber of Commerce. chicagoevents.com/event/belmont-sheffield-music-fest

May 23

Memorial Day in Chicago

May 23-24

DoDivisionStreetfest

11 am: Daley Plaza, 50 W. Washington, Wreath laying Noon: State St., Lake to VanBuren, Parade www.chicago.gov/city/en/depts/dca/supp_info/parades. html

May 23-24

Barrington Art Fest

S. Cook and E. Station Sts. downtown Barrington 10 am-5 pm

16th annual event features 125+ artists, live painting classes, face painting, bubbles, jugglers, caricatures. Kids Art Zone offers art fest bingo, spin art, sand sculpture, coloring, drawing & more. Free entry. amdurproductions.com/new-barrington-art-festival

May 23-24

Forever Mine Fest

Union Park, 1501 W. Randolph St. R&B and house music fall in love at new fest with Keyshia Cole, Kelly Rowland, Juvenile, Mario, Kaytranada – 30+ artists on 3 stages, with special weekend host DJ Pharris. $135+ at foreverminefest.com

El Festival Latino Sueños Chicago

Grant Park, Ida B. Wells & Columbus Drive

Stunning visuals, and nonstop energy: Latin dance and electronic rhythms, grassroots Latin culture and local talent. Headliners include J Balvin, Kali Uchis, Fuerza Regida, with special appearance by Los Tucanes de Tijuana; local food vendors, art and activities. 1-day $189+, 2-day $329+. suenosmusicfestival.com

May 23-24

Randolph Street Market

1341 W. Randolph St., 10 am-5 pm

200+ dealers of art, antiques, fashion, furnishings, global goods and eats, live music. Better Homes & Gardens called it one of “9 Flea Markets You Must Visit Before You Die.” Tickets $14+ randolphstreetmarket.com

May 24-Sept. 3

Rockin’ in the Park

- Concert Series

Parkway Bank Park, 5501 Park Place, Rosemont. Sunday May 24/7-10 pm every Thurs and select Fri Classic tribute bands: Anthem (Styx), Heartache Tonight (Eagles), Chicago Tribute Anthology, American English (Beatles), Departure (Journey), Karat Magic (Bruno Mars), No Quarter (Led Zeppelin), Rhythm of the Rocketman (Elton John), Rod Tuffcurls & The Bench Press and more. No outside food or coolers. FREE admission. Parking FREE with validation. Bring your own chair. rosemont.com/thepark

WOOGMS Parade

Wellington & Pine Grove, 11 am

Tradition of the Wellington Oakdale Old Glory Marching Society for 60+ years is, "everybody marches, nobody watches," on Memorial Day and Labor Day. Find them on Facebook.

May 29-31

Do Division Streetfest

Division St between Damen & Leavitt (2000-2200W)

Two live music stages curated by the Empty Bottle and Subterranean mean diverse and cutting edge music; neighborhood boutiques add runway fashion show; family fun with petting zoo, mega slide, rockin’ kids music. Proceeds benefit LaSalle II Magnet School, A.N. Pritzker School. $10 suggested donation. westtownchamber.org/do-division

May 29-31

Maifest Chicago

Lincoln & Western Aves.

Fri 5:30-10 pm, Sat 12-10 pm, Sun 1-10 pm

May 29-31

Windy City Hot Dog Fest

4000 N. Milwaukee Ave. Fri 4-10 pm, Sat-Sun Noon-10 pm

Does ketchup belong on a hot dog? Decide for yourself as you judge some of Chicago’s most iconic hot dog stands vying for the title of Chicago’s Best Frankfurter. Browse arts & crafts, enjoy local talent on community stage, turn the kids loose in family-friendly activity zone; parade your dog at 11:45 am Sunday. Lineup includes Kashmir, Hairbangers Ball, Journey 2 Jovi. Sponsored by Six Corners Chamber. chicagoevents.com/ event/windy-city-hot-dog-fest

May

30

BARK

Lincoln Park Grove 2, Stockton Dr. N of LaSalle, 8 am-noon

Chicago’s oldest dog-friendly, outdoor fundraiser aims to raise $150,000 to support Anti-Cruelty’s mission to build a healthy community where pets and people thrive together. The 2-mile walk is followed by a party in the park – with canines too! Tickets $10 at anticruelty.org/events/bark

Back in Lincoln Square, with food, music, dancing, German Gemütlichkeit featuring Paloma, The Phenix, Pieptone!, Die Musikmeisters, Polkaholics and more. maifestchicago.com

May 30-31

Magnificent Mile Art Festival

875 N. Michigan Ave., 10 am-5 pm

Jewelry, fashion, glass and functional art, painting and photography by 60 juried artists from around U.S. on the sidewalks surrounding the former John Hancock Building. amdurproductions.com/magnificent-mile-art-festival/

May 31

Lakeview Porchfest 1-5 pm

Stroll the neighborhood and catch concerts by local talent on front porches. Tickets $11+ on Eventbrite.

MaifestChicago
KRAB

JUNE

June 1-7

Physical Theater Festival

Theater Wit, 1229 W. Belmont Ave. & The Dance Center at Columbia College, 1306 S. Michigan Ave. Theater that moves you, across cultures: from Argentina/France, Peru, S. Korea and the United States; a Scratch Night of works-in-progress; a Made in Chicago series. Partners include Chicago Department of Cultural Affairs and Special Events, Illinois Arts Council, Columbia College, cultural centers , and consulates. $18.75+ physicalfestival.com

June 3-August 26

Highwood Evening Gourmet Market

Everts Park, 111 North Ave., Highwood, Wednesdays 4:30-9 pm

Spread a picnic blanket Ravinia-style for Wednesday evening concerts (rock, Motown, British Invasion, Sinatra and more) artisan wares, and gourmet market with 60 vendors. Other special events include “Kick off to Summer” carnival June 5-7, Pride in the Park June 17, “Inferno Fest” of spicy foods June 24, Margarita Night July 29, Highwood Days Carnival and Taste of Highwood July 17-19, Garlic Fest August 12, Bloody Mary Fest Sun August 16 and “Nashwood”: Highwood meets Nashville, on Sept 4-6. celebratehighwood.org

June 4-7

Chicago Blues Festival

Thursday at Ramova Theatre, 3520 S. Halsted St. RSVP Fireside Chat on Mississippi Blues, John Primer Tribute to Theresa’s Lounge and Willie Clayton. Fri-Sun at Millennium Park, Michigan at Washington

Jay Pritzker Pavilion includes 55 Years of Alligator Records featuring Lil' Ed & The Blues Imperials, Ronnie Baker Brooks, Toronzo Cannon, Nick Moss, and Tinsley Ellis; 75 Years of Billy Branch with Kenny Neal and Ronnie Baker Brooks; Taj Majal and the Phantom Blues Band; Women in the Blues. Next Generation Blues tent showcases high schools, FREE. www.chicago. gov/city/en/depts/dca/supp_info/chicago_blues_festival.html

June 5 & September 4

First Friday Music Series

Sheridan Road, Devon-Pratt, 6-8 pm

Rogers Park Business Alliance and Loyola University Chicago host School of Rock, Angry Ankles, Fumee, Brad Meese, Red Line Rustlers, Sarah Coco, Collapsible Pony (F.K.A Lady K & The Back Beats), Val Leaventhal, The Snobs, and Andy Mitchell on business patios, with giveaways at Sister Jean Plaza, 6536 N. Sheridan Road. rpba.org

June 5-7

Lincoln Park Greek Fest

St. George Greek Orthodox Church, 2701 N. Sheffield Ave. Fri 5-11 pm, Sat 12-11 pm, Sun 12-10 pm Authentic Greek souvlaki (pork shish kebabs), pastitsio (Greek-style lasagna), chicken, veggies, spinach pie, gyros, and baklava. Enjoy Ormi Orchestra for modern and traditional music; Probable Cause and 16 Candles bands Friday night. $10 suggested donation. www.lincolnparkgreekfest.com

June 5-7

Ribfest Chicago

Lincoln, Irving-Berteau

Fri 4-10 pm, Sat-Sun 12-10 pm

Chicagoland restaurant BBQ masters compete for the title of “Best Ribs” and “People’s Choice” in time to music from top local and national acts. Kids Zone allows them to jump, ride, dance and climb. A fundraiser by Northcenter Chamber of Commerce, fest’s requested $10 donation benefits local schools, nonprofits, econ development and greening efforts. ribfest-chicago.com

June 6-7

American Writers Festival

Sat at American Writers Museum, 180 N. Michigan Ave.

Sun at Harold Washington Library Center, 400 S. State St.

Live Readings of memoirs, poetry [Gwendolyn] BrooksDay 2026, America at 250, Hip-hop journalism, thrillers, comedy, Black Chicago, Latino Chicago and more. FREE. americanwritersmuseum.org/ american-writers-festival/

June 6-7

Deerfield Art Festival

812 Park Ave., Deerfield Sat-Sun 10 am-5 pm

Live painting class and art demos amid 100 artists, Kids’ Art Zone. amdurproductions.com/deerfield-artfestival

June 6-7

57th Street Art Fair

57th Street, Kenwood-Wood lawn/Kimbark, 56th-57th Street, Sat 11-6 pm, Sun 10-5 pm

79th annual event is THE place to buy art, for seasoned collectors or those new to the art scene. Juried art fair features diverse media, with kids’ activities and live blues music. FREE admission. 57thstreetartfair.org

June 10-August 15

Grant Park Music Festival

Jay Pritzker Pavilion, Various days FREE seating on the Great Lawn and back half of the bowl; reserved seats $104+ for 4-6 concerts. Highlights include Leonard Bernstein’s “West Side Story,” Brahms Symphony No. 4, Haydn Military Symphony, Copland Symphony No. 3, American Choral Classics with the Grant Park Chorus, “Broadway Sings America” and the Independence Day Salute. grantparkmusicfestival.com

June 11-14

Fiestas Patronales Puertorriquenas

2800 W. Division

Celebrate Puerto Rican Day with authentic food, pastry, art and artisans. puertoricanfest.com

June 11-August 13 (exc July 2)

Lincoln Square Summer Concert Series

Giddings Plaza, 4731 N. Lincoln Ave. Thurs 6-8:30 pm

Listen to local musicians: The Sting Rays (’50s, ’60s and ’70s rock n roll); Los Perros Cubanos (Latin rock); Would You Kindly (female-fronted alt rock), Diamondback (country), Skip Class and The Dropouts (genrebending covers) and more, weather permitting. Beer and wine for sale. FREE. lincolnsquare.org/summerconcert-series

June 12-13

Scottish Festival & Highland Games

DuPage County Fairgrounds, 2015 Manchester Road, Wheaton Fri 9 am-8 pm, Sat 9 am-10 pm

Family-friendly outdoor event is a chance to explore Scottish culture without buying a plane ticket, from the Caber Toss to Highland Dancing to whisky seminars, marketplace and British car show. Proceeds benefit Chicago Scots (The Illinois Saint Andrew Society, the oldest-not-forprofit in Illinois) and Caledonia Senior Living & Memory Care. Parking free at fairgrounds. Admission: $23.75+ at Eventbrite, kids under 12 free. chicagoscots.org/festival

June 12-14

Andersonville Midsommarfest

June 12-14

Lyrical Lemonade Summer Smash Fest

Seatgeek Stadium, 7000 S. Harlem, Bridgeview

On Clark, Foster to Gregory Now in its 60th year, annual celebration of Swedish tradition in Chicago also highlights up-and-coming LGBTQIA+ artists; 50 music and entertainment acts on four stages, varied food and artisans. Lineup includes American English, Too Much Molly, Ariana DJ, Dancing Queen (ABBA Salute), Drag Queen Story Time, Lakeside Pride Latin Band, Chicago Gay Men’s Chorus and more. Admission is $16.50/day; $36.73 3-day. Proceeds to the Andersonville Chamber of Commerce, a 501c6 non-profit organization, to support festival expenses, neighborhood events, small business networking events, neighborhood beautification -- and over a dozen local non-profits. andersonville.org/midsommarfest

June 12-14

Lincoln Square Greek Fest

St. Demetrios Church, 2727 W. Winona

Authentic Greek food & pastries, Greek spirits & dancing, grand raffle. stdemetrioschicago.org/lincolnsquare-greekfest/

Premier hip-hop festival in the Midwest, with 50+ performers on three stages. Headliners include Lil Uzi Vert, Chief Keef, Skrillex, Yung Lean x Bladee, Playboi Carti and Lil Baby. 1-day $175+, 3-day $399+, VIP $265/$655, Diamond VIP 3-day $1,575. thesummersmash.com

June 13

Summer Solstice Uprising

Ridge Park, 9625 S. Longwood Drive

11 am-5 pm

13th annual art fair is a collaboration between the Chicago Park District, Ridge Park Advisory Council, the Beverly Area Arts Alliance and John H. Vanderpoel Art Association. beverlyarts.org

June 13-14

Arts on Sheridan

484 Central Ave., Highland Park 10 am-5 pm

100 curated artists across all media, kids zone, live music, food & drink, art demos. amdurproductions.com/artson-sheridan

June 13-14

Art in the Village

Hubbard Woods Park, 939 Green Bay Rd, Winnetka, 10 am-5 pm

Annual juried fine art fair sponsored by the 101-year-old North Shore Art League (NSAL) draws participants from across U.S. You’ll find oil painting, sculpture, mixed media, photography, and more.

northshoreartleague.org

diMellivnosrednA frammos

June 13-14

Old Town Art Fair 1763 N. North Park Ave. Sat 10-7pm, Sun 10-6pm 200+ juried fine artists: mixed media drawings, paintings, photography, ceramics, glass, fiber, jewelry, wood, metal, stone; 65+ gardens; children’s corner; food court; live music. $13 donation to benefit Old Town Triangle Association, Menomonee Club, local schools, arts, cultural and children’s programs, historic and architectural preservation. oldtownartfair.org

masterworks: this year, “Adriana Lecouvreur” and “LaBoheme.” operafestivalchicago.org

June 15-Aug 6

Millennium Park Summer Music Series

Jay Pritzker Pavilion, M & Th, 6:30 pm. Arrested Development, Sheila E and more. https://www.chicago. gov/city/en/depts/dca/supp_info/ millennium_park_music_series.html

June 19-20

Taste of Highland Park

Port Clinton Square, 600 Central Ave., Highland Park, Fri 5-10 pm, Sat 3-10 pm

Downtown Highland Park’s premiere dining and music festival. enjoyhighlandpark.com

June 19-20

Winnetka Music Festival

Entrances at Lincoln/Pine & Green Bay Road/Elm Street, downtown Winnetka

Emerging artists from the North Shore and beyond on 4 stages; wide variety of food, including vegan and gluten-free. Headliners include Trombone Shorty & Orleans Avenue and Father John Misty. Admission

$94.03-$224.65

June 13-14

Wells Street Art Festival

On Wells Street, Division to North Avenue

Sat 10 am-10 pm, Sun 10 am-8 pm 51th annual event draws 127 juried artists from across North America with traditional painting and sculpture, woodworking and metalsmithing, jewel craft, digital arts, and more; food from Old Town restaurants. Lineup includes 16 Candles, Rod Tuffcurls Presents Tuff Taylor: All Taylor Tribute, 3 Martini Jeannie, Band Calderisi, RAVIV Electric Cellos, Jesse White Tumblers, and more. www.wellsstreetartfest.us

June 13-July 5

Opera Festival of Chicago

North Shore Center for Performing Arts, 9501 Skokie Blvd., Skokie 6th annual fest dedicated to fully staged productions of Italian opera

winnetkamusicfestival.com

June 19-21

Taste of Randolph Street

On Randolph – Peoria to Racine Fri 5-10 pm, Sat-Sun 12-10 pm

Celebrate with local restaurants and the nation’s hottest up-and-coming bands. tasteofrandolph.org

June 19-21

Fiesta Back of the Yards

On Ashland, 45th-47th

Fest with local merchants, Latin cuisine, artisans, carnival rides, and live entertainment raises funds for Back of the Yards’ Neighborhood Council’s essential programs: Senior Shuttle Bus Program, computer employment readiness, year-around youth employment programs, and the awardwinning Ballet Folklórico program. bync.org/events/about-fiesta

June 20

Dragon Boat Race for Literacy

Ping Tom Memorial Park, 300 W. 19th St., 8 am-5 pm

Chinese dragon boat races date back 2,000 years. Each of the 33 teams this year consists of 14-20 paddlers and a drummer. Hosted by the Chinatown Chamber of Commerce, which promotes Asian culture and neighborhood literacy programs, the family event includes music and cultural dance performances. FREE. ccc-foundation.org

June 20-21

Artists of the Wall Festival

Pratt Beach, Farwell & the Lake Live public mural painting of 160 spaces on concrete bench-wall started 33 years ago as a way to prevent gang graffiti, respect Father’s Day, and bring Rogers Park together. This year’s theme is “We’re All Neighbors.” Images will remain until next May, when the wall is whitewashed in preparation for the 2027 Festival. www.loyolapark.org/aotw

June 20-21

Chicago Food Truck Festival

2300 S. Indiana Ave., 10 am-7 pm chicagofoodtruckfestival.com

June 20-21

Chicago Pride Fest

Halsted, Addison to Grace Street

25th annual celebration of LGBTQ+ culture and community with live mu sic from local and national talent on 3 stages, Youth Pride Space for teens, best of Chicago drag performance, Proud Pet Parade with prizes, dance exhibitions, and 150+ food and merchandise vendors. Headliners include Durand Bernarr, Alex Chapman + Zoe Gitter present: Gag, G Flip and Willa Ford.

Organized by Northalsted Business Alliance, fest seeks a $20 suggested donation to help pay performers and festival workers, support local non profits & community improvements like the Chicago Pride Crosswalks: 14 rainbow-paved intersections, the longest installation of its kind in the world. pridefestchicago.com

June 20-21

Gold

Coast Art Fair

Butler Field, S. Lake Shore & E. Monroe, 10 am-5 pm

200+ artists offer original works in painting, sculpture, jewelry, ceramics, mixed media, and more at 68th annual event. Enjoy Paint and Sip classes, henna art, caricatures, personalized poems; Kids Art Zone. amdurproductions.com/gold-coast-art-fair

June 24

Flavors of Albany Park

5-8 pm

17th annual event features four routes with 60+ restaurants – from Persian kebabs, to authentic Salvadoran pupusas, to Southeast Asian comfort food – in one of city’s most diverse neighborhoods, with after-party. Advance tickets only ($30 seniors/ kids; $45 general) at www.northrivercommission.org/flavors

June 26-27

Chicago Taco & Tequila Fest

Wrightwood Park, 2555 N. Ashland Ave. Fri 5-10 pm, Sat 11 am-10 pm

Authentic street-taco flavors and tequila flights with lively music. Online $15 admission includes sample-size Margarita for age 21+; $20 tequila tasting add-on. chicagoevents.com/ event/chicago-taco-tequila-fest

June 26-28

Logan Square Arts Festival

Centennial Monument, 3150 W. Logan Blvd.

Collaboration with neighborhood restaurants, art organizations and music venues captures the essence of this community, with a diverse lineup of performances and locally crafted beer and cocktails. logansquareaf.com/fest

June 27

Berwyn Pride Walk

Start outside The James Joyce Irish Pub, 7138 Windsor Ave., Berwyn, at 12 pm., ending at 2 pm at East Ave. Berwyn’s Pride Walk is a celebration of Berwyn’s remarkable transformation into one of Chicago’s most culturally vibrant and diverse communities. berwyn.net/pride

June 27-28

Millennium Art Festival

180 N. Stetson, 10 am-5 pm

Just steps from Millennium Park, enjoy thousands of paintings, sculptures, photography, jewelry, and more from 110 original artists. Food trucks, live music, face painting, art demos and Kids Zone. Free entry. amdurproductions.com/new-millennium-art-festival

June 27-28

Back Lot Bash

Cheetah Gym, 5248 N. Clark St. 4-10:30 pm Showcase for female artists and community organizations during Pride Weekend. Age 21+ Tickets $19.46+ backlotbashchicago.com

June 28

Pride Parade

Sheridan & Broadway-staging; viewing begins at Grace & Halsted, Kick-off at 11 am

55th annual parade is one of the nation’s oldest and largest Pride celebrations. Grand Marshals are journalist and historian Tracy Baim; civil rights leader Mona Noriega; philanthropist and community advocate Evette Cardona; and the Alliance of Il linois Judges, the state’s LG BTQ+ judges’ association. Together, they represent decades of leadership, advocacy, and service to Chicago’s LGBTQ+ community and beyond. This year’s theme, “Free to Be Proud,” is “intentional and declarative: Pride has never just been about celebration –it is about visibility, dignity, resilience, and

the right to exist safely and authentically. It is a reminder that no one is truly free until everyone is free to be.” Info and volunteer signups at pridechicago.org. FREE.

June 28

Roscoe Village Porchfest

1-5 pm Stroll the neighborhood and catch concerts by local talent on front porches. Sponsored by Lakeview Roscoe Village Chamber of Commerce. Tickets $11.44 on Eventbrite.

June 28-August 16

Bells of Summer Concert Series

Rockefeller Chapel, 5850 S. Woodlawn Ave., Sundays at 5 pm

Spread a picnic and enjoy 60th season of carillon played by virtuosos. rockefeller.uchicago.edu/the-carillon/ the-bells-of-summer

June 30-Aug 18

Millennium Park Summer Film Series

Jay Pritzker Pavilion, Tues, 6:30 pm Pavilion or Great Lawn seating, with state-of-the-art, 40-foot screen.

Series includes “Hamilton” (2020, PG13, July 28); “When Harry Met Sally” (1989-R, July 14) in Tribute to Rob Reiner, “Sinners” (2025, R, August 18) and more, FREE. chicago.gov/city/ en/depts/dca/supp_info/millennium_ park_film_series.html

PrideParade

JULY

July 3-5

International Festival of Life Union Park, 1501 W. Randolph St. Noon-10 pm daily

33rd annual African/Caribbean International Festival of Life (IFOL), offers reggae, Caribbean, R&B, pop, gospel, blues, jazz, African, Latin and world music, food, arts, crafts and games for the family. Tickets $20.98+ internationalfestivaloflife.com

July 3

Fourth of July-Wilmette

Yankee Doodle Dash and Fireworks, Gillson Park; Star Spangled Splash Centennial Park; special USA250 decal. wilmettepark.org/independenceday-celebration

July 4

Fourth of July

Hyde Park: 4th on 53rd Parade with marching bands, floats, kids on decorated bikes, 11 am, FREE after-fest in Nichols Park 4thon53rdparade.com

Jay Pritzker Pavilion in Millennium Park: Sat. 7:30 pm concert, Grant Park Music Festival Independence Day Salute featuring Aaron Copland’s “Fanfare for the Common Man,” Robert Lowden’s “Armed Forces Salute,” John Philip Sousa’s “Stars and Stripes Forever,” and more. Free seating in back half of bowl. grantparkmusicfestival.com

Navy Pier: Fireworks @ 10 pm navypier.org

Evanston: morning games, kids fun run, tennis finals, 2 pm parade, 7:30 pm band concert, 9:30 pm lakefront fireworks. evanston4th.org

Skokie: Noon parade, 6:30 pm festival and fireworks at Niles West HS (Oakton west of the Edens) skokie4th.org

Winnetka: Firecracker 5K run, 10 am parade, events on the Green, 7 pm concert, 9:20 pm fireworks at Duke Child’s Field. www.winpark.org/

July 4-5

Lincolnshire

Art Festival

405 Village Green S, Lincolnshire 10 am-5 pm

80 juried artists from around the US; live music, festival food, and beers from Half Day Brewery. amdurproductions. com/new-lincolnshire-artfestival

July 5

July 8-August 12 Northcenter Summer Concert Series

Town Square, 4100 N. Damen Ave. Wednesdays 7-8:30 pm FREE northcenterchamber.com/ summer-concertseries

July 10-12 Square Roots Festival

Love in Action Festival

DuSable Museum, 740 E. 56th Pl. Pride South Side hosts village of boutique items and handmade goods, performers, food and beverage vendors, community organizations. pridesouthside.org

July 8-12

Taste

of Chicago

Grant Park

46th annual event features 45+ food vendors dishing out bites that represent the city’s history as a melting pot of cultures. FREE entry, with food individually purchased. www.chicago. gov/city/en/depts/dca/supp_info/ taste_of_chicago.html

July 8-12

Windy City Smokeout

Outside United Center, 1901 W. Madison St., Lot C Thurs-Fri 2-10, Sat-Sun 1-10 BBQ by 20+ of the nation’s best pitmasters and the best of country music. Headliners include Twenty Oak Revival, Hootie & The Blowfish, Lainey Wilson, Jordan Davis, Blake Shelton and special DJ set by ADHD. General admission 1-day $75+/VIP $225+, 4-day General $299 at windycitysmokeout.com

On Lincoln, Montrose-Wilson Fri 5-10, Sat Noon-10, Sun Noon-9. Beer & Music TBA. Savor the best of Lincoln Square with live music, neighborhood restaurants, retail vendors and craft beer – all to benefit Lincoln Square Ravenswood Chamber of Commerce and Old Town School of Folk Music. squareroots.org

July 11

Chosen Few DJs Old School Reunion

63rd @ Hayes Drive, Jackson Park 7 am-10 pm

Founded by Wayne Williams in 1977, the Chosen Few Disco Corp. is a group of popular DJs from Chicago’s South Side – Williams, Jesse Saunders, Tony Hatchett, Alan King and Andre Hatchett – part of the first wave who created Chicago House Music. They are joined by Terry Hunter, Mike Dunn and Kim Parham and special guest DJs/live performers DJ Jazzy Jeff, DJ Boolu Mas ter, DJ Slugo, Barbara Tucker, Curtis Mc Clain and Christine Wiltshire for this fest that attracts 40,000 people annually. chosenfewdjs. com

July 11-12

Hungarian Gulyas Festival

Norridge United Church of Christ, 8260 W. Foster Ave.

Delectable food, festive music, merchandise, and dance. Find classic bottomless gulyás pot, lángos (fried bread), mititei (uncased sausage), crepes, kürtőskalács (spit cake), and new vegetarian gulyás and gulyás with beans - a Hungarian chili that comes with beans, sour cream, and paprika. Daily tix $35, 2-day $50, Kids age 6-12 $5 at gulyasfestival.com

July 11-12

Southport Art Fest

3733 N. Southport Sat 10 am-7 pm, Sun 10 am-6 pm

Stunning artwork by 100 high-quality artists in one of Chicago’s favorite boutique districts. Kids Zone, face painting, personalized poems. amdurproductions.com/southport-artfest

July 12-19

Chicago Duo Piano Fest

Nichols Concert Hall, 1490 Chicago Ave., Evanston Works by Mozart, Dubussy, Brahms, and Charles Ives, plus a world premiere that requires two pianos and four hands; by students and faculty of Music Institute of Chicago; plus, the Estrella Piano Duo, with works by Gershwin, Rachmaninoff and Barber, among others. www.musicinst.org/ chicago-duo-piano-festival

July 15-19

July 17-18

Taste of River North

On Wells, Ontario to Superior Fri 5-10 pm, Sat 11 am-10 pm

Savor signature dishes from some of the city’s top restaurants located in this iconic neighborhood, live music, Kids Zone (Fri 5-8, Sat 11 am-7 pm). tasteofrivernorth.com

July 18-19

Glencoe Festival of Art

700 Vernon Ave., Glencoe Sat-Sun 10 am-5 pm

Thousands of paintings, sculptures, photography, jewelry, and more by 100 original artists. Live music and art demos, Kids Zone with bubbles, face painting and fun art projects. Free entry. amdurproductions.com/newglencoe-festival-of-art/

July 17-19

West Fest

Chicago Ave., Wood to Damen Fri 5-10pm, Sat & Sun Noon-10pm

Planned by the West Town Chamber of Commerce, and programmed by Empty Bottle, this fest emphasizes cutting edge live music, neighborhood retail and restaurants, local fine artists and makers, a Kid Fest and Pet Fest. $10 suggested donation benefits Talcott Fine Arts & Museum Academy and West Town Chamber. westtownchamber.org

July 18-19

Ravenswood on Tap

Ravenswood & Berteau Avenues Sat Noon-10 p.m., Sun Noon-8 p.m.

July 17-19

Colombian Fest Chicago

Humboldt Park, North & Albany

Annual event celebrates Colombian independence from Spain, declared on July 20, 200+ years ago. Entertainment includes Guayacan Orquesta, Jose Alberto, Checo Acosta, Yeison Landero and more. Tickets $50.10+ colombianfestchicago.com

July 17-19

Roscoe Village Burger Fest

2000 W. Belmont Ave. Fri 5-10 pm, Sat & Sun 11-10 pm

Hyper-local festival celebrates Malt Row. Music lineup includes She’s Crafty, Punk’d, Serengeti,The Microphone Misfitz with special guest stars: Toronzo Cannon & Joanna Connor; NO MEN, wht.rbbt.obj, Guardrail, CalicoLoco, Sweetie, Lydia Cash, Siderunners, Billy Joel Jr. and pop-up performances by The Rhinemaidens. CASH only/ATMs on-site. Suggested $10 donation benefits small business support and public art placemaking. ravenswoodchicago.org/signatureevents/ravenswood-on-tap

July 18-19

Renegade Craft Fair

Rotary Fest

164 Lions Drive, next to Elk Grove HS

Wed-Thur 6-10:30 pm, Fri 6-11, Sat 2-11, Sun 2-8 pm

Carnival all five days, live music, fireworks Fri after concert in fundraiser for local, national, international causes. elkgroverotaryfest. com

Choose Chicago’s best burger from top eateries, enjoy arts & crafts, kids’ zone, live music on two stages. $10 suggested donation benefits Lakeview Roscoe Village Chamber of Commerce. chicagoevents.com/event/ roscoe-village-burger-fest/

July 17-19

Tacos y Tamales Festival

Ashland & Blue Island

Fri 5-10 pm, Sat-Sun Noon-10 pm

Modeled after a traditional open-air market, Pilsen festival offers authentic food, street cantinas, live music and dance performances and a variety of vendors. A portion of $7 suggested admission benefits Pilsen Arts and Community House and Frida Community Organization for family support. chicagotacofest.com

Logan Square: N. Kedzie bet. Fullerton & Palmer Square, 11 am-6 pm 250+ curated artists: jewelry, fragrance, soap, fashion, ceramics and more. renegadecraft.com/event/ chicago-summer

July 18-19

Sheffield Garden Walk

Webster & Sheffield, Noon-5 pm 55th annual event features self-guided walking tour of 50+ gardens; live music; tours by Chicago Architecture Center; wine tastings; interactive installations and Family Fest with face painting, crafts and inflatables Saturday 10 am-1 pm at Oscar Mayer School, 2250 N. Clifton. Admission free, donations welcomed. Event programs $12 at St. Vincent de Paul Church. sheffieldneighborhood.org/ 2026-garden-walk

DearbornGardenWalk

July 19

Dearborn Garden Walk

Noon-5 pm

66th annual event sponsored by North Dearborn Association features private gardens and architectural tours, garden seminars and more.

dearborngardenwalk.com

July 23-26

Fiesta del Sol

Cermak & Loomis

Thu 3-10 pm, Fri-Sun 11 am-10 pm

Largest Latino fest in US draws half a million people with live entertainment, carnival, food, vendors. 54th year. FREE admission; megapass for unlimited carnival rides $65. fiestadelsol.org

July 23-26

Lincolnwood Fest

Proesel Park, 6915 N. Kostner Ave., Lincolnwood

Carnival rides, family fun tent (gymnastics, hula dancing and more), bingo, beer and wine garden, live bands including Journey2Jovi, Run Forrest Run, All American Throwback, 7th Heaven, iPop, 16 Candles and more. Lincolnwoodil.org/427/ Lincolnwood-Fest-2026

July 24-25

Chicago Gospel Music Festival

Jay Pritzker Pavilion, Millennium Park FREE. chicago.gov/city/en/depts/dca/supp_ info/chicago_gospel_musicfestival. html

July 24-26

Taste of Lincoln Avenue

2500 N. Lincoln, Fri 4-10 pm, Sat 12-10 pm, Sun 12-8 pm

Local food favorites; arts & crafts; whiskey and spirits tastings; dog parade, kids carnival, live music from Midwest bands. chicagoevents.com/event/taste-oflincoln-avenue

July 24-26

Wicker Park Fest

1400 N. Milwaukee Ave.

Indie music lineup of 50+ local and national acts, installations by local artists, Pet Fest, 200+ local businesses that live up to eclectic neighborhood’s reputation. $10 suggested donation because street festivals are nonprofit fundraisers, not city-funded events. wickerparkbucktown.com

July 25

Words of Wonder

Literary Festival

Dr. Conrad Worrill Track & Field Center, 10201 S. Cottage Grove Ave. 11 am-6 pm

5th annual event offers vibrant storytelling led by beloved Black authors and illustrators; story-inspired dance, live music, and drumming rooted in Indigenous and African traditions; hands-on writing workshops; diverse marketplace of book vendors and community organizations; tasty snacks, healthy food, fun giveaways. Free, but register at wowlitfest.com

July 25-26

Art at the Glen

Glen Town Center, 2030 Tower Drive, Glenview, 10 am-5 pm

130+ juried artists, from traditional to modern: paintings, sculpture, photographs, jewelry and more! Live music, art demos, kid-friendly art tent. Free entry, parking. amdurproductions. com/art-at-the-glen

July 25-26

Chinatown Summer Fair

Wentworth Ave. from Cermak Ave. to 24th, Sat 11 am-10 pm, Sun 10-7 pm

Celebration of Far East food, art and music opens with lion dance, then performances, kung fu demonstra-

tions, samplings from Chinatown restaurants & unique gift shops. Entertainment will include Too Much Molly Saturday. FREE admission. ccc-foundation.org/summer-fair/

July 26

St. Ita’s Taste of Summer

5500 N. Broadway, 9:30 am-5 pm

Parishioners serve up Vietnamese, Mexican, Nigerian, Filipino, Haitian, American food and more for sale. motherofgodchicago.org

July 29-August 2

Lake County Fair

1060 E. Peterson Rd, Grayslake Wed-Thu 12-10 pm, Fri 12-11 pm, Sat 10 am-11 pm, Sun 10 am-8 pm

Celebrating its 97th year, the Lake County Fair offers high-flying motocross earth-shattering monster trucks, demolition derby, pulse-pounding bull riding; canine stunts, pig races, queen pageants, talent contests and carnival. Examine exhibitors’ blue-ribbon work for quilts to cattle, pickles to petunias, and sheep to scrapbooks. Daily admission $5 seniors/kids age 6-12, $15 over age 13. lcfair.com

July 30-August 2

Lollapalooza Grant Park

“Lollapalooza” means “extraordinarily impressive,” which is fitting for a hiphop, alternative and techno fest with 170+ acts that attracts nearly half a million attendees annually, with food and drinks from Chicago’s favorite restaurants. Headliners include Lorde, John Summit, Tate McCrae, The XX, Charli XCX, The Smashing Pumpkins, Olivia Dean and Jennie. Limited 1-day passes at $185+; otherwise wait-list and sold out. lollapalooza.com

July 31-August 2

Chicago Italian Beef Fest

Jefferson Memorial Park, 4822 N. Long Ave. Fri 5-10 pm, Sat 12-10 pm, Sun 12-8 pm

“Same place, bigger flavor” as Jeff Fest, with two stages of live music and kids zone, sponsored by the Jefferson Park Chamber of Commerce. chica goevents.com/event/chicago-italianbeef-fest

AUGUST

August 1-2

Wilmette Art Fair

1141 Central Ave., Wilmette, 10 am-5 pm

100 original artists with paintings, sculptures, photographs, jewelry and more; face painting, live music. FREE entry, free parking in lot. amdurproductions.com/wilmette-art-fair

August 7-9

Ginza Holiday Festival

Midwest Buddhist Temple, 435 W. Menomonee St.

71th annual Japanese cultural festival featuring entertainment: Awa Odori and Minyo folk dancing, aikido martial arts and kendo swordsmanship, taiko drumming and more; Waza master artisans from Japan, whose handmade crafts have been passed down for over 300 years. Local artisans exhibit and sell artwork, jewelry, textiles from Japan, kimonos, and T-shirts. Food options include MBT’s famous Chicken Teriyaki; udon (Japanese cold noodles), grilled corn on the cob, kintoki (Japanese snow cone topped with sweet azuki beans); Japanese beer. ginzaholiday.com

August 7-9

Northalsted Market Days

Halsted Street, Belmont to Addison Fri 5-10 pm. Sat & Sun 11 am-10 pm

Half-mile long lineup of live music on 4 stages, 250+ vendors, arts, crafts, food and drink, dance demos, drag performances celebrates community; it’s one of Thrillist’s Can’t-Miss Queer Events, 2023 Best of Gay Cities Travel-Worthy Festival. $20 suggested donation helps support festival, local nonprofits, Pride Crosswalks. northalsted.com/main-events/ northalsted-market-days

August

8

Bud Billiken Parade

39th & MLK Drive to 51st/ Washington Park, 10 am-4 pm

Every summer since 1929, “The Bud” has united Chicago African Americans in music, dance, food, and laughter. It’s a space to praise their historic roots on the South Side. Founder Robert Sengstacke Abbott’s mission for the betterment of Chicago's youth sounds the clarion call for "Back to School," now for the 4th generation of Chicago Defender Charities, Inc. budbillikenparade.org

August 13-16

Taylor Street

Little

Italy Festival

Generations of Italians settled here from the late 1800s to the 1950s. Find fabulous food from award-winning area restaurants, continuous family entertainment, quality merchandise from Italy. oshows.com

August 14-16

Glenwood Avenue Arts Fest

6900 N. Glenwood Ave., Rogers Park Fri Cobblestone Jam 6-10 pm Sat 11 am-9 pm, Sun 11 am-7 pm

Organized by the community, immersive weekend event showcases 100+ artists, invites exploration of open studios, and pulsates with vibrant live entertainment across outdoor stages amid a delectable array of street food and craft beer offered by local merchants. It’s one of the few neighborhood festivals where attendees can directly engage with creators for unique handmade artworks. glenwoodave.org

August 15-16

Chicago Air and Water Show

Lakefront, Fullerton to Oak Street, 10:30 am-3 pm

Presented by the City of Chicago, with its epicenter at North Avenue Beach, the largest FREE show of its kind in the U.S. showcases military and civilian, historic and modern aircraft. Rehearsal Friday. chicago.gov/ city/en/depts/dca/supp_info/air_water_show.html

August 15-16

Printers Row Art Fest

728 S. Dearborn St., 10 am-5 pm 95 artists offer paintings, street art, jewelry, photography, sculpture, woodworking; personalized poems, live music. amdurproductions.com/ printers-row-art-fest-new

August 20-24

Living Newspaper Festival

Broadway Armory, 5917 N. Broadway Thurs-Sat, 7:30 pm, Sun 2 pm, Mon 7:30 pm

Inspired by the 1930s Living Newspapers of the Federal Theatre Project, this festival presents world premieres of 10-minute plays drawn from recent headlines. Tickets $15-$35. jackalopetheatre.org

August 21-23

Irish Fest

Chicago Gaelic Park, 6119 W. 147th St., Oak Forest Fri 4-11 pm, Sat 3-11 pm, Sun 1-8 pm Irish workshops, dancing and music; expanded Leprechaun Tent (children's entertainment); bagpipes. Lineup includes Socks in the Frying Pan, Billow Wood, Cailíní Lua, Derek Warfield & The Young Wolftones, Super Céilí, The Drowsy Lads, Kilmaine Saints, George Murphy & Friends, Waxie Dargles, Dennis Doyle, Jinty McGrath and The Larkin & Moran Brothers, One for the Ditch, Evin O’Riordan and more.

Admission: 1-day: $20.75, 2-day $37, 3-day $50; kids under 12: $7/$13/$19; reduced tix in advance online tickets.chicagogaelicpark. com

August 21-23

Lakeview Taco Fest

3500 N. Southport

Fri 4-10 pm, Sat 11 am-10 pm, Sun 11 am-9 pm

Judge Chicago’s best taco made with chicken, steak, chorizo, beef or other innovative filling. Pair it with exactly the right brew. Enjoy music on two stages and Mexican wrestling. chicagoevents.com/event/lakeviewtaco-fest

August 22

Oak Park Microbrew Review

Downtown Oak Park

Microbrew means micro-waste at the largest craft beer fest in Midwest. 19th anniversary event brings 40+ brewers of craft beers, ciders, seltzers, nonalcoholic options, live music and DJs and incredible food. sevengenerationsahead.org/event/opmbr

August 22-23

Evanston Art & Big Fork Festival

Church & Sherman

Sat 11 am-6 pm, Sun 10 am-5 pm

150 juried artists showing paintings, sculpture, jewelry, mixed media, photography and more near the “Big Fork,” an eclectic selection of food trucks, adult beverages and live music. Have a personalized poem written for you, or visit the Kids Art Zone for spin art, sculpture, coloring. amdurproductions.com/evanston-art-andbig-fork-festival

August 22-23

Thirsty Ears Festival

Wilson, Hermitage-Ravenswood Sat 2-11 pm, Sun 1-9 pm

Classical music street festival also offers beer and wine, vendors, kid-friendly activities and food trucks. acmusic.org/ events/thirsty-ears-program

August 27-30

Chicago House Music Festival & Conference

Chicago Cultural Center, 78 E. Washington St. & Millennium Park FREE www.chicago.gov/city/en/ depts/dca/provdrs/support.html

August 28-30

Edgewater Music Fest

Broadway & Thorndale

30+ bands on 2 stages, 100+ street vendors. edgewatermusicfest.org

August 28-30

Edison Park Fest

Northwest Highway/Oliphant Fri 5-10 pm, Sat 12-10 pm, Sun 12-9 pm

Food and music fest sponsored by the Edison Park Chamber of Commerce; proceeds benefit local beautification, civic and school fundraisers, Santa Express. $10 donation requested. edisonparkfest.org

August 28-30

Taste of Greektown

315 S. Halsted St. Fri 4-10 pm, Sat-Sun, 11 am-10 pm

35th annual event features Mediterranean flavors, from classic gyros and souvlaki to fresh seafood and decadent desserts; plus, the infectious sounds of Greek bands. chicagoevents.com/event/taste-of-greektown

August 28-30

Skokie Backlot Bash

Oakton, between Lincoln & Laramie Celebrate downtown Skokie’s legacy as an Essanay Studios film set with three days of live music on two stages; kids fun run, carnival rides, Rotary pancake breakfast, food & beer and more. Presented by Skokie Public Library, Village of Skokie, Skokie Park District. backlotbash.com

August 22

Chalk Howard Street Festival

Howard Street, Paulina-Ashland 11 am-7 pm

International 3D street artists and local 2D chalk artists will create vivid and interactive chalk drawings, with street squares available for public purchase. Live music and global cuisine. howardstreetchicago.com/ chalk-howard-street

August 29-30

Bucktown Arts Fest

Across from Holstein Park: 2200 N. Oakley Ave.

Begun in the 1980s when four artists wanted to display their work, this all-volunteer-run fest draws 40,000 people annually for art and live music that benefits arts education at Holstein Park and local classrooms. FREE. bucktownartsfest.com

August 29-30

Port Clinton Art Festival

600 Central Ave., Highland Park 10-5 pm

Historically ranked national festival draws 200 “best of the best” artists from around U.S., a collectors' favorite for 40+ years. Purple ribbon on select items indicates donation to WINGS, providing pathway to independence for domestic violence survivors. Find art demos and live painting classes, Kids Zone with art fest bingo, spin art, sand sculpture. Free entry. amdurproductions.com/ new-port-clinton-art-festival

weivekaL ocat
tseF

SEPTEMBER

September 3-6

Chicago Jazz Festival

Citywide, including Chicago Cultural Center & Millennium Park

Chicago Labor Day tradition for 40+ years, produced by Chicago Department of Cultural Affairs and Special Events (DCASE) and programmed with Jazz Institute of Chicago. FREE chicago.gov/city/en/depts/dca/supp_ info/chicago_jazz_festival.html

September 4-6

Taste of Melrose Park

Authentic foods, affordably priced; family entertainment and crafts. melrosepark.org/taste-of-melrose-park/

September 4-6

North Coast Music Festival

EDM to house and jam bands northcoastfestival.com

September 4-7

ARC Music Festival

House and techno music with 90+ artists. arcmusicfestival.com

September 4-7

Taste of Polonia

One of the nation’s largest festivals of Polish culture, Old World cuisine – and nonstop music. topchicago.org

-Compiled by Suzanne Hanney

Make sure to keep an eye out for our Fall Festival Guide in August!

StreetWise exists to elevate marginalized voices and provide opportunities for individuals to earn an income and gain employment. Anyone who wants to work has the opportunity to move themselves out of crisis. StreetWise provides “a hand up, not a handout.”

All vendors go through an orientation focusing on their rights and responsibilities as a StreetWise Magazine Vendor. Authorized vendors have badges with their name, picture and current year.

How StreetWise Works

Vendors purchase the magazine for $1.15 and sell it for $3 plus tips. The vendor keeps all of their earnings.

Buy the Magazine, Take the Magazine

When you buy the magazine, take the magazine, and read the magazine, you are supporting our microentrepreneurs earning an income with dignity.

New vendor orientation is every Tuesday and Thursday at 10 a.m. at 2009 S. State St. Find your nearest vendor at www.streetwise.org

Turn static files into dynamic content formats.

Create a flipbook
May 18 - 31, 2026 by StreetWise_CHI - Issuu