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The Ultimate Chicago Summer Guide 2026: Festivals, Parades, Markets And More

Story Center by Story Center
June 14, 2026
Reading Time: 37 mins read
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CHICAGO — This city comes alive in the summer with parades, festivals, outdoor workouts, bar crawls and more.

There’s something to cover everyone’s interests, and events are held in every corner of the city. Whether you want to celebrate Pride Month, have a special night at Sox Park or work out in the heart of Downtown, we’ve got something for everyone in this guide of things to do this summer.

Here are more than 95 things to do in Chicago through September:

table visualization

Summer Fireworks

9 p.m. Wednesdays, 10 p.m. Saturdays May 23-Sept. 5

Navy Pier, 600 E. Grand Ave.

Bring a chair or blanket to the lawn of the Pritzker Pavilion to enjoy a free movie. Catch “When Harry Met Sally,” “Sinners” and more this summer.

ADVERTISEMENT

Free

Website

Millennium Park Workout Series

8-11:45 a.m. May 16-Sept.5 (no classes on July 4)

Grant Park, the Great Lawn, 201 E. Randolph St.

Head to free pilates, yoga, cardio kickboxing and Zumba in Millennium Park. Plus, some sessions have live music.

Free

Website

Chi Food Truck Fest

Fridays May 15-Oct. 2

Daley Plaza, 50 W. Washington St.

Food trucks will take to Daley Plaza every Friday offering a wide array of cuisines. Admission is free.

Free

Website

Millennium Park Summer Music Series

Mondays and Thursdays June 15-Aug. 6

Grant Park, Pritzker Pavilion, 201 E. Randolph St.

Enjoy free concerts in the parks on Mondays and Thursdays throughout the summer. Catch artists like Arrested Development, Radius, DJ Larz Natural and more.

Free

Website

Millennium Park Film Series

6:30 p.m. Tuesdays June 30-Aug.18

Grant Park, Pritzker Pavilion, 201 E. Randolph St.

Bring a chair or blanket to the lawn of the Pritzker Pavilion to enjoy a free movie. Catch “When Harry Met Sally,” “Sinners” and more this summer.

Free

Website

Vibes On Logan

Second Sunday of the month, May 17-Sept. 13

2600 W. Logan Blvd.

There will be a rotating lineup of DJs down Logan Boulevard throughout the summer, bringing the perfect rhythms for Chicago summer. Admission is free.

Free

Website

Harper Court Summer Music Series

Thursday June 4, July 9, Aug. 6, Sept. 10 6-9 p.m.

5235 S. Harper Court

Catch live music in Hyde Park all summer with a monthly concert series featuring artists like DJ Eric “ET” Taylor, Rich Medina, Shawnee Dez and more. Plus, steppers can compete in the annual Best Steppers Contest, which will have trophies and cash prizes for the winners. This event is free to attend.

Free

Website

Full Moon Jam

June 1-Sept. 27

Various locations, Lakefront trail

The Full Moon Jam is a concert series along the lakefront trail with live music from Evanston to Rainbow Beach throughout the whole summer.

Free

Website

Windy City Hot Dog Fest

May 29-31

4000 N. Milwaukee Ave.

The fifth annual Windy City Hot Dog Fest is returning to Portage Park as some of Chicago’s favorite hot dog stands compete for the title of “Best Frankfurter.” There will also be live music, a selection of arts and crafts vendors, plus a family zone with fun activities and a community stage that showcases local talent. Admission is free.

Free

Website

Do Divison Street Fest

May 29-31

Division Street between Damen and Leavitt streets

The weekend Divison street fest has food, drinks, shopping, a special fest just for kids and two live music stages programmed by the Empty Bottle and Subterranean. There is a $10 suggested donation upon entry.

Suggested $10 donation

Website

The Magnificent Mile Art Fest

10 a.m.-5 p.m. May 30-31

875 N. Michigan Ave.

60 juried artists from around the country will be showcasing a variety of media in this Downtown fine arts fest. Admission is free.

Free

Website

Maifest in Lincoln Square. Credit: Flickr/Rudolf Fink

Maifest Chicago

May 29-June 1

N. Lincoln Ave. and Western Ave.

Join the celebration of German culture with authentic food, live bands, dancing and more at the three-day festival open to all ages.

Free

Website

Mud City Improv Fest

June 4-6

Various locations

You can catch improv across 10 of Chicago’s comedy clubs in this three-day festival. There will be improv acts all weekend at different locations, with tickets ranging from free-$15.

Free-$15

Website

Chicago Blues Festival

June 4-June 7

Millennium Park, 201 E. Randolph St., and Ramova Theatre, 3520 S. Halsted St.

The Chicago Blues Festival is the largest blues festival in the world, and brings annual jams featuring some of the best in genre to Milennium Park, with Taj Mahal slated as this year’s headliner. Festivalgoers can also check out the Blues Village pop-up in Wrigleyville, and attend a pre-festival panel discussion and performance at Ramova Theatre.

Free

Website

Rib Fest

June 5-7

Lincoln Avenue between Irving Park Road and Berteau Avenue

More than 20 of Chicago’s top barbeque vendors are headed to North Center to serve up ribs and sides as they compete for a Ribfest Chicago title. There will also be live music, a kid zone with activities and whiskey/bourbon tastings.

Suggested $10 donation

Website

Festival Del Niño

June 6

Harrison Park, 1824 S. Wood St.

Celebrate Día del Niño with the National Museum of Mexican Art. The Harrison Park celebration will have activities like live music, face painting, skateboarding lessons, giveaways and more. There will also be resources available from organizations like Pilsen Wellness Center. This event is free to attend.

Free

Website

Lincoln Park Greek Fest

June 6-7

St. George Greek Orthodox Church, 2701 N. Sheffield Ave.

Lincoln Park Greek Fest brings authentic food, music, folk dancing and more to the neighborhood for a weeked celebrating Greek culture. There is a $10 suggested donation upon entry.

Suggested $10 donation

Website

57th Street Art Fair

June 6-7

Between Kenwood and Woodlawn avenues

This beginning-to-summer bash showcases locally made art and live blues music. Browse works by more than 150 artists, plus good vendors and family activities. This event is free.

Free

Website

High Vibes Chicago Fest

2-8:30 p.m. June 7

1850 W. Webster Ave.

This festival celebrates cannabis culture, and brings together the city’s top cannabis brands along with live entertainment, food, premium smoking experiences and more. Tickets are $17.85.

$17.85

Website

Puerto Rican Fest

June 11-14

2800 W. Divison St.

This four-day festival celebrates Puerto Rican culture with live music, dancing, more than 25 rides and delicious food from over 150 vendors. Guests are welcomed to bring chairs and blankets to enjoy the festivities. This event also coincides with the Puerto Rican People’s Day Parade on June 13. Tickets start at $18.18.

$18.18+

Website

Andersonville Midsommarfest

June 12-14

Clark Street from Foster Avenue to Gregory Street

Midsommarfest is celebrating 60 years in Andersonville with live performances across five different stages all weekend. Catch performers like Anthony Rapp, Dancing Queen: An Abba Salute, Lucy Stoole and more. There will also be food and drink available for purchase and an artisan vendor market. There is a $10 suggested donation upon entry.

$10 suggested donation

Website

Puerto Rican People’s Day Parade

Noon June 13

Divison Street from Western to Sacramento avenues

The 48th Puerto Rican People’s Day Parade — a part of Humboldt Park’s Puerto Rican Fest — will have Bomba y Plena performances, Parrandas and other celebrations as it flows into the park.

Free

Website

Fans cheer as the Chicago White Sox win their last home game of the season on Sept. 26, 2024, avoiding breaking the MLB loss record. Credit: Colin Boyle/Block Club Chicago

Sox Crawl

June 13

Rate Field, 333 W. 35th St.

Explore the White Sox stadium in a pre-game crawl before the team takes on the Los Angeles Dodgers. The package includes a lower-level ticket to the game, a Sox alumni meet-and-greet, special menu items and more. This event is for people 21 and older. Tickets start at $46.

$46+

Website

Shedd Pride Night

6-10:30 p.m. June 13

Shedd Aquarium, 1200 S. DuSable Lake Shore Drive

Celebrate Pride Night at the Shedd, with a celebration alongside the aquatic animal world. There will be DJs, ocean-themed drag and more. This is a 21-and-older night. Tickets are $29.95 and $19.95 for Shedd members.

$29.95

Website

Old Town Art Fair

June 13-14

Old Town Triangle Center, 1763 N. North Park Ave.

More than 200 artists will be showcasing their work in Old Town for the ultimate art fair. There will be a garden walk, live music, a food court and a children’s area. There is a $13 suggested donation for adults.

$13 suggested donation

Website

Wells Street Art Festival

June 13-14

North Wells Street from North Avenue to Division Street

This art fair will feature more than 100 artists, festival food and live music for a summer weekend celebration. There is a $10 suggested donation upon entry.

$10 suggested donation

Website

Juneteenth Celebration

10 a.m.-8 p.m. June 19

DuSable Black History Museum and Education Center, 470 E. 56th Place

The DuSable Black History Museum and Education Center is hosting its annual Juneteenth celebration with an all-day celebration featuring live music, wellness activities, a local vendor market, educational and cultural programs, family fun and more. This is a free event.

Free

Website

Motoblot: Motorcycle Street Rally

June 19-21

Halsted Street from 35th to 37th streets

Motoblot celebrates motorcylce and hot rod culture with live music, a motorcycle and hot rod street show, group rides and more. Tickets are $20.47 for a daily pass or $50.28 for a three-day pass.

$20.47-$50.28

Website

Bronzeville’s 6th Annual Juneteenth Celebration

10 a.m.-3 p.m. June 20

3500 S. King Drive

Celebrate Juneteenth in Bronzeville with a festival featuring live music, a small business vendor market, family fun and a special recognition honoring Father’s Day. The theme for this year’s celebration builds on last year’s theme of “Honoring the Legacy of Freedom: Remembering the Past Inspiring the Future.”

Free

Website

Fiesta Back Of The Yards

June 19-21

Ashland Ave from 45th to 47th Street

This three-day festival brings live entertainment, carnival rides, Latin cuisine, games to Back of the Yards to showcase the culture and history of the neighborhood.

$75 for 3-day writstband

Website

Chicago Food Truck Festival

June 20-21

2300 S. Indiana Ave.

Enjoy gourmet eats, live music and Daisy margaritas from the Chicago Margarita festival. Tickets are free, and $12.51 for VIP admission.

Free-$12.51

Website

Gold Coast Art Fair

June 20-21

Grant Park’s Butler Field, 235 S. Columbus Drive

The Gold Coast Art Fair is returning to Grant Park for its 68th year, and will feature over 200 artists from across the country. Browse paintings, scultpures, jewelery, ceramics and more. There will also be food and drinks, plus activities like henna and paint & sip. Tickets are $12.51.

$12.51

Website

Mark King is dressed up for Pride Fest on June 19, 2022 outside of the Center on Halsted. Credit: Kathleen Hinkel/Block Club Chicago

Pride Fest

June 20-21

Halsted Street from Addison to Grace streets

The annual Northhalsted Pride Fest will have live music across three different stages, drag performances, a pet parade, guest speakers and more. There is a suggested $20 donation upon entry.

$20 suggested donation

Website

San Juan 5K

8:30 a.m. June 21

2800 W. Divison St.

Support Tu Casa Project, a local organization that provides youth programs, financial education and more, by running or walking a 5K through Humboldt Park. Registration starts at $45 for adults and $30 for youth runners, ages 12 and under.

$30-45

Website

Flavors of Albany Park

June 24

North River Commission, 3403 W. Lawrence Ave.

Explore one of Chicago’s most diverse neighborhoods with a celebratory food crawl honoring Albany Park’s community, culture and connection. There will be samples available from more than 60 neighborhood restaurants. Tickets are $45 for adults, and $30 for kids and seniors.

$30-45

Website

Malt Row Damen Beer Stroll

5-30-8:30 p.m. June 24

Damen Avenue between Wilson Avenue and Argyle Street

Discover more of Ravenswood as local breweries pair with neighborhood businesses for an evening of beer, spirits, wine and local shopping. Tickets include more than 12 tasting pours and are $32.

$32

Website

Chicago Taco & Tequila Fest

June 26-27

2555 N. Ashland Ave.

Try local taco spots and tequila samples at Tequila Fest. Tickets are $15.

$15

Website

Michelada Fest

June 26-28

Union Park, 1501 W. Randolph St.

This annual summer festival combines music, miches and community for the ultimate celebration of Latino culture. This year’s headliners include Latin Mafia, Jhayco, Jessie Reyez and more. Plus — Friday is community day, where admission to the festival is free. Find more about Saturday and Sunday ticket options here.

$0-373.05

Website

Moloko Ukrainian Festival

June 27-28

Copernicus Center, 5216 W. Lawrence Ave.

This outdoor festival celebrates modern Ukraine through music, authentic cuisine and more. Tickets start at $36.70.

$36.70+

Website

Back Lot Bash Chicago Pride

June 27-28

Cheetah Gym, 5248 N. Clark St.

The 22nd annual Back Lot Bash is back for Chicago Pride weekend with headliners like Lauren Sanderson, DJ Cash Era and more. Tickets are $25.27 and can be purchased here.

$25.27

Website

Millennium Art Festival

June 27-28

180 N. Stetson Ave.

Stop by this art festival to browse works from over 110 different artists and enjoy food trucks, live music, kid-friendly art tents and more. Entry is free.

Free

Website

Jeniyah poses for a photo during the 54th annual Chicago Pride Parade in Lakeview on June 29, 2025. Credit: Colin Boyle/Block Club Chicago

Chicago Pride Parade

11 a.m. June 28

Starts at 3900 N. Broadway

The 55th annual Chicago Pride Parade will take over the North Side during the last weekend of June with floats, music, performances and more. This parade is free to attend.

Free

Website

African/Caribbean International Festival of Life

July 3-5

Union Park, 1501 W. Randolph St.

This cultural festival celebrates music, food, arts and culture of the Caribbean, Africa and other regions. There will be live music, an international food marketplace, performances and more. Tickets are $20.

$20

Website

4th On 53rd Parade & Festival

11 a.m.-3 p.m. July 4

Starts at Hyde Park Bank, 1525 E. 53rd St.

This Hyde Park tradition features marching bands, floats and more as the parade leads into a free festival with performances, games, bouncy houses, face painting, a magician and more. This is a free event.

Free

Website

Pride South Side Festival

2-10 p.m. July 5

The DuSable Museum, 740 E. 56th Place

Pride South Side is celebrating the Black LGBTQ+ community with their eighth annual Love in Action pride fest. There will be live music, local art, resource hubs and more. This is a free event.

Free

Website

Windy City Smokeout

July 8-12

United Center Parking Lot, 1901 W. Madison St.

This five-day country music and barbecue festival will feature performers Hootie & the Blowfish, Treaty Oak Revival and more. Browse ticket options from $65-$300 here.

$65-$300

Website

The Jason family dines during the Taste of Chicago in Grant Park on Sept. 9, 2023. Credit: Colin Boyle/Block Club Chicago

Taste Of Chicago – Grant Park

July 8-12

Grant Park, 331 E. Randolph St.

Enjoy Chicago’s best eats on the lakefront Grant Park during the 46th annual Taste of Chicago festival. This is a free event.

Free

Website

Square Roots

July 10-12

Lincoln Avenue between Montrose and Wilson avenues

Square Roots is returning to Lincoln Square for a weekend of live music, family fun, local restuarants and vendors, plus craft beer and cocktails. There is a $10 suggested donation for this event.

$10 suggested donation

Website

The Chosen Few Picnic & Music Festival

7 a.m.-10 p.m. July 11

Jackson Park, 6401 S. Stony Island Ave.

Enjoy live music all day long at The Chosen Few Festival, which is often dubbed the “Woodstock of House Music.” The celebration is entering its 36th year and will feature a wide lineup of DJs, and plenty of areas to listen and dance. Tickets are $89.94 for general admission.

$89.94

Website

Southport Art Fest

July 11-12

3733 N. Southport Ave.

Stroll Southport Corridor during this art festival featuring a lineup of 100 artists, eats from local restuarants, family fun and more. Admission is free.

Free

Website

Horner Brew Fest

6-10 p.m. July 17

Horner Park, 2751 W. Montrose Ave.

There will be craft beer tastings, food trucks and live music in Horner Park. This event is for people 21 years of age or older. Tickets start from $43.61 .

$43.61+

Website

Taste Of River North

July 17-18

Wells Street between Ontario and Superior streets

Explore the River North culinary scene with gourmet bites. The two-day celebration will be complete with live music, vendors, interactive experiences, family fun and more.

Website

Roscoe Village Burger Fest

July 17-18

2000 W. Belmont Ave.

Chicago’s top eateries come together at the annual Roscoe Village Burger Fest to serve up their most creative takes on the classic burger. Plus, there’s live music across two stages, art vendors, a family zone and the “Best Burger Competition,” which will crown one business as the ultimate burger champion. There is a $10 suggested donation upon entry.

Suggested $10 donation

Website

West Fest

July 17-19

Chicago Avenue between Wood Street and Damen Avenue

This annual festival in West Town features a live music lineup programmed by Empty Bottle. There will also be food and retail vendors, a kid fest with pony rides, bounce houses and more plus a pet fest to celebrate the furry friend neighbors of West Town.

Suggested $10 donation

Website

Ravenswood On Tap

July 18-19

Ravenswood and Berteau Avenues, Ravenswood Corridor

Malt row in Ravenswood is one of the most vibrant brewing communities in the country. Ravenswood on Tap celebrates local breweries in a two-day festival with beers from breweries along malt row, KOVAL cocktails, live music, street food, axe-throwing and more. There is a suggested $10 donation for this event.

Suggested $10 donation

Website

Taste Of Lincoln

July 24-26

2500 N. Lincoln Ave.

Catch live muisc, food from local vendors, whiskey tasting, arts and crafts, a kids’ carnival and a dog parade as Taste of Lincoln returns for its 42nd year along Lincoln Avenue. There is a suggested $10 donation upon entry.

Suggested $10 donation

Website

Chicago Gospel Festival

July 24-25

Millenium Park – Pritzker Pavilion, 201 E. Randolph St.

The Chicago Gospel Festival is returning to Millennium Park to celebrate the power of music with a wide lineup of acclaimed gospel singers. Admission is free to this event.

Free

Website

Wicker Park Fest on Milwaukee Avenue. Credit: Provided

Wicker Park Fest

July 24-26

1165 N. Milwaukee Ave.

Wicker Park Fest celebrates summertime Chicago with the ultimate three-day music festival. Catch an eclectic lineup of musical acts and enjoy food options, arts and culture performances and more. There is a $10 suggested donation upon entry.

Suggested $10 donation

Website

Black & Brown Femme Film Festival

July 24-25

Logan Center for the Arts, 915 E. 60th St.

This two-day film festival centers Black and Brown femme voices in the filmmaking space. There will screenings of 43 films, panels and other special events. Tickets start at $17.85.

$17.85+

Website

Chinatown Summer Fair

July 25-26

Wentworth Avenue from Cermak Avenue to 24th Place

The Chinatown Summer Fair is a neighborhood celebration with food, music, peformances and more. The festival will kick off with a lion dance, followed by kung fu demonstrations, samples from Chinatown’s best restuarants and more. This event is free to attend.

Free

Website

The hallway inside the Promontory Point business car, which was built by Pullman in 1953 for Union Pacific Railroad, at the grand opening of the Pullman National Monument on Sept. 3, 2021. Credit: Colin Boyle/Block Club Chicago

Pullman Railroad Days

July 25-26

Pullman Exhibit Hall, 11141 S. Cottage Grove Ave.

Pullman Railroad Days celebrates trains, technology and more at Pullman National Historical Park. There will be exhibits, railcar tours, demos and pop-ups, live music and more. Tickets start at $17.85.

$17.85+

Website

Lollapalooza

July 30-Aug. 2

Grant Park, 331 E. Randolph St.

The highly anticipated four-day music festival is back in Grant Park with headliners like Lorde, Charli XCX, John Summit, the Smashing Pumpkins and more. There’s also a special kids stage and food across the festival grounds. Lots of ticket options are sold out, but Sunday general admission options are still available.

$329+

Website

Italian Beef Fest

July 31-Aug. 2

4822 N. Long Ave.

The Chicago Italian beef fest is honoring Chicago’s most iconic sandwich with a festival featuring some of the city’s favorite spots serving up their take on the beef. Festivalgoers can cast their vote for “Best Italian Beef Sandwich.” There will also be two stages of live music, a kids zone and more.

Admittance is free.

Website

Bronzeville Smooth Jazz Festival

Noon-8:30 p.m. Aug. 1

3702 to 3837 King Drive

This hyperlocal jazz festival brings music, performances, food and local vendors to Bronzeville. This is a free festival.

Free

Website

Black & Bronze: A Bronzeville Music Fest

1-7 p.m. Aug. 29

Armstrong (Lillian Hardin) Park, 4433 Saint Lawrence Ave.

Celebrate the legacy of Bronzeville with this festival that includes live music, performances, exhibitions, a dunk contest, pilates, a kid zone and more. Entry is free before 2:30 p.m. and $12.51 after.

Free-$12.51

Website

Northalsted Market Days

Aug. 7-9

Halsted Street from Belmont Avenue to Addison Street

This three-day festival celebrates the Northalsted/Lakeview neighborhood with four stages of live music, more than 250 vendors, drag performances, dance exhibitions plus food and drink. There is a $20 suggested donation upon entry.

Suggested $20 donation

Website

A member of the Bud Billiken performing art league dances during the 96th anniversary of the Bud Billiken Parade – the largest Black parade in the country. Saturday, Aug. 9, 2025. Credit: Sebastián Hidalgo for Block Club Chicago

Bud Billiken Parade

10 a.m.-4 p.m. Aug. 8

4500-5500 blocks of South Martin Luther King Drive

Bud Biliken, the parade that celebrates Black Chicago with a two-mile parade, will feature music, dance. food, back-to-school giveaways and more. This is a free event.

Free

Website

Ecuadorian Parade

Noon Aug. 10

Montrose and California avenues to Kimball Avenue

This parade celebrates Ecuadorian culture, independence and more with a parade, dancing and music. This is a free event.

Free

Website

Pakistan Independence Day Parade

Noon Aug. 10

Devon Avenue from Damen to California avenues

The Pakistan Independence Day Parade will run down Devon Avenue, Chicago’s South Asian ethnic enclave, and will have floats, music and more.

Free

Website

Race Judicata

6:30 p.m. Aug. 13

1764 N. Stockton Drive

This 5K run/walk supports Chicago Volunteer Legal Services and celebrates its 30th anniversary. Registration starts at $40.

$40-45

Website

Victor Hilitski, freelance photojournalist for Block Club Chicago, tandem jumps over Chicago with the U.S. Army Golden Knights parachute team on Aug. 17, 2025. Credit: Megan Hackett | U.S. Army Parachute Team Media Relations

Chicago Air & Water Show

10:30 a.m.-3 p.m. Aug. 14-16

North Avenue Beach, 1601 N. DuSable Lake Shore Drive, and along the lakefront

One of Chicago’s most popular summertime activities is lifting off again in August with two days of aerial demonstrations. There will also be rehearsals before the festival starts, making it the largest free air and water show in the nation.

Free

Website

Chicago House Music Festival & Conference

Aug. 27-30

Chicago Cultural Center, 78 E. Washington St., and other locations

Learn from Chicago house music icons and experts in the birthplace of the genre with a three-day, multi-venue panel. Admission is free.

Free

Website

Lakeview Taco Fest

Aug. 21-23

3500 N. Southport Ave.

The 13th annual Lakeview Taco Fest celebrates the neighborhood’s restuarants and community. Over 10 businesses will be serving up tacos along with beer pairings. Plus, there’s live music, a lucha libre showcase and more. There is a $10 suggested donation upon entry.

Suggested $10 donation

Website

VillaPalooza

Aug. 22

La Villita Park, 2800 S. Sacraemtno Ave.

This free music festival is in the heart of Little Village and will feature music, art, food and more.

Free

Website

Supertri Chicago

Aug 22-23

Starts at Lake Michigan and ends in Grant Park

Bike, run and swin through some of Chicago’s most iconic destinations in the Chicago triathlon. There are also race options for kids and varying levels of ability. Register for free if you’re a part of a relay team or register for individual competion for $176.

Free-$176

Website

Taste Of Greektown

Aug. 28-30

315 S. Halsted St.

West Loop’s vibrant Greek restaurant scene will be serving up the best of Mediterranean flavors in this three-day festival complete with live traditional music, family fun and more.

Free

Website

Panda Fest

Aug. 28-30

Upper Hutchinson Field – Grant Park, 200 E. Balbo Drive

Panda Fest is making its Chicago debut in August. The viral Asian food and culture fest will head to Grant Park for a weekend of food, merchandise, panda-inspired interactions, performances and more. Tickets start at $12.79.

$12.79+

Website

Black & Bronze: A Bronzeville Music Fest

1-7 p.m. Aug. 29

Armstrong (Lillian Hardin) Park, 4433 St. Lawrence Ave.

Celebrate the legacy of Bronzeville with this festival that includes live music, performances, exhibitions, a dunk contest, pilates, a kid zone and more. Entry is free before 2:30 p.m. and $12.51 after.

Free-$12.51

Website

ARC Music Festival

Sept. 4-7

Union Park, 1501 W. Randolph St.

Enjoy house and techno music as ARC brings a huge lineup of artists to Union Park. Single-day passes start at $169.

$169-$549

Website

Taste Of Polina

Sept. 4-7

Copernicus Center, 5216 W. Lawrence Ave.

The largest Polish festival in the country is back over Labor Day weekend, stretching across three blocks with live music, a kids stage, exhibitions showcasing Polish culture and more. Single day tickets are $15 and four-day passes are $45.

$15-45

Website

Chicago German-American Oktoberfest

Sept. 5-7

4521 N. Lincoln Ave.

Celebrate German culture with food, drinks, live music and more. Admission is free.

Free

Website

Von Steuben German Day Parade

2 p.m. Sept. 12

Lincoln Avenue and Irving Park Road to Eastwood, West to Western, then to Lawrence Ave.

This parade continues Oktoberfest celebrations in Lincoln Square with a parade through the neighborhood.

Free

Website

Printers Row Lit Fest

Sept. 12-13

South Dearborn Street, from Ida B. Wells Drive to Polk Street

The largest free outdoor literary event in the Midwest is back in September, where literature lovers can browse books, attend author events and more. All events are free.

Free

Website

El Grito Chicago

Sept. 12-13

350 E. Monroe St.

El Grito is a Mexican Independence Day celebration that brings live music, authentic music and plenty of activities Downtown for a celebration of Mexican heritage. Tickets start at $9.

$9+

Website

Ravenswood Art Walk

Sept. 12-13

Ravenswood Industrial Corridor, Lawrence Avenue to Irving Park Road

Explore Ravenswood with an outdoor art walk featuring workshops, performances, a beer garden and food trucks, kids activities and live, local music — all for free.

Free

Website

Women dance in the 26th Street Mexican Independence Day Parade in Little Village on Sept. 14, 2025. Credit: Anastasia Busby/ for Block Club Chicago

26th Street Mexican Independence Day Parade

Noon Sept. 13

26th Street from Albany to Kostner avenues

Celebrate Mexican Independence Day in Little Village with a parade through the vibrant neighborhood.

Free

Website

87th Annual Mexican Independence Day Parade

Noon Sept. 14

Commerical Avenue from 87th to 100th streets

This annual parade celebrates Mexican culture and independence in South Chicago. This event is free to attend.

Free

Website

Retro On Roscoe

Sept 18-20

2000 W. Roscoe St.

This festival is focused all things throwback, with live music, classic car shows, vintage shopping and more. There will also be food, craft beer and family activities. There is a $10 suggested donation upon entry.

Suggested $10 donation

Website

Riot Fest

Sept. 18-20

Douglass Park, 1401 S. Sacramento Drive

Riot Fest is headed back to Douglass Park for a three-day punk rock, alternative, hip-hop and reggae music festival. Presale tickets are already available.

Presale tickets start at $319.98

Website

Lakeview Festival Of The Arts

Sept. 19-20

Broadway from Belmont Avenue to Hawthorne Place

The Lakeview Festival of the Arts brings more than 150 artists to the neighborhood for an art fair complete with live music, local cuisine and family activities. There is a suggested $5 donation upon entry.

Suggested $5 donation

Website

World Dumpling Fest

Sept. 19-20

2555 N. Ashland Ave.

Enjoy dumplings from a variety of cuisines in the 6th annual Dumpling Fest. There will also be a craft vendor market.

Free

Website

Oktoberfest Chicago

Sept. 25-27

1429 W. Wellington Ave.

Close out summer and welcome fall with Oktoberfest — a three-day celebration of German culture and cuisine. Enjoy live music, beer, brats, polka dancing and more. There is a $10 suggested donation upon entry.

Suggested $10 donation

Website

Hyde Park Jazz Fest

Sept. 26-27

Midway Plaisance Park, 1130 Midway Plaisance

The Hyde Park Jazz Fest is celebrating its 20th year in the neighborhood with the ultimate weekend of jazz.

Free

Website

WingOut Chicago

Sept. 26-27

Gallagher Way, 3635 N. Clark St.

This food festival brings together Chicago’s best wing spots with samples, live music, drinks and more. Tickets start at $26.64.

$26.64

Website

Jerk, Seafood & Vegan Festival

Sept. 26-27

Union Park, 1501 W. Randolph St.

This end-of-summer festival will have food, drinks, music, games and more.

$12.51

Website


‘ The preceding article may include information circulated by third parties ’

‘ Some details of this article were extracted from the following source blockclubchicago.org ’

Tags: Guide to Chicagothings to do
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