The Ultimate Chicago Summer Festival Guide 2019

Whether this is your first summer in Chicago or your 100th summer in the city, this summer festival guide is your-go to agenda for everything happening this summer. And I mean everything. With over 80 different event listings, this guide features everything from music and street festivals, to free events that are perfect for families and solo travelers visiting the city this summer. They call it “Summertime Chi” for a reason—see below to find out why.

Need to plan an outing in July? Looking for your favorite fall event? Jump ahead by following the links below.

May

June

July

August

September

Music Festivals

Summer Long Festivals


Neighborhood Festivals

May

The Chicago House Music Conference and Festival by  Chicago DCASE featured on The Haute Seeker
The Chicago House Music Conference and Festival | Photo by Chicago DCASE

May 23rd – 25th: The Chicago House Music Conference and Festival. House music revolutionized dance music internationally. The festival, celebrating the Chicago born genre will feature an industry gathering, DJs and live performances showcasing the various sounds and styles of house music. Admission is free to both the festival and conference. For more details on this event, visit the website.

May 25th – 26th: The Belmont Sheffield Music Festival. One of the opening festivals to the summer season. Celebrating its 35th year with great music shows on two different stages. Free admission, $5 suggested donation. Get more details here.

May 31st – June 2nd: Do Division Street Fest. The is a major festival that kicks off summer in Chicago. Live music takes place on two stages programmed by the famous music venues Subterranean and The Empty Bottle, along with a wide variety of local food and beverage vendors. Do Division also features a dedicated Family Fun Fest area. Plus DO Fashion, fashion-forward activities taking place throughout the weekend, including a runway shows and more. Free admission, $10 suggested donation. For more details visit the event page.

May 31st – June 2nd: Lincoln Park Greek Fest. Authentic Greek cuisine, music, dance performances, kids’ activities. Of course, all with Hellenic pride showcased outside of St. George Greek Orthodox Church. Free admission. For more details, visit the website.

May 31st – June 2nd: Taste of Mexico. The Taste of Mexico in Little Village is a South West side neighborhood favorite. The fifth annual festival takes place on 26th street and showcases some of the best Mexican food in the city. In addition to the authentic food from nearly 20 neighborhood restaurants, there will also be non-stop music and entertainment as well as arts & crafts focusing on Mexican culture. Free admission. For details on the event, visit the website here.

June

57th Street Art Fair on The Haute Seeker
Image | 57th Street Art Fair

June 1st – 2nd: 57th Street Art Fair. The annual two-day outdoor celebration of visual arts takes places the first full weekend in June. Artists and art lovers convene at Chicago’s oldest juried art fair in the Midwest to view work of up to 200 exhibitors. Admission is free. Check out more details of this highly anticipated art show here.

June 1st – 2nd: Gold Coast Art Festival. Recognized as the “Granddaddy of American Art Festivals” the Gold Coast Art Festival is the mecca for art collectors and admirers during the summer in Chicago. Grant Park welcomes more than 300 artists from around the world to downtown Chicago featuring exceptional artwork, demonstrations, immersive project, and more. Admission is $10, children 13 and under are free. Find more details on the 62nd annual fair by visiting the website.

June 7th – 9th: Andersonville Midsommarfest. The festival celebrates the old-world Swedish traditions in Andersonville. Chicagoans gather along Clark Street between Foster and Catalpa for a three-day festival that is full of music, dancing, kids entertainment, and tasty international food. Suggested $10 donation, kids under 12 and seniors are free. For more details on this festival, visit the website.

June 8th – 9th: Pilsen Food Truck Social. Located in the culturally rich Lower West Side neighborhood of Pilsen, the food truck social features over a dozen popular food trucks, local restaurants, and retail vendors. In addition to the food trucks, the popular event will host a mix of live music and local performances as well as other live entertainment. Admission is $5 optional donation. For more details on this festival, visit the website.

June 8th – 9th: Wells Street Art Festival. Find the next art piece for your home at the art extravaganza in the historic Old Town neighborhood. The art festival features work by more than 200 juried artists from across the nation. Admission is a suggested $8 donation. Check out full event details here.

June 8th – 9th: Printers Row Lit Fest. Book lovers, Zine-o-philes, and literary collectors flock to the Printers Row Lit Fest every year Chicago. Now in its 35th year, the Printers Row Lit Fest returns with even more book dealers. All-free programs, a kids favorite book character costume parade, plus more literary activities that you will not find anywhere else this summer. Admission is free. For details, visit the website here.

June 14th – 16th: Taste of Randolph Street. The popular street festival feature brings together good vibes, and the well-known restaurants on Randolph St. Over sixteen excellent restaurants bring irresistibly unique flavors along with the sounds of the nation’s hottest up-and-coming bands and musicians. Admission to the festival is a suggested $10 donation. For more details, visit the website.

June 15th: Chicago Taco & Tequila Fest. Tacos + Tequila = a match-mate in festival heaven. The festival features traditional and exotic in ingredient-stuffed tortillas paired with tequila-infused cocktails. Plus, margarita flights, tasting, along with living bands and other entertainment. This event is 21+. Tickets range from $10 – $40 and include one complimentary margarita. For more information, visit the event page. Find a deal on tickets by following this link.

Begyle Brewing Company in Ravenswood featured on The Haute Seeker
Begyle Brewing Company | Photo by Ravenswood Chamber of Commerce

June 22nd – 23rd: Ravenswood On Tap. Experience “Malt Row” home to one of the country’s most well-known craft brewing communities this summer in Chicago. Home to Ravenswood On Tap, the craft beer festival features beer and spirits from local breweries, grub from some of Chicago’s favorite restaurants and food trucks, a killer lineup of live music, and handmade goods from local retailers and artists. Get more details on the event by visiting the website here.

June 28th – 30th: Logan Square Arts Festival. The free festival is located in Monument Park in Logan Square. The event features three days of live music, visual art, performance art, dance, food, and drinks. For more details, visit the website.

June 28th – 30th: Millennium Art Festival. The three-day weekend festival is a top-ranked art and design show in Millennium Park. The festivals showcase an array of artwork from painting to photography to furniture and ceramics. A juried show blending live performances treats interactive art experiences and more. This event is free and open to the public. For more details, visit the website here.

July

July 4th – 6th: Windy City Ribfest. Smokey, savory, and saucy BBQ pairs with lively entertainment. The three-day event takes places during 4th of July weekend in Uptown. Suggest donation of $5. For more details, visit the website here.

Festival of Life-Chicago Festival-Taylor Justin-The Haute Seeker
Image | Festival of Life

July 4th – 7th. The International Festival of Life. Dedicated to the diverse culture and music primarily from the Caribbean, Africa, Latin America, and the United States. The festival brings people and communities together through music, culture, and the celebration of life. Stay up to date with festival details by visiting the website.

July 5th – 7th: West Fest. The annual street festival takes place in Chicago’s West Town community and reflects the elective and colorful neighborhood. The festival features live music, DJs, as well as separate areas for both children and pets. A $5 donation is suggested. Making this festival enjoyable for the whole family. Get more details on the festival by visiting the website here.

July 6th: Chosen Few DJs Picnic. Born, nurtured, and developed in the South Side neighborhood of Jackson Park, the Chosen Few Picnic is a summer staple in Chicago. The well-known picnic celebrates and honor “House Music”—an original genre of Chicago. Tickets vary between $125 – $450. For tickets and more information, visit the website here.

July 10th – 14th: Taste of Chicago. Taste of Chicago is the nation’s premier free outdoor food festival showcasing the diversity of Chicago’s dining scene, alongside a smorgasbord of cooking demonstrations, music concerts, dance performances, art activations, family activities and more. For more details, visit the website.

July 12th – 14th: Square Roots Festival. The craft beer-focused festival pairs Lincoln Squares finest restaurants with over 40 regional craft breweries. The festival boasts 70 acts on four stages, craft beer, food, and more. The festival that is perfect for families of all backgrounds. Suggested donation is $10 for adults, $5 seniors/kids, and $20 for families. For more details, visit the website here.

July 13th – 14th: Roscoe Village Burger Fest. Savor burgers from over a dozen local restaurants in Roscoe Village. In addition to the flame-broiled burgers are two stages of non-stop music, a Kid’s Zone, artists, merchants, and more. For more details, visit the website.

July 19th – 20th: Artfest Michigan Avenue. An intimate fine art fair showcase 65 juried artists. The festival takes place on the famous Michigan Avenue at the based of the iconic Tribune building. The event is free. Visit the website for a list of participating artists here.

July 19th – 20th: BenFest. The family fun festival that is perfect for small kids includes excellent bands, local cuisines, and plenty of activities for kids including inflatables, Blackhawks Hockey Hot Shot, Super Giant Tic Tac Toe and Connect 4, and more. Admission is $5 donation, kids 5 and under are free. For more details on the festival, visit the website here.

July 19th – 21st: Columbian Fest/ El Gran Festival Colombiano. The ultimate festival for Columbian culture in Chicago. Columbian Fest is a three-day event featuring 8 acres of non-stop music, food, and culture. Admission is $10 – $25. To purchase tickets and to view the full lineup of entertainment, vendors, and more, visit the website here.

July 19th – 21st: Taste of River North. Sample some of River North’s most dynamic, restaurants, delicious drinks, and more. Visit the festival website for details on participating vendors. Admission is a $5 donation.

July 19th – 21st: Tacos Y Tamales. The Pilsen street fair takes inspiration from traditional market known as Tianguis; where authenticity is at the forefront for food, drink, music, shopping, & more. $5 Donation. Tickets to the tequila tasting available here.

July 20th – 21st: Chicago Craft Beer Festival. The brewery-focused festival features 70 specialty beers crafted by 35+ local, regional, and national breweries. Ticket holders will be in hops heaven during this festival. Tickets range between $20 – $60 and include up to 20 tickets, souvenir glass, live music, and a seating area. To purchase tickets, visit the event page here.

chicago-silver-room-block-party-by Taylor Justin of The Haute Seeker
Silver Room Block Party | Photo by Taylor Justin

July 20th: 16th Annual Silver Room Block Party. The outdoor celebration of music, community, art, love, and culture attracts a diverse crowd from all parts of the city and country. This big event was mentioned in the best Chicago events. Admission is free. More details are available here.

July 21st: Chinatown Summer Fair. The iconic event celebrates the beauty of the Far East and culture. The festival opens with a lion dance procession followed by Asian performances and entertainment, samplings from Chinatown’s restaurants, unique gifts, arts crafts, street vendors, and more. Free admission. Check out more event details on the website.

July 26th: Lincoln Park Wine Festival. Experience Lincoln park after dark of red wines and sweet rosés. Savor more than 35 different varieties of wine at Lincoln Park Zoo’s annual Summer Wine Fest. Guest will enjoy a summer evening of wine tastings and music amid the zoo’s lush gardens at this after-hours event. Tickets are $20 – $79. This is a 21+ only event. To purchase tickets and for more details, visit the website.

July 26th – 28th: GhanaFest. The 31st anniversary of GhanaFest is the largest summer showcase of Ghanaian music, art, fashion, food, performances and culture in the Midwest. Don’t miss out on this historical celebration. Be sure to visit the website here.

July 27th – 28th: Taste of Lincoln Avenue. Now in its 36th year, the festival takes over neighborhood blocks for a festival that is perfect for both children and adults. Admission is free, with a suggested $10 donation. For more details, visit the website here.

July 27th – 28th: Bantu Fest. The 5th annual Bantu Fest is a community festival bringing together over 30 different countries and cultures together to celebrate diversity, unity, and love. Enjoy food, arts, music, vendors, and more at this international festival at Midway Plaissance. Day passes range from $5 – $10. For tickets, visit the website here.

August

August 2nd – 4th: Jeff Fest. There’s something for everyone, every genre at Jeff Fest, the northwest side neighborhood of Jefferson Park. The highly anticipated music festival features cutting edge local and national acts fill out a jam-packed weekend. Admission is $5 a day. Get more details on the website.

August 10th – 11th: Northalsted Market Days. Celebrate the life and community of the historic Boystown/Lakeview district this summer in Chicago. Northalsted Market Days is a 1/2 mile long festival featuring all-day lineups of live music on 5 stages, 200+ unique vendors, arts, crafts, food and drink, DJ’s and dancing, sponsor booths, and more. $10 suggested donation. Visit the website for more details on this vibrant celebration.

August 15th – 18th: Chicago’s Little Italy Festa. Italian Ice, Cannoli, Zeppole, Pasta, and more line Taylor St. this August in Chicago at Chicago’s Little Italy Festa. The annual street festival celebrates the history of the neighborhood through food from award-winning area restaurants, music, and family-friendly entertainment. For more details on this event, visit the website here.

August 17th: West Side Music Fest. The Chicago Westside Music Festival(“WSMF”) is an annual music festival that takes place in Douglas Park on the West Side of Chicago. WSMF fills the void of cultural programming and outlets available to residents on the West Side of Chicago and is recognized as a destination for music and summer festival fun. Admission is free. Check out the event lineup and more here.

August 17th – 18th: 61st Annual Chicago Air and Water Show. The Air and Water show features military and civilian flight aerobatics, historic aircraft, simulated water rescues, and parachute teams, the Chicago Air and Water Show is one of the largest and longest-running free admission events of its kind. For more information, visit the website here.

August 17th – 18th: Wicker Park Fest. Building on the area’s unique character, the weekend celebrates the neighborhood with eclectic music (over 50 bands on four stages), great local food, arts and crafts, a kids’ area, and retail vendors. Admission is free, $10 suggested donation at the gate. Get more details on this festival here.

August 17th – 18th: Sangria Festival Chicago. The fourth annual festival brings together the art of Sangria paired with a variety of cuisine. Sip sangria in Humboldt Park, rock to the sounds of live world music, dancers, and more. This event is 21+ with tickets ranging between $15 – $65. To purchase tickets, visit the website here. Salud!

August 17th – 18th: 64th Annual Ginza Holiday Festival. Ginza Holiday Festival is a celebration of Japanese and Japanese-American food, art, culture, and entertainment. One of the most unique features of this special is The Waza, a select group of over 100 artisans skilled in traditional crafts dating back to Japan’s Edo Period, 300 years ago. Admission is a $5 donation, children 12 and under are admitted for free when accompanied by an adult. For more details, visit the website here.

August 17th – 18th: Taste of Greektown. Sample some of the best Greek food and culture you can find in the Chicagoland area. Home to iconic dishes such as the Kronos made Gyro, Taste of Greek town is the center of Hellenic pride, history, and culture. Admission is free. More information on the event here.

African Festival of the Arts-featured on The Haute Seeker
Image | Africa International House

August 30th – September 2nd: African Festival of the Arts. This annual festival that takes places during Labor Day Weekend on the festival grounds in Chicago’s historical Washington Park. Attendees are transported across the Diaspora with interactive engagements, vibrant drumming, museum-quality collectible artifacts, colorful and rich handwoven fabric and textile, and curated spaces that showcase the art, food, and culture of the Diaspora. Tickets range between $5 – $20. To purchase tickets and to learn more about this festival, visit the website here.

August 30th – September 1st: The Great American Lobster Fest. The Midwest’s largest Lobster and Seafood Festival takes place on Navy Pier during Labor Day weekend. Celebrate the last hurrah of summer with freshly flown in lobster from the East Coast, live music performances, family-friendly games and activities, unique arts/craft shopping, land food options, cold beverages and more. Tickets range from $34 – $99. For more information on the event, visit the website here.

September

September 6th – 8th: Throwback Music Fest. Retro tunes and classic cars fill the Gladstone Park neighborhood on the North West of Chicago. The festival takes place after Labor Day and features music, vibes, and fun inspired by the 50’s, 60’s, and 70’s. Admission is free, $5 suggested donation. For more details, visit the website.

September 7th – 8th: 79th Street Renaissance Festival. The neighborhood festival is the longest-running block party in Auburn Gresham. The South Side festival offers attendees the opportunity to support their local businesses through food, games, entertainment and more. Admission is free. For more details, visit the website.

September 7th – 8th: Chicago Bourbon & Barbecue Fest. Make your way to Roscoe Village for bourbon, bbq, and more post-Labor Day. The finger-lickin’ festival features an afternoon bourbon tastings and plenty of mouth-watering chicken, ribs (and more), there is also one stage of soulful music. Free admission, $5 suggested donation. For tickets to the bourbon tasting and more information on the festival, visit the event page.

September 14th – 15th: Lakeview East Festival of the Arts. For more than 15 years the unique and popular art festival has called the Lakeview East neighborhood home. The arts festival showcases more than 150 juried artists featuring paintings, sculpture, photography, furniture, jewelry and more. A wonderful place to find original pieces for sale at various prices ranges to suit any art lovers budget. Admission is free, $5 suggested donation. For more details, visit the website here.

September 20th – 21st: Norwood Park Fall Fest. This fall event is a family-oriented celebration by day and a music festival by night. The event features live entertainment consisting of various genres, food trucks, and local merchants from across the Chicagoland area. The festival takes place on Northwest Highway this fall. Free admission, $5 suggested donation. For more details, visit the website here.

September 21st – 22nd: Sam Adams’ Lakeview Taco Fest. Taco festivals aren’t just for the summer season. September sizzles with tortilla-wrapped goodness at the 7th annual Sam Adams’ Lakeview Taco Festival. No matter the preference, find your favorite taco at this years festival featuring not only food but specialty beers, live entertainment, Lucha Libre Mexican wrestling, and more. Admission is free with a $10 donation. For more details, visit the website here.

September 27th – 28th: Oktoberfest Chicago. The annual event is one of Chicago’s most popular fall celebrations. The three day festival at St. Alphonsus brings beer, brats, band, and all things Bavarian to the North Side neighborhood of Lakeview. Enjoy additional activities including Kinderfest, music, and more. Admission is free, with a $5 donation. For more details, visit the website here.

September 28th – 29th: Edgewater Arts Festival. If you’re a art lover in the Chicago area, the 7th annual Edgewater Arts Festival is an event to attend this fall. Meet emerging artists and explore the Edgewater neighborhood at this two-day event. Admission is free. Visit the website for more details.

Music Festivals

Chicago Gospel Music Festival. May 31st – June 1st. Chicago Gospel Music Festival. Celebrating the great influence of the music genre born in this city 80 years ago, the Chicago Gospel Music Festival features local and national artists from traditional choirs to contemporary urban styles at the largest free, outdoor gospel music festival of its kind. For more details on this festival, visit the website.

Chicago Blues Festival. June 7th – 9th. Chicago Blues Festival. Celebrating the Chicago Blues’ past, present, and future, the Chicago Blues Festival. The event features the live music performances of over 100 national, international and local artists celebrating the city’s rich Blues tradition. It also shines a spotlight on the genre’s contributions to the soul, R&B, gospel, rock hip-hop, rap and more. Visit the website to learn more about this highly anticipated festival.

Rudio Fest. June 21st – 23rd. The only festival that celebrates youth-oriented Latin music and culture with internationally headlining acts from all over the Spanish-speaking world. Rudio Fest is an annual multi-day Latin American music festival in Chicago, Illinois held every July on Chicago’s Near West Side. Tickets range from $74.99 – $249.99. For more details including the festival lineup, visit the website here.

Pitchfork Music Festival. July 19th – 21st. The internationally recognized Pitchfork Music Festival presents 40+ acts over the course of three days each summer in Chicago’s Union Park. Highlighting new and classic artists, independently run festival has consistently proven to be one of the most welcoming, comfortable, reasonably priced, and rewarding weekends of music around. Tickets range from $75 – $400. Check out the full lineup by visiting the website here.

Lollapalooza. August 1st – 4th. Music lovers from around the world make their way to Chicago for the annual festival—of the biggest festivals to ever rock the city. With world-class acts, numerous stages, unmatched food experiences, and more Lollapalooza is a major festival that hundreds of thousands attend each and every year. Tickets for the festival range between $130 – $4,200. For the full lineup of acts, visit the website here.

North Coast Festival. August 30th – 31st. The North Coast Festival on brings the electric sounds of House, EDM, Dubstep to Northerly Island. The festival spans over the course of two days during Labor Day weekend. This festival is perfect to close out the end of summer in Chicago. Tickets range between $27- $88. Find the best seat in the house by visiting the website here.

Chicago Jazz Festival. August 23rd – September 1st. The Chicago Jazz Festival showcases the greatest jazz artists from Chicago and around the world. The Chicago Jazz Festival is produced by the Department of Cultural Affairs and Special Events and programmed by the Jazz Institute of Chicago. Get more details on the annual event here.

Riot Fest-photo by Christopher Andrew and George Mucaphy- featured on The Haute Seeker
Riot Fest | Photo by Christopher Andrew and George Mucaphy

Riot Fest. September 13th – 15th. Punk Rock (and more) fills Douglas Park and the city of Chicago during the multi-day music event. In addition, to live music from well known artists—the festival will also feature carnival rides, amazing food vendors, sideshow performers, and more add to the atmosphere of this independent music fest. Tickets are $115 – $1,499.98. To purchase tickets, visit the website here.

World Music Festival Chicago. September 13th – 29th. Enjoy global grooves by award-winning artists from around the world at the city-wide, multi-venue World Music Festival Chicago featuring 50 artists and ensembles representing over 20 countries and regions of the world. For more details, visit the event page here.

Summer Long Festivals

Ravinia Festival. May 11th – Sept 15th. Enjoy a variety of music from hip-hop and jazz, to musicals and more at Ravinia Festival. The suburban venue hosts concerts all summer that are perfect for an evening in the North Shore community of Chicagoland. Check out the full details and participating artists by visiting the website here.

Grant Park Music Festival. June 12- Aug 17. Find the perfect seat as you listen to the sounds of summer. Grab a seat on the lawn, the seating bowl, or for reserve at the 10-week long Grant Park Music Festival. Plan your visit here.

Chicago Summer Dance. June 27-August 24th. Dance to the sounds of 48 different live bands and DJs with steps beforehand at the annual summer event. Free admission. Check out the schedule and choose your favorite night to swing, step, waltz, cha-cha and more.

Movies in the Park-featured on The Haute Seeker-Taylor Justin
Movies in the Park at Millennium Park | Photo by Taylor Justin

Movies in the Park. June 7th – September 9th. Catch a movie under the Chicago skies this summer at Movies in the Park. Movies are brought to the big-screen in neighborhood parks. From classics to major superhero blockbusters. Check out the full lineup by following here. As always, admission is always free.


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