Arts & Entertainment

10 Street Fests to Explore Through September

Emily Rosca | The Phoenix

Summer might be slowly coming to an end, but street festivals aren’t. Every weekend, a different neighborhood hosts a street festival. From food fests, art shows and music festivals, there’s no shortage of events to attend each weekend. 

Attending street fests is a great way for first-year students to experience everything Chicago has to offer, from otherworldly cuisine to diverse culture. The Phoenix has compiled a list of best street fests to attend through the end of September. 

Logan Square Food Truck Social 

The Logan Square Food Truck Social is rolling into Logan Square for its third annual event Aug. 24-26. The social will host an array of food trucks and restaurants, including Beaver’s Coffee & Donuts, Cheesie’s Pub and Grill, Dia de Los Tamales and 5411 Empanadas, among others. 

Programmed by Chicago’s Empty Bottle Presents, the Logan Square Food Truck Social will showcase local and national music artists performing a variety of music throughout the three days. 

The grounds will have two stages set up — a main stage and DJ stage. Artists including Palm, Quarter Mile Thunder and The Family Gold will perform at the main stage, while Prince Paul, Ayana Contreras and DJ Oreo have sets at the DJ stage. 

Sampler tickets are $20. A sampler ticket consists of six individual tickets which allows fest-goers to try six sample-sized portions from the participating food trucks. There is an optional $5 donation at the gate, with proceeds benefiting local organizations. 

The Logan Square Food Truck Social is located on Humboldt Boulevard between Armitage Avenue and 606 Trail. 

Chicago Jazz Festival 

Programmed by the Jazz Institute of Chicago, the Chicago Jazz Festival celebrates jazz with free concerts throughout the city Aug. 24-Sept. 2. 

The Chicago Jazz Festival celebrates its 40th anniversary by showcasing dozens of artists, from national and international performers to legendary musicians and modern newcomers, including Black Diamond, Chris Speed Trio, Kurt Elling, Diane Reeves and Ramsey Lewis.

The festival is held at venues throughout the city, including neighborhood locales such as the Edgewater Beach Apartments in Edgewater and The Green Mill in Uptown. The main event, beginning Aug. 30, will be held at the Chicago Cultural Center and Millennium Park. 

Randolph Street Market 

As college students begin heading back to school, Randolph Street Market continues its summer season with the “Back to Cool” event Aug. 25-26. 

Randolph Street Market is considered to be one of America’s largest urban antique markets, and attendees can find unexpected, unique items including art, vintage clothing, jewelry, vinyl records and home decor. Stationed throughout the market grounds are market bars, cabana and shade areas and a live music line-up. 

For those unable to attend this weekend’s event have several more opportunities to visit. The Randolph Street Market summer season continues hosting events once a month through December.

The Randolph Street Market is located at 1341 W. Randolph St. from 10 a.m. to 5 p.m. Tickets can be purchased online at the fest’s website. Entrance to the market costs $15. Students can purchase tickets for $5 or buy two and get one free with a valid student ID. 

Taste of Polonia

Taste of Polonia is back for its annual festival on Labor Day weekend, Aug. 31-Sept. 3. Fest-goers will be able to sample dishes from restaurants across the city and indulge in the many flavors of Poland. 

Among the foods featured on the menu at this year’s festival are pierogi, turkey legs, Polish pizza, cabbage and noodles. Participating establishments include Tata’s Pierogi, Babuschka Polish Foods and Home Bakery and Dumpling House. 

Aside from the varieties of traditional polish dishes and beers, Taste of Polonia will have tasting and cooking classes, carnival rides and live music. Spanning across four stages, more than 30 bands will perform a wide range of genres from polka and rock to jazz and classical. 

Taste of Polonia is held at the Copernicus Center (5216 W. Lawrence Ave.). Tickets can be purchased on-site or online at Tickets cost $5 before 5 p.m. and $10 afterward. 

Donut Fest at the Zoo 

Spend the day tasting some of Chicago’s best donuts while sipping on mimosas, beer or coffee at Lincoln Park Zoo. Guests can stroll around Chicago’s only free zoo and visit the animal exhibits. 

Admission to the event gives guests exclusive access to animal exhibits, where fest-goers can attend a lecture about polar bears at the Walter Family Arctic Tundra and an African Penguin feeding at the Robert and Mayari Pritzker Penguin Cove.

Tickets to Donut Fest at the Zoo cost $22.85 and can be purchased online.

Chicago Bourbon and Barbecue Fest 

Southern hospitality and Midwestern charm converge for the second annual Chicago Bourbon and Barbecue Fest Sept. 8-9 in Roscoe Village. 

Taking the spotlight at this festival are smoked meats, from chicken to ribs, and bourbon whiskeys from distilleries in Chicago and across the country. Barbecue vendors set to serve at the festival include Austin’s Texas Lightning BBQ, Blowin’ Smoque BBQ, Main Street Grill and Tandoor Char House. 

To supplement the assortment of meats and bourbons present at the festival will be soulful bands The Congregation, Lynne Jordan & The Shivers and T.L. Williams, among others.  

The Chicago Bourbon and Barbecue Fest is located at 2000 W. Belmont Ave. Bourbon tasting tickets cost $35 for 12 sampling tickets. 

Lakeview East Festival of the Arts 

Celebrating 14 years in Lakeview, the Lakeview East Festival of the Arts showcases the works of more than 150 artists ranging from painters and sculptors to jewelry and furniture makers. 

Accompanying the artist exhibits will be music performances spread across the main and garden stages. Up-and-coming artists and cover bands including Big Suit, American Grizzly, Sixteen Candles and Spare Parts will be playing sets throughout the festival’s two days. 

The Lakeview East Festival of the Arts is located on Broadway Boulevard from Belmont Avenue to Hawthorne Place. Admission into the festival is free. 

Sam Adams’ Lakeview Taco Fest

Few activities are more enjoyable than an afternoon spent devouring tacos. In honor of this all-time favorite dish, Lakeview hosts the sixth annual taco fest Sept. 15-16. Celebrating the start of fall, this taco fest will feature seasonal beers to complement the variety of imaginative tacos. 

Among the present vendors will be Flaco’s Tacos, Beat Kitchen, Frontier and Taco Joint. Participating taquerias will serve tacos made from an assortment of ingredients — from traditional chicken, steak, chorizo and beef tacos to creative fillings such as seafood, goat and duck — meant to please any and all cravings.

After indulging in a variety of tasty tacos, fest-goers have the opportunity to vote for Chicago’s “Best Taco.” Café Tola, Dona Tola and D.S. Tequila were voted first, second and third-place winners, respectively, at the 2017 Lakeview Taco Fest. 

Accompanying the flavorful tacos will be live music entertainment and lucha libre Mexican wrestling, a traditional form of wrestling. 

Sam Adams’ Lakeview Taco Fest is located on Southport Avenue between Addison and Roscoe Streets. A $10 donation is suggested before entering, with proceeds benefiting local organizations Friends of Lakeview and the Lakeview Chamber of Commerce. 

West Loop Art Fest

After a successful first two years, the West Loop Art Fest returns for its third year of art shows and entertainment Sept. 16-17. More than 120 artists from across the country will showcase their artwork in Chicago’s dynamic and ever-evolving West Loop. The two-day art fest will feature four blocks of art showcases, artist demonstrations and food trucks. Fire dancers and hot glass blowers are also scheduled to make appearances. 

Amid the artists will be live music performances from an array of musicians, including David Montoya, Rae Chardonnay and Chicago’s DJ Lady D. 

The West Loop Art Fest is located on Fulton Street from Morgan Street to Racine Avenue.


In celebration of fall and German heritage, the 17th annual Oktoberfest is returning to Chicago Sept. 28-30. What originally began as an event in a parking lot has transformed into a full-fledged three day festival filled with beer, brats and bands. 

At the Craft Beer Night, which occurs Sept. 28 and 29 from 6 p.m. to 9 p.m., fest-goers can sample more than 40 craft beers, including lagers, pale ales and sweet malt beers, for $50. Included in the cost is a souvenir pretzel, a pretzel necklace and admission into the festival. 

Sixteen Candles, Polkaholics and American English are among the groups set to entertain.

Oktoberfest takes place at in West Lakeview at St. Alphonsus Church (1429 W. Wellington Ave.). Craft Beer Night will be held in the German beer hall within St. Alphonsus. 

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