A Guide to Chicago Street Festivals for 2019

When the weather in Chicago finally starts to turn warm, you can count on a different street festival taking place every single weekend. You probably know about the bigger ones, but we wanted to highlight the street festivals that are their neighborhood's pride and joy.

Beyond the typical draw of festivals—being able to enjoy booze, food truck fare, and local bands—these festivals show off their neighborhood's culture and heritage, doubling as an opportunity to have fun while exploring a new part of Chicago.

From now until September, in all corners of the city, here are the festivals that anchor their neighborhood.

May 31 - June 2: Do Division

Courtesy of Do Division Street Fest

Harkening back to Wicker Park’s early days as a rock mecca, a $10 donation is all it costs to see bands like Russian Circles, The Skatalites, and Meat Puppets at the Do Division Street Fest on Division Street between Damen and Leavitt. You’ll also find family activities and fashion shows featuring local designers. 

June 1-2: 57th Street Art Fair

57th Street Art Fair
57th Street Art Fair / Photo by 393edge / CC BY

Hyde Park is home to the Midwest’s oldest juried arts fair. The festival’s free admission frees up more funds to score paintings, sculptures, and jewelry by local artists.

June 1-2: Hyde Park Brew Fest

Photo courtesy of Hyde Park Brew Fest

Located in the heart of its eponymous neighborhood, Hyde Park Brew Fest includes city favorites like Revolution Brewing and global superstars like Sam Adams Brewing. This festival combines the best of the beer-making world with local musical acts. The event is held at 53rd and Harper, admission is free and tickets for beer sampling start at $25.

June 7-9: Midsommarfest

Photo courtesy of City of Chicago

Andersonville celebrates its Swedish heritage with a smorgasbord of food, music, and shopping down the neighborhood's main thoroughfare, Clark Street. The Swedish Stage features an ABBA tribute band, and a $10 donation at the festival gates supports neighborhood programming.

June 8-9: Pilsen Food Truck Social

Photo courtesy of Chicago Tribune/Printers Row Lit Fest

You can either pay the $5 donation to get into the food truck festival, or opt for a $20 “sampler ticket” that gets you six sample-sized portions from participating food trucks and restaurant vendors. Food trucks roll in from all around the city, and vendors include Pilsen favorites like Dusek’s and Honky Tonk BBQ.

June 8-9: Printers Row Lit Fest

Photo courtesy of Chicago Tribune/Printers Row Lit Fest

The highlight of the summer for the city's bibliophiles, Printers Row Lit Fest pays homage to the neighborhood's literary history with two days of booksellers, author panels, and local publishers. Most events are free but some can run up to $35. The fest is from June 8-9 and will be located throughout the Printers Row neighborhood.

June 13-16: Puerto Rican Festival and Parade

Photo courtesy of The Puerto Rican Agenda

A neighborhood parade is the culmination of Humboldt Park's celebration of Caribbean culture. This year, the festival will feature an area to watch Puerto Rican films, visiting authors, a cultural fair, and a blood drive. The parade kicks off at 2 p.m. on Saturday, June 15th.

June 22-23: Chicago Pride Fest

Photo courtesy of nathanmac87

Regarded as one of the city's most boisterous festivals, Chicago Pride Fest takes over the Boystown neighborhood for two days of dancing, drinking, and pride. Admission is a $10 suggested donation, and the fest will be held on Halsted Street from Addison to Grace Street. The Pride Parade is held the weekend after (Sunday, June 30) at noon.

June 28-30: Logan Square Arts Festival

Photo courtesy of Logan Square Arts Festival

Well-known bands Hop Along, Speedy Ortiz, and The Beths are headlining this year at the Logan Square Arts Festival that takes place around the neighborhood’s landmark monument. Admission is a $5 suggested donation.

June 22-23: Ravenswood On Tap

Photo courtesy of Malt Row Chicago

Entering its third year, Ravenswood on Tap joins the ranks of Chicago street festivals celebrating the city's favorite summer pastime—drinking outdoors. The event is held on Ravenswood and Bertreau Avenues. For just a $5 donation, you can have access to the neighborhood's surging number of local breweries.

July 13: FIGMENT Chicago

Photo courtesy of Figment Project

Originally a one-day event on Governors Island in New York, this festival has since moved to Chicago's Logan Square neighborhood. Billed as a festival where "anyone can be an artist," participants can play, dance, and paint at the festival's interactive areas. FIGMENT is free and will be held in Logan Square's Mozart (Amadeus) Park.

July 12-14: Irish American Heritage Festival

Photo courtesy of Irish Heritage

A three-day festival that celebrates the city's unapologetic devotion to all things Irish, this event includes traditional Irish music, food, drink, and dozens of vendors. The festival is held July 12-14 on the grounds of the sprawling Irish American Heritage Center, located in Irving Park. Tickets purchased in advance are $10.

July 5-7: West Fest

Photo courtesy of West Fest Chicago

Since debuting in 2004, West Fest has established itself as one of the city's most dynamic festivals. Featuring acts like Los Campesinos! and John Maus, West Fest focuses on supporting local vendors and restaurants. The festival also hosts Pet Fest and Kid Fest, providing festival fun for the entire family. The event will be held July 5-7 in West Town on Chicago Avenue between Damen Avenue and Wood Street.

July 20: Chalk Howard Street Festival

Photo courtesy of The Silverman Group 

On July 20, Howard Street in Rogers Park will become a canvas for internationally renowned 3D street artists and local 2D chalk artists. Come for the mind-blowing artwork, but stay for the live music, global cuisine, drinks, and the vibrant personality of Howard Street. This family-friendly festival is free, so everyone can enjoy this one-of-a-kind Chicago art experience.

July 21: Chinatown Summer Fair

Photo courtesy of City of Chicago

Entering their fourth decade in the city, Chinatown Summer Fair takes place in its eponymous neighborhood and features dance processions, artisans, and the neighborhood's classic cuisine. Live bands, martial arts displays, and Taiko drums will also be a part of this iconic celebration. This free event will be held July 21 in Chinatown.

July 19-21: Taste of River North

Photo courtesy of City of Chicago

Located in Ward Park, this festival offers up the best of River North's culinary scene, attracting over 50,000 people. In between beers and meals, enjoy the live music and family-friendly activities.

July 19-21: Colombian Fest Chicago

Photo courtesy of Columbian Fest Chicago

The El Gran Festival Colombiano (a.k.a. Colombian Fest) in Hermosa is the biggest two-day celebration of Colombian culture in the city. Everything comes with an authentic flair, from the live music to the carnival rides to the cuisine. Kelvyn Park will be the epicenter of Colombian culture for the weekend.

July 25-28: Fiesta Del Sol

Photo courtesy of Fiesta Del Soul

What started out as a block party to celebrate Pilsen, Fiesta Del Sol is now one of the largest festivals in the Midwest, drawing over a million people. They come for the live entertainment, local art, food, carnival rides, sporting events, and more. All revenue goes back to the Pilsen community.

July 27-28: Taste of Lincoln Avenue

Food on a grill
Taste of Lincoln Ave features food, venders and musical acts. / Photo by reverent / CC0

Sprawling across several blocks of Lincoln Park, this festival features more than 250 vendors, lots of food, and over 30 musical acts on four stages. All the money raised goes to fund grants for local charities, schools, parks, and neighborhood improvements. Since it began the festival has raised over $2.2 million for the community.

July 26-28: Wicker Park Fest

Photo courtesy of Kumar McMillan / CC BY-SA

Wicker Park Fest is all about recognizing its neighborhood's rich musical heritage, vibrant nightlife, and popular restaurants. Local food vendors, arts and crafts booths, three stages of music, and dozens of retail vendors line the streets during this two-day party.

August 2-4: Jeff Fest

Photo courtesy of City of Chicago

Colloquially known as Jeff Fest, this northwest side neighborhood party in Jefferson Park isn't one of the biggest in Chicago, but its intimate setting makes it an ideal spot for enjoying live music from local bands as well as touring acts. There's also sure to be kids' activities, artisans, and plenty of vendors.

August 3-4: Edge Fest

Photo courtesy of City of Chicago

Celebrating all things Edgewater, Edge Fest will be full of local musicians and vendors surrounding an outdoor cafe setting. Expect to dance, eat, play, and shop all day.

August 10-11: Northalsted Market Day

Market Days
Northalsted Market Days / Photo by Alan Light / CC BY

Claiming to be the largest street festival in the Midwest, this LGBTQ-centric, two-day event takes over Lakeview—particularly the Boystown and Wrigleyville areas—with food, booze, arts and crafts, and entertainment (performers this year include Daya and Icona Pop). A $10 donation benefits the Northalsted Business Alliance and The Legacy Project.

August 16-18: Edison Park Fest

Photo courtesy of Edison Park Chamber of Commerce

Edison Park's longtime festival features a beer garden, a craft fair, and local bands performing each night. A $5 suggested donation and festival proceeds benefit neighborhood improvement programs.

August 23 - September 1: Chicago Jazz Festival

Jazz Fest
Chicago Jazz Festival / Photo by Zepfanman.com / CC BY

A Labor Day Weekend tradition since 1979, The Chicago Jazz Festival takes place in Millennium Park at the Chicago Cultural Center. Showcasing both national and international talent, the 10-day celebration will also feature an art fair as part of the festivities. Admission is free.

August 16-18: Glenwood Avenue Arts Festival

Photo courtesy of Glenwood Ave Arts District

An arts market with more than 100 artists, open studios, and live entertainment takes over Rogers Park during this annual weekend-long festival. The Friday Night Cobblestone Jam event kicks off the free festival.

August 24-25: Ukrainian Days Festival

Photo courtesy of selfrelianceUAFCU

Held during Independence Day of Ukraine, Ukrainian Village hosts its annual festival featuring food, live music, and dance performances. Donations are requested at the entrance.

August 23-25: Taste of Greektown

Photo courtesy of Thomas Sly / CC BY

Food is the focus of Greektown's free fest, where many of the neighborhood's restaurants set up shop on Halsted Street. Greek bands and games promise to also get you in the "opa!" spirit.

August 24-25: Bucktown Arts Festival

Photo courtesy of Bucktown Arts Fest

Priding itself on being “free of the corporate stuff,” this Bucktown festival is a sprawling art sale with live music, a craft beer tent, and food trucks. Admission is free, and proceeds benefit neighborhood arts programs.

September 6-8: Little Village Fest

Photo courtesy of City of Chicago

Celebrate Mexico's Independence Day in Little Village. On Sunday of this weekend-long event, the festival is the end location of the 26th Street Mexican Independence Day Parade. Before that, the fest offers food, music, arts and crafts, and carnival rides. Admission is free.

August 30 - September 2: Taste of Polonia Festival

Photo courtesy of Taste of Polonia

Located in Jefferson Park, the Taste of Polonia Festival highlights Polish culture and features an assortment of Polish foods and beers. Offering live music, cooking classes, and carnival rides, Taste of Polonia is a community event the whole family can enjoy. Prices are $5 before 3 p.m. and $10 after 3 p.m. Kids 12 and under get in free.

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