Square Roots festival announces Margo Price, Dehd, and Nick Lowe as headliners

Grammy-nominated artists Margo Price, Dehd, and Nick Lowe are set to headline the Square Roots Festival from July 10 to July 12.

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Caitlin O'Malley

June 10, 2026 · 2 min read

Crowds enjoying a lively outdoor music festival performance under colorful stage lights with a city skyline in the background.

Grammy-nominated artists Margo Price, Dehd, and Nick Lowe are set to headline the Square Roots Festival from July 10 to July 12. This remarkable event asks for no admission fee, inviting everyone into a vibrant urban celebration.

Despite showcasing over 50 music acts, including these notable headliners, and providing extensive amenities, the festival operates on a free-entry model with only a suggested donation. This structure creates an inherent financial tension, challenging traditional festival economics and relying heavily on attendee generosity and local support to sustain its ambitious lineup.

Beyond the Headliners: A Full Festival Experience

More than 50 music acts will perform across multiple stages at the Square Roots Festival, according to Block Club Chicago. Beyond the tunes, attendees can explore various food vendors and local brewers, serving craft beers, vodka cocktails, THC seltzers, and non-alcoholic options. This comprehensive selection transforms the event into a cultural immersion, blurring the lines between a street fair and a music festival.

An Expansive Lineup for Diverse Tastes

The Square Roots Festival's extensive roster includes Margo Price, Dehd, Nick Lowe, Hurray for the Riff Raff, JD McPherson, Robbie Fulks, and Sons of the Silent Age, Block Club Chicago states. Securing multiple Grammy-nominated and critically acclaimed artists while operating on a free model suggests a strong reliance on sponsorship or grants rather than direct attendee revenue for significant talent costs.

Free Entry, Community Support

The Square Roots Festival maintains free admission for all attendees, with a suggested donation of $10 for adults and $5 for seniors and kids, according to Block Club Chicago. This model prioritizes broad accessibility, making high-quality entertainment available without prohibitive ticket prices. It directly challenges the prevailing commercial model, creating a significant financial tightrope that demands robust community backing to bridge the gap between ambition and execution.

Planning Your Visit

The festival's continued success likely hinges on whether attendees embrace the spirit of generosity, proving that high-caliber cultural events can thrive on community support rather than ticket sales.

Your Questions Answered

What types of music are featured at the Square Roots Festival?

The festival showcases a wide array of musical genres, reflecting diverse tastes. While featuring acclaimed artists like Margo Price and Dehd, the event's host, the Old Town School of Folk Music, suggests a strong presence of folk, roots, and Americana styles. This variety ensures entertainment for many musical preferences.

Where is the Square Roots festival held?

The festival takes place on Lincoln Avenue, between Montrose and Wilson streets in Chicago. It is hosted by the Old Town School of Folk Music and the Lincoln Square Ravenswood Chamber of Commerce, according to Block Club Chicago. This location allows for a vibrant street festival atmosphere.

Who organizes the Square Roots festival?

The Old Town School of Folk Music and the Lincoln Square Ravenswood Chamber of Commerce jointly host the Square Roots Festival, as reported by Block Club Chicago. Their collaboration ensures a community-driven event focused on arts and local engagement.