Enjoy free, live music on select Tuesday evenings throughout the summer in the green space of Gallagher Way.
MAY 20 - SEPTEMBER 30
Old Town School Happy Hours return this summer to Gallagher Way! Join us for a weekly live music experience sure to end your day on a high note. From the familiar sounds of pop, rock, and folk to unique melodies from around the world, many Happy Hours will also feature free dance lessons or other interactive music experiences. Suitable for all ages, so bring your families and friends!
Also, don't miss Wiggleworms at Gallagher Way on Tuesday mornings!
More information on events at Gallagher Way
Tuesday, May 20th from 5-7pm
Shoji Naito and the Chicago Blue Aces - Blues
Chicago Blue Aces is led by Blues Guitarist Shoji Naito, a long-time member of the legendary Eddy Clearwater Band. Shoji's album "New Cool Old School" was nominated for the 2016 Blues Blast Music Award. The band features soulful Kirk Manley on vocals and harmonica and marvelous Lee Kanehira on keyboard and vocals. Drummer Steve Bass and Bassist John Lauler will keep the tightest groove for the whole show.
Tuesday, June 3rd from 5-7pm
Dill Costa Quartet - Brazilian Jazz
One of Chicago's best-kept secrets, Dill Costa is a multi-talented Brazilian performer. She is a singer, composer, actress and Brazilian dance instructor. Raised in Rio de Janeiro, Dill is a performer who represents authentic Carnaval music, which is a part of Brazil's rich musical legacy. On the stage, Dill starred in several major Brazilian productions of American Musicals. In Brazil, she also had opportunities to sing with Eduardo Dusek, Oswaldo Montenegro, Marcos Lima and Joao Pinheiro. Since relocating to Chicago in 2003, Dill has dedicated herself to music and can be seen regularly singing with A Cor do Brazil since 2004 (Luiz Ewerling Group), Marshal Vente Tropical Jazz Band since 2008, Bossa Tres Band since 2005, and Dill Costa Quartet, her personal project, playing her original songs.
Tuesday, June 24th from 5-7pm
Windy City Ramblers - Brass / Second Line
The Chicago Windy City Ramblers INC is a non-profit brass band organization that is dedicated to the cultural development of the youth of Chicago through the Brass Band and Second Line culture. The Windy City Ramblers Brass Band builds from the musical legacy and festive spirit of the New Orleans Brass Band and Second Line culture while embracing the rich creative history of Chicago music culture and musicianship.
Tuesday, July 8th from 5-7pm
Jacob Sweet & The Western Harmony - Country meets Classic Soul
A fixture of the Chicago music scene for many years, Jacob Sweet has performed thousands of shows all over the U.S and abroad. He has been featured on dozens of recordings and shared the bill with many well known names in the country and rock world. His band, the Western Harmony, mixes Country and Americana with Classic Soul to make an uplifting and joyful sound for people of all ages and walks of life.
Tuesday, July 15th from 5-7pm
Cicada Summer - High-Energy Acoustic Folk
In the heart of Chicago, there's a band playing the songs of summer all year round, and like their namesake this little band makes a big sound. Inspired by bluegrass, Irish and folk music traditions, CICADA SUMMER brews up a warm acoustic blend of tunes spiced with a pinch of city flair. Their energetic sets feature sunny vocal harmonies, folksy favorites, scattered fiddle tunes, golden oldies, and even the occasional pop-hit gone acoustic. Tap your toes and hum along to some strings on wings!
Tuesday, July 29th from 5-7pm
Moya Cultural Arts - West African
Moya Cultural Arts is a grassroots organization, dedicated to promoting peace, culture and education, through African Diasporic Drum and Dance. Enjoy traditional rhythmic sounds of West Africa and the Caribbean. Be blown away by dynamic dancers and energetic movements of the Diaspora. Join in on the fun, grab an instrument and be a part of our drum circle or even learn a few steps!
Tuesday, August 12th from 5-7pm
Walkin' on Sunshine - Upbeat Soulful Rock
Walkin' on Sunshine has been called Chicago's Wrecking Crew, after the legendary collective of LA musicians in the 60's. These 4 musicians have played on countless albums by Chicago musicians and can be found in the local clubs in dozens of bands every week of the year. Together they play songs by Steve Dawson and Gerald Dowd along with Rock, Soul, R&B and Country gems.
Tuesday, September 9th from 5-7pm
Disaster Kid - Nostalgia Indie Rock
Packed with careful reflection and passionate melodies, "nostalgia" rock band Disaster Kid is keen to write a song that remembers: a gas station stop between two states, a curious scene outside a local dive, a solemn exchange in a zoo's reptile house. Their new EP Rare Bird (March 2025) is a collection of those notices and observations, attempting to digest the present moment in an attention-demanding world and pinpointing the small details that strike us in large ways. Disaster Kid formed piece by piece in Chicago, each member a transplant hailing from different states. They now all claim home to the city, embedded in its rich and vibrant community of music.
Tuesday, September 30th from 5-7pm
Lisa DeRosia & Lush Budgett - Folk/Rock/Americana
Lisa DeRosia and Lush Budgett prove equally at home on contemporary pop, country swing, vintage country, and all points between, including a smoky gypsy groove thrown in for good measure. The band features songwriter and vocalist Lisa DeRosia with Greg Schultz on Guitar and Pedal Steel, Steve Doyle on Guitar, and Gerald Down on Drums. "Hushed, rustic and rooted firmly in the Midwest tradition, country-tinged love songs fueled by Lisa DeRosia's unique vocals and Greg Schultz's impressive guitar and pedal steel work... solid songwriting, tasteful arrangements, strong musicianship." - Chicago Tribune.
