Our final stop on our Summer in the Cities tour is Chicago, where lakefront winds, crowded L tracks and glowing dive bars color the music echoing from basements, rehearsal halls and neighborhood clubs. Don and Dude drop the needle on two Chicago born records that traced how the city’s grit, pride and restless motion pressed into soul and horn heavy rock, turning street level stories and late night jams into full album statements.
The Albums
Curtis Mayfield – Super Fly (1972)
Curtis Mayfield used his Chicago roots and Curtom studio band to craft a tight, cinematic soul and funk set about poverty, drugs and survival, following dealers, hustlers and their victims with smooth grooves, sharp bass lines, orchestral strings and clear eyed lyrics that challenged the blaxploitation film it accompanied. Across love songs, instrumentals and story tracks, he stitched together one flowing portrait of inner city life that felt as much like social commentary as soundtrack.
Chicago – Chicago Transit Authority (1969)
Chicago’s double length debut captured a seven piece Chicago band fusing blues, jazz and rock with a full horn section, letting Terry Kath’s guitar, Robert Lamm’s songs and James Pankow’s arrangements drive long jams, protest audio and hooky tunes that showed how a loud city rock group with brass could sound before the ballads and soft rock era. The record played like a full tour of late 60s Chicago energy, from club tested covers to politically charged suites tied to the 1968 convention.
Diggin Albums
Jack White – Frozen Charlotte (2026)
Jack White leans into raw, distorted blues rock riffs and theatrical energy on Frozen Charlotte, pushing his solo sound toward louder, more aggressive guitar workouts.
Urge Overkill – Rock and Roll Submarine (2011)
Urge Overkill returned with crunchy guitars, swagger and melodic hooks on Rock and Roll Submarine, reconnecting their Chicago alt rock grit with a more reflective comeback tone.
When in Rome – Illuminations (2026)
When in Rome updates their classic 80s synth pop textures on Illuminations, adding more adult, reflective lyrics over glossy keys and programmed beats.
Madonna – Confessions II (2026)
Madonna revisits continuous club style mixes on Confessions II, teaming with Stuart Price and guests like Sabrina Carpenter and Feid to blend nostalgic dance sounds with stories from her early New York days and present life.
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“I’m impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work.” – Michael Douglas
