As someone who’s called Illinois home for most of my life, I’ve always been fascinated by how our state has inspired musicians across genres and generations. From the bustling streets of Chicago to the vast cornfields downstate, the Land of Lincoln has a way of seeping into your soul and finding its way into song.
I’ve spent countless nights in smoky blues clubs on the South Side, driven down Route 66 with the windows down, and watched the sun set over the Mississippi River. Each of these experiences has given me a deeper appreciation for the music that captures the essence of Illinois.
In this playlist, I’ll take you on a musical journey through 10 songs that paint a vivid picture of our beloved Prairie State. Whether you’re a lifelong resident or just passing through, these tunes will give you a taste of what makes Illinois so special.
Contents
- 1. “My Kind of Town” by Frank Sinatra
- 2. “Chicago (That Toddlin’ Town)” by Frank Sinatra
- 3. “2120 South Michigan Avenue” by The Rolling Stones
- 4. “65th and Ingleside” by Chance The Rapper
- 5. “Lookin’ Out My Back Door” by Creedence Clearwater Revival
- 6. “Someday We’ll Go All The Way” by Eddie Vedder
- 7. “Chicago” by Sufjan Stevens
- 8. “Homecoming” by Kanye West
- 9. “100 Chicagos” by Lupe Fiasco
- 10. “Johnsburg, Illinois” by Tom Waits
- Submit Your Song to This Playlist
1. “My Kind of Town” by Frank Sinatra
“My Kind of Town” is a classic tune by Frank Sinatra that celebrates the city of Chicago. Written by Sammy Cahn and Jimmy Van Heusen, the song was originally part of the 1964 musical film Robin and the 7 Hoods. It has since become an anthem for the Windy City, capturing its vibrant spirit and iconic landmarks. The lyrics highlight various aspects of Chicago, such as the Wrigley Building and the Union Stockyards, and express Sinatra’s admiration for the city’s unique charm and the warmth of its people. The song’s catchy melody and Sinatra’s smooth vocals have made it a timeless favorite among both residents and visitors of Chicago.
2. “Chicago (That Toddlin’ Town)” by Frank Sinatra
“Chicago (That Toddlin’ Town)” is another classic by Frank Sinatra, originally written by Fred Fisher in 1922. This song paints a lively picture of Chicago, emphasizing its bustling streets, lively atmosphere, and resilient spirit. The lyrics mention State Street, a significant retail corridor in Chicago, and highlight the city’s unique cultural aspects that set it apart from other places, particularly Broadway. The song also references Billy Sunday, a famous evangelist who was unable to curb the city’s vibrant nightlife. Sinatra’s rendition of the song has become one of the most famous versions, celebrating Chicago as a city full of life and energy.
3. “2120 South Michigan Avenue” by The Rolling Stones
“2120 South Michigan Avenue” by The Rolling Stones is an instrumental track that pays homage to Chess Records, located at the titular address in Chicago. Recorded during their 1964 American tour, the song captures the essence of the blues and rock & roll heritage that Chess Records represents. The studio was instrumental in the careers of many legendary artists, including Chuck Berry, Muddy Waters, and Howlin’ Wolf. The Rolling Stones recorded this track at Chess Studios, and it was included on their album 12 x 5. The song serves as a tribute to the significant influence that Chicago’s music scene had on the band and the broader music industry.
4. “65th and Ingleside” by Chance The Rapper
“65th and Ingleside” by Chance The Rapper is a heartfelt tribute to the South Side of Chicago, specifically the neighborhood of Englewood. The song reflects Chance’s personal connection to the area, detailing the challenges and triumphs of growing up there. With soulful beats and introspective lyrics, Chance highlights the community’s spirit and resilience. The song also touches on themes of family, love, and perseverance, making it a poignant and personal ode to his hometown. Englewood’s rich cultural and artistic heritage is also celebrated, showcasing the area’s contribution to Chicago’s vibrant music scene.
5. “Lookin’ Out My Back Door” by Creedence Clearwater Revival
“Lookin’ Out My Back Door” is a song by Creedence Clearwater Revival, featured on their 1970 album Cosmo’s Factory. Written by John Fogerty, the song is known for its whimsical and dream-like lyrics that evoke a sense of nostalgia and childlike wonder. The song begins with a mention of Illinois, setting the scene for a vivid, imaginative journey. Despite some interpretations suggesting drug references, Fogerty has clarified that the song was inspired by the joy of seeing his son play and the whimsical imagery from Dr. Seuss’s book And to Think That I Saw It on Mulberry Street. The upbeat, country rock tune captures the simplicity and beauty of everyday life, making it a timeless favorite.
6. “Someday We’ll Go All The Way” by Eddie Vedder
“Someday We’ll Go All The Way” by Eddie Vedder is a heartfelt tribute to the Chicago Cubs and their long-awaited World Series victory. Released in 2008, the song embodies the spirit and resilience of Cubs fans who endured a 108-year championship drought. Vedder, a lifelong Cubs fan, wrote the song to express hope and dedication, capturing the emotional journey of the team’s supporters. The song gained significant attention when Vedder performed it at Wrigley Field during the Cubs’ World Series celebrations in 2016, symbolizing the fulfillment of a long-held dream for many Chicagoans.
7. “Chicago” by Sufjan Stevens
“Chicago” is one of the standout tracks from Sufjan Stevens’ 2005 album Illinois. The song is an indie folk anthem that explores themes of impermanence and self-discovery. With its repeated phrase “all things go,” the song suggests a sense of transient beauty and the inevitability of change. The lyrics are both personal and universal, reflecting on Stevens’ own experiences and the broader human condition. “Chicago” has been featured in various films and TV shows, further cementing its status as a modern classic. The song’s lush instrumentation and poignant lyrics create a powerful emotional connection, making it a beloved tribute to the city of Chicago.
8. “Homecoming” by Kanye West
“Homecoming” is a heartfelt tribute by Kanye West to his hometown of Chicago, Illinois. Featured on his 2007 album Graduation, the song includes a collaboration with Chris Martin of Coldplay, who provides a memorable chorus. The track uses a metaphorical narrative where Chicago is personified as a childhood sweetheart named “Windy.” Kanye reflects on his relationship with the city, expressing both his love and the regret of leaving it for fame. The song’s lyrics are inspired by Common’s “I Used to Love H.E.R.” and showcase Kanye’s poetic abilities, blending nostalgic melodies with catchy beats. The music video further emphasizes the connection to Chicago, featuring iconic landmarks and local hip-hop acts.
9. “100 Chicagos” by Lupe Fiasco
“100 Chicagos” by Lupe Fiasco is a powerful track that delves into the complex social fabric of Chicago. Released in 2022, the song is part of Lupe’s album Tetsuo & Youth and addresses various social issues, including inequality and violence, that have long plagued the city. Through vivid storytelling and personal reflections, Lupe paints a multifaceted picture of Chicago, celebrating its resilience and cultural richness while also highlighting its struggles. The lyrics are filled with references to different neighborhoods and personal experiences, making it a compelling ode to the city.
10. “Johnsburg, Illinois” by Tom Waits
“Johnsburg, Illinois” is a poignant ballad by Tom Waits, released in 1983 on his album Swordfishtrombones. The song is a tender tribute to Waits’ wife, Kathleen Brennan, who hails from the small town of Johnsburg, Illinois. Through minimalist piano accompaniment and heartfelt lyrics, Waits captures the essence of the town and the deep affection he feels for his wife. The song’s simplicity and emotional depth make it a standout track, evoking the quiet beauty and charm of small-town life in the Midwest.
Submit Your Song to This Playlist
Do you have a track or song you’d like to feature on this playlist? If so, please fill out the form below for our evaluation.
Serena Whitfield is the founder of PlaylistCurator.org. She’s a musician who writes songs for bands. She studied music at the University of Oxford and graduated with distinction. With her expertise, she knows how to review songs and understand what makes good and bad music. Every playlist on our platform is approved by her before publishing to maintain top-notch quality. If you want her to check out your song and maybe get featured on our playlist, submit your song for Serena to evaluate.