Top 18 chicago best songs

Chicago's timeless music has captivated audiences for decades. Their iconic hits, such as "You're the Inspiration", "25 or 6 to 4", and "If You Leave Me Now", showcase the band's signature blend of soaring vocals, intricate harmonies, and infectious rhythms. These songs have become anthems of love, hope, and resilience, cementing Chicago's status as one of the most enduring and influential bands in American music history.

Top 18 chicago best songs
SongAlbumReleaseListens
1. You're the Inspiration Chicago 17 (Expanded & Remastered) 2009 62M+
2. 25 or 6 to 4 Chicago II 2014 31M+
3. If You Leave Me Now Chicago X 2009 18M+
4. Will You Still Love Me? Chicago 18 (Expanded Edition) 2014 16M+
5. Look Away Chicago 19 (Expanded Edition) 2014 15M+
6. I Don't Wanna Live Without Your Love Chicago 19 (Expanded Edition) 2014 7M+
7. Beginnings Chicago Transit Authority 2014 7M+

1. You're the Inspiration - Chicago 17 (Expanded & Remastered)

You're the Inspiration - Chicago

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Song information

ArtistChicagoRelease27-10-2009
Time03:47View62M+
Likes 461K+SuitableN/a
AlbumChicago 17 (Expanded & Remastered)
"You're the Inspiration" by Chicago is a moving ballad that has resonated with listeners for decades. Its heartfelt lyrics and soaring melody evoke a sense of profound love and connection. The song has served as a soundtrack to countless weddings, memorial services, and other deeply emotional moments. Listeners have shared how the song has helped them through difficult times, providing solace and reminding them of the enduring power of love. One listener who lost their spouse said, "This song is very special to me... it seemed like the perfect way to describe how we felt about each other." Another who lost their child wrote, "You never get over losing a child... this song is very special to me."

✨ Read more: 20 Unforgettable Acoustic Songs That Will Resonate With Your Soul

2. 25 or 6 to 4 (2014)

25 or 6 to 4 - Chicago

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Song information

ArtistChicagoRelease12-09-2014
Time07:04View31M+
Likes 204K+SuitableN/a
AlbumChicago II
Have you ever listened to a melody where every note resonates with your heart? "25 or 6 to 4" by Chicago is a song that profoundly evokes such intense emotions. This timeless classic, with its emotive lyrics and unforgettable musical arrangement, has left an enduring impact on listeners for decades. Its passionate performance, particularly Terry Kath's epic guitar solo, showcases the band's extraordinary musicality and undeniable connection to the song's message. Listeners have expressed their admiration for the song's ability to transcend generations, eliciting nostalgia and profound emotional resonance. Its evocative melody and heartfelt lyrics have the power to transport listeners to a realm of pure musical bliss, leaving them deeply moved and profoundly touched.

✨ Read more: 20 Iconic 80s Rock Songs That Will Get You Rocking

3. If You Leave Me Now (Chicago X)

If You Leave Me Now - Chicago

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Song information

ArtistChicagoRelease13-04-2009
Time07:49View18M+
Likes 117K+SuitableN/a
AlbumChicago X
"If You Leave Me Now" by Chicago evokes a profound sense of longing and sorrow. Its gentle melody and poignant lyrics resonate with those who have experienced heartbreak. Listeners often recall the song as a bittersweet reminder of lost love and the passage of time. The song's emotional impact is amplified by its evocative lyrics, which capture the pain of separation and the hope for reconciliation. The acoustic guitar strumming and soft harmonies create an intimate atmosphere, drawing listeners into the raw emotions of the song.

✨ Read more: 20 Best 70s Rock Songs That Will Take You Back to the Golden Era

4. Will You Still Love Me? - Chicago 18 (Expanded Edition)

Will You Still Love Me? - Chicago

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Song information

ArtistChicagoRelease28-02-2014
Time04:19View16M+
Likes 136K+SuitableN/a
AlbumChicago 18 (Expanded Edition)
Whenever the tune of 'Will You Still Love Me?' by Chicago plays, I can't help but reminisce about old memories. That's the power of genuine music. Released in 1986 as part of their album 'Chicago 18,' 'Will You Still Love Me?' encapsulates the essence of timeless romance. With its heartfelt lyrics and Jason Scheff's emotive vocals, the song has resonated with listeners across generations. Its ability to evoke both joy and nostalgia has made it a favorite among hopeless romantics, reminding us of first loves, missed connections, and the bittersweet memories of time passed.

✨ Read more: The 15 1993 best songs

5. Look Away (Chicago - 2014)

Look Away - Chicago

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Song information

ArtistChicagoRelease28-02-2014
Time04:02View15M+
Likes 104K+SuitableN/a
AlbumChicago 19 (Expanded Edition)
"Look Away" by Chicago is more than just a song; it's a time capsule that transports listeners back to the days of their youth. The emotional impact of this power ballad is undeniable, with listeners recalling cherished memories and the profound impact it had on their relationships. The song's timeless appeal lies in its ability to evoke a sense of nostalgia and longing, resonating with those who have experienced both the joy and heartbreak of love. The musical arrangement of "Look Away" is equally captivating, featuring soaring vocals, a driving beat, and intricate harmonies. The lyrics, filled with poignant imagery and heartfelt sentiments, perfectly capture the complexities of human emotions. They speak to the pain of loss, the hope of reconciliation, and the enduring power of love. Whether it's a cherished memory from the past or a reminder of the enduring strength of human connection, "Look Away" continues to touch the hearts of listeners, leaving an indelible mark on their souls.

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6. I Don't Wanna Live Without Your Love (2014)

I Don't Wanna Live Without Your Love - Chicago

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Song information

ArtistChicagoRelease28-02-2014
Time03:59View7M+
Likes 67K+SuitableN/a
AlbumChicago 19 (Expanded Edition)
From the opening notes of "I Don't Wanna Live Without Your Love" by Chicago, listeners are captivated by its heartfelt lyrics and poignant melody. The song's emotional intensity resonates deeply, evoking a longing for love and a fear of being alone. The arrangement is a testament to Chicago's musical prowess, with soaring vocals and a driving rhythm that perfectly complement the song's message. The lyrics paint a vivid picture of a love so strong that life without it is simply unbearable. The singer's desperation is palpable as they plead with their beloved to stay. The song's nostalgic quality transports listeners back to the golden age of Chicago, a time when the band's ballads ruled the airwaves. For many, this song evokes fond memories and a longing for simpler times.

7. Beginnings (Chicago)

Beginnings - Chicago

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Song information

ArtistChicagoRelease12-09-2014
Time06:47View7M+
Likes 43K+SuitableN/a
AlbumChicago Transit Authority
Whenever the tune of 'Beginnings' by Chicago plays, I can't help but reminisce about old memories. That's the power of genuine music. It captures moments in time and evokes emotions that stay with us forever. For many, 'Beginnings' is a song that evokes powerful emotions. It's a song about love, loss, and the bittersweet memories we hold dear. The lyrics are simple yet poignant, and the music is both haunting and uplifting. Whether you're listening to it on the radio, at a concert, or in the privacy of your own home, 'Beginnings' is a song that will stay with you long after the music stops playing.

8. Hard Habit to Break (Chicago)

Hard Habit to Break - Chicago

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Song information

ArtistChicagoRelease16-10-2021
Time04:13View6M+
Likes 43K+SuitableN/a
AlbumChicago 17 (Expanded & Remastered)
While "Hard Habit to Break" by Chicago carries a bittersweet undertone, it's the song's ability to evoke nostalgia and evoke cherished memories that makes it truly captivating. The song's intricate arrangement, featuring two lead singers and the band's signature horn section, creates a rich and layered soundscape that transports listeners back to the vibrant 80s. Whether it's the personal connection to a past love or the appreciation for its musical complexity, "Hard Habit to Break" resonates deeply with listeners. The song's emotional impact is undeniable, as it seamlessly blends elements of longing, regret, and ultimately, a sense of moving forward.

9. Street Player - Chicago 13 (Expanded & Remastered)

Street Player - Chicago

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Song information

ArtistChicagoRelease24-06-2018
Time08:18View5M+
Likes 48K+SuitableN/a
AlbumChicago 13 (Expanded & Remastered)
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10. Colour My World (2014)

Colour My World - Chicago

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Song information

ArtistChicagoRelease12-09-2014
Time06:13View5M+
Likes 41K+SuitableN/a
AlbumChicago II
Released in 1971, "Colour My World" by Chicago is a timeless classic that continues to resonate with listeners. Its soulful lyrics and Terry Kath's exceptional vocals evoke a sense of longing and nostalgia, while the intricate musical arrangement showcases the band's virtuosity. For many, "Colour My World" holds profound emotional significance. It serves as a poignant reminder of cherished memories, such as first dances and enduring love. The song's ability to elicit such deep emotions is a testament to its enduring power and universal appeal, leaving an indelible mark on the hearts of those who hear it.

11. Saturday in the Park - Chicago V (Expanded & Remastered)

Saturday in the Park - Chicago

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Song information

ArtistChicagoRelease04-07-2011
Time03:42View3M+
Likes 19K+SuitableN/a
AlbumChicago V (Expanded & Remastered)
Amidst a musical landscape brimming with electronica, Chicago's "Saturday in the Park" stood apart as a beacon of classic rock, evoking a sense of nostalgia and heartfelt emotion. Its brisk tempo and Kath's soaring guitar riffs captivate listeners, leaving them yearning for what could have been had he not passed away prematurely.

12. I'm a Man (2015)

I'm a Man - Chicago

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Song information

ArtistChicagoRelease06-01-2015
Time07:43View2M+
Likes 27K+SuitableN/a
AlbumChicago Transit Authority
Immerse yourself in the heartfelt anthem 'I'm a Man', where Chicago's evocative lyrics resonate with raw emotions. This poignant ballad captures the essence of human vulnerability, exploring themes of identity, acceptance, and the yearning for recognition. The song's musical arrangement is equally captivating, with its soulful horns and soaring strings creating an unforgettable soundscape. Listeners are drawn to its relatable lyrics and the powerful message of self-empowerment it conveys. "I'm a man, yes I am, and I'm proud," proclaims the chorus, resonating with those who seek validation and a sense of belonging.

13. Make Me Smile (Chicago)

Make Me Smile - Chicago

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Song information

ArtistChicagoRelease17-02-2014
Time07:30View1M+
Likes 12K+SuitableN/a
AlbumChicago II
From the very first notes, "Make Me Smile" captivates with its raw emotional power. Terry Kath's vocals soar with unbridled passion and vulnerability, conveying a depth of feeling that resonates with listeners. The musical arrangement is a masterpiece, blending soaring melodies, intricate harmonies, and an infectious rhythm that propels the song forward. This timeless classic holds a special place in the hearts of Chicago fans. Its poignant lyrics and soaring melody evoke a sense of nostalgia and longing, while the band's dynamic performance delivers an unforgettable musical experience. As one listener remarked, "This song brings tears to my eyes. It was their first big hit, and it remains a timeless treasure."

14. Along Comes a Woman - Chicago 17 (Expanded & Remastered)

Along Comes a Woman - Chicago

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Song information

ArtistChicagoRelease04-11-2021
Time04:30View899K+
Likes 9K+SuitableN/a
AlbumChicago 17 (Expanded & Remastered)
Despite its upbeat tempo and infectious rhythm, "Along Comes a Woman" by Chicago carries a bittersweet undertone that resonates deeply with listeners. The song's evocative lyrics evoke a sense of nostalgia and longing, capturing the bittersweet emotions of a bygone era. The intricate musical arrangement, featuring soaring horns and Peter Cetera's signature vocals, creates a captivating soundscape that perfectly complements the song's emotional core. As listeners reminisce about the carefree days of the 1980s, "Along Comes a Woman" serves as a poignant reminder of youthful innocence and the bittersweet passage of time. Its enduring appeal lies in its ability to transport listeners back to a simpler time, evoking a mix of joy and longing that lingers long after the final note has faded away.

15. Happy Man - Chicago VII (Expanded & Remastered)

Happy Man - Chicago

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Song information

ArtistChicagoRelease06-10-2012
Time04:25View744K+
Likes 6K+SuitableN/a
AlbumChicago VII (Expanded & Remastered)
Released in 1988, "Happy Man" by Chicago is an enduring classic that showcases the band's signature blend of soaring vocals and intricate harmonies. Pete Cetera's lead performance is nothing short of captivating, infusing the song with a palpable sense of joy and yearning. The lyrics, a testament to the transformative power of love, resonate deeply with listeners, many of whom cite it as one of their all-time favorites from the band. The song's musical arrangement is equally impressive, featuring a lush orchestration that complements the soaring vocals. The result is a timeless ballad that has stood the test of time, leaving an lasting impression on listeners with its emotional resonance and musical sophistication.

16. Old Days (Chicago)

Old Days - Chicago

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Song information

ArtistChicagoRelease05-01-2014
Time03:30View459K+
Likes 3K+SuitableN/a
AlbumThe Nashville Sessions
In the midst of a musical landscape defined by lively electronic beats, "Old Days" by Chicago stands apart, offering a poignant and nostalgic journey back in time. Its poignant lyrics and masterful arrangement evoke a bittersweet symphony of memories, stirring emotions that resonate deeply with listeners. The song's nostalgic aura transports listeners to a bygone era, evoking a profound sense of longing and appreciation for the past. Its emotional impact is amplified by its captivating melody and heartfelt lyrics, which paint a vivid picture of friendships, adventures, and the bittersweet passage of time. "Old Days" serves as a timeless anthem, reminding us to cherish the moments that shape our lives and to find solace in the memories that connect us to our past.

17. Baby, What a Big Surprise (2012)

Baby, What a Big Surprise - Chicago

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Song information

ArtistChicagoRelease10-10-2012
Time03:32View186K+
Likes 2K+SuitableN/a
AlbumChicago XI
Have you ever listened to a melody where every note resonates with your heart? "Baby, What a Big Surprise" by Chicago is exactly that kind of song. Released in 1982, this timeless classic has captured the hearts of music lovers for generations. With its emotional lyrics and soaring melodies, "Baby, What a Big Surprise" evokes a sense of nostalgia and longing. The song's intricate musical arrangement, featuring lush harmonies and a driving rhythm, perfectly complements Peter Cetera's soulful vocals. Whether you're a lifelong fan of Chicago or simply appreciate great music, this song is sure to leave an unforgettable impression.

18. Song for You

Song for You - Chicago

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Song information

ArtistChicagoRelease25-10-2018
Time03:41View126K+
Likes 827+SuitableN/a
AlbumChicago XIV (Expanded & Remastered)
If you're a fan of Chicago's earlier hits like "If You Leave Me Now" and "Hard Habit to Break," then you'll appreciate the emotional depth and musical maturity showcased in "Song for You" This heartfelt ballad showcases the band's signature soaring harmonies, backed by a gentle acoustic guitar and subtle strings. Listeners have praised "Song for You" for its ability to evoke a sense of nostalgia and longing. The lyrics, which express feelings of love and loss, resonate with listeners on a deep level. The song's simple yet effective arrangement allows the vocals and lyrics to take center stage, creating a truly moving and memorable experience.