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Top 50 Best Chicago Songs of All Time

In 1970, I was at the Isle of Wight Festival. I hoped to see Miles Davis and find out what all the fuss was about. I was also looking forward to seeing Joan Baez and Joni Mitchell. And, at the louder end, Jethro Tull, Jimi Hendrix, Taste with Rory Gallagher, Free, and The Who.

An unknown band came on… 

They were introduced as the Chicago Transit Authority. Cue polite applause. I had always liked Blood Sweat and Tears, so when I saw the horns, I thought, okay, let’s see. 

For the first hour, they were okay. A bit like a watered-down BST, without the serious jazz influences. I didn’t realize many years later that I would be writing about the best Chicago songs of all time.

But then they got to the end of their set, and the last two songs changed most people’s minds. They did “25 or 6 to 4” and finished with a version of Spencer Davis’ “I’m A Man.” It turned a good performance into a great one. Chicago had arrived in the UK.

The Beginning

They were formed in Chicago and, after a name change, became the Chicago Transit Authority. They could be described as a rock band, but at the Isle of Wight, they seemed a little bit more than that. The horns added power, the experimentation obvious, and the guitar player was very good.

Over the years, they changed quite a bit; some would say not for the better. We seemed to go very quickly from the powerhouse that was “I’m A Man” and “25 or 6 to 4” to gentle ballads.

A Change

I am not sure why that happened. But some of those ballads were excellent Chicago songs, so maybe they just found their niche.

Despite the accident when guitarist Terry Kath shot himself in the head and other numerous changes, they are still going today. And they still pack out venues. Choosing the best songs by Chicago is going to take us back a long time. 

Very Politically Minded

They often made references to the evil inherent in the “military-industrial complex” and air pollution. They also talk about America’s “most famous crook,” Republican president Richard Nixon. We shall look at one of those songs a bit later.

Plenty then to look at and consider. Maybe we should start at the very beginning, but we will leave the Isle of Wight till last.

Top 50 Best Chicago Songs of All Time

1 Question 67 And 68

This was a song from their first album entitled Chicago Transit Authority from 1969. Released as what they thought was an ideal choice for a single, it bombed. If it hadn’t been for people who bought the album for other songs like “I’m A Man,” I doubt we would have heard of this song again.

That would have been a bit of a shame because, in my view, it is one of Chicago’s best songs. Listening to it now, the horn arrangements sound a bit dated. Maybe we should expect that. But, the vocals still sound good, and the piano parts are very well played.

A Strange Title?

Seemed at the time to be a little like the sort of title Bob Dylan might give a song. And the song was structured in a very ‘Dylan-esque’ way in that the title is not even sung until the very end.

The beginning is very much BST, except for Terry Kath’s flying guitar under it. The middle, with its tempo change, is also interesting. 

Never a single, especially in 1969, so I don’t know what the powers that be were thinking of. But, an excellent track that demonstrated to those of us that heard it that there was plenty more to come yet.

2 Does Anybody Really Know What Time It Is?

From the same album and one of the tracks that some people bought it to hear. It was written and sung by the band’s keyboard player Robert Lamm. When you heard this for the first time, you began to think that this group was going to be a big noise in the jazz/rock movement.

In some ways, they were. But, to me, this is Chicago being more technical in their performance than, shall we say, “I’m A Man.” A good song, again with a very Blood Sweat and Tears beginning, with plenty of horns and experimental patterns, and timings. 

When the song starts, you can hear that they had written a good ‘semi-ballad.’ It wasn’t much of a step from this to some of the other later ballads that brought them huge success.

All Together Now

It is said that this was the first track they ever recorded, and they were all playing live together. That is probably why it is not sterile and slightly flat like some recordings you hear. In this, there is plenty of life and atmosphere. Great track, and it sold well, reaching #7 in the US and Canada.

3 You’re the Inspiration

This is from Chicago’s fourteenth studio album released in 1984, titled Chicago 17. In researching these articles for the “Best songs by…” you get to read a range of opinions. This song has its fair share.

I happen to think it’s a good song, and I suppose you could say it was Chicago’s attempt at a “power ballad.” The 80s definition of a power ballad is plenty of emotion in the vocal, some big chords, and a powerful chorus.

Moving On

However, whilst it is a good song, they have now moved on from those early days. They are not going to be Blood Sweat and Tears 2.0, and it sounds like they don’t want to. If that is what they want, that is fine.

Someone wrote, “It’s too sweet and sugary.” I can understand that they seemed to have embarked on a different path for their singles and their public profile. But, let’s not overlook the fact. Sugary and too sweet aside, it is one of the most popular Chicago songs.

4 Saturday in the Park

Released in 1972 on the album Chicago V, this became their most successful single to date at the time. In some ways, it had a limited release, only being available in America, Canada, and Australia. It reached #3 in the former.

It is a laid-back pop/jazzy song, which is where their musical style was moving. I have included it here not because of its musical contribution to their catalog. It is here purely on the merits of being one of Chicago’s most successful singles.

It certainly didn’t suit everyone’s taste. But, for those who it did, it became a song that was played nonstop. According to one commentator, Robert Lamm, who wrote it based the melody on The Beatles’ song, “You Won’t See Me.”

5 State of the Union

This was a track from Chicago V that was released in 1972. I have included this song as it shows they were able to produce some funky stuff as well. This has some great drums and bass on it, almost Average White Band in the way it sounds.

There was a time they considered themselves social commentators. They spoke out against injustices, war, politics, and those hidden faces who are “in control.” They wanted to tear the system down and find leaders who were not corporate dummies to represent the ‘ordinary man.’ 

And they wanted truth and honesty in those that lead. Released in 1972, it is still relevant today, only probably more so. This is great stuff from a band that, at the time, was still showing their musical expressiveness and creativity.

6 If You Leave Me Now

By the time the album, Chicago X, had arrived, the die had been cast on their public persona. By most people, they were established more as a pop group, with a bit of rock and jazz around the outside.

The downside of singles…

There was a high proportion of people who didn’t buy albums anymore. They sometimes bought singles or just listened and maybe recorded the songs they wanted from the radio. 

Therefore, the band’s style and performance were determined by what they heard through the media. If you couldn’t get to see them live, as most didn’t, all you knew of Chicago was the singles. 

And, these are not being picked to highlight the band’s musical talents, of which there were many. Record companies were only ever in it for one reason, but now it has become an obsession. Money. I wonder how that sat with the band and its dislike of Corporate America?

But This Song

Some thought they were not the band they were in 1970. But, even they had to admit they did write some good songs. And this was certainly one of them. Furthermore, the quality of this song makes it a standout Chicago song of their ballad period.

Great vocal and lyrics, nice French Horn, and just about everything you could wish for in a song like this. It had a much wider release plan and achieved #1 status in America and the UK, and several other countries. 

In many ways, other than a few early singles, this was the first that many people knew of Chicago. And this style of music is what they thought they were all about.

Goodbye Rock and Jazz

It seems that the change was final now. Maybe they had decided they were too old to be the rock band they had been. From here on, it was pop that was suited to the radio. Regardless of the style, it’s one of the best Chicago songs of all time.

7 Hard to Say I’m Sorry

For this track, I am tempted to say, “read the notes for the last one.” Some commentators say that Chicago dominated the 70s. I’m not sure where they get that from. 

They were successful and, in some circles, very respected but certainly didn’t dominate. Led Zeppelin, Pink Floyd, Fleetwood Mac, and in pop terms, Abba, were the bands that dominated. But Chicago had earned their place a level or two behind those, which is no bad place to be.

Another Big Hit

But this song was another big hit for them. They were now settled into a style that was instantly recognizable as theirs.

Number one in America, #4 in the UK, and a good chart position in a dozen other countries. And the reason? It was a very good song, well played with an effective piano part and powerful production.

Released in 1982, it gave the band their first #1 since 1978 and won a few awards for its songwriting. Another good ballad that helped to cement their position in pop music.

8 25 or 6 to 4

On the Isle of Wight, Wednesday the 26th of August and Thursday the 27th in 1970 had been good. We had seen, when we could and weren’t otherwise engaged, some new bands. Some would go on to better things.

Friday the 28th

On an important day, I had only managed to see a little of Rory with Taste. The schedule had been adjusted, and Tony Joe White was on next. He was using British musicians, including Cozy Powell, on drums.

Next up was a band we had not heard of before. I was busy and only heard their set in the background. Very Blood Sweat and Tears, I remember thinking. It was good and with plenty to admire with its smooth jazz-rock feel.

The Earth Moved

But then they hit us. They broke into “25 or 6 to 4,” and everybody just stopped. This was something else. Everything was just shaking as those horns blew us all away. Stunning was the only way it could be described.

If we didn’t know them before, then we did now. When this came out as a single, I rushed out and bought it. And, I rarely bought records. 

They might have ended up with a reputation for being a ‘pretty ballad band.’ But, there was a time when they could rock with the best of them. And, in Terry Kath, a guitar player who certainly could. In my view, it was a great performance, and it is one of the best Chicago songs of all time.

9 I’m A Man

So, we come to the end of a list of songs from a band that was really two bands. One followed the other. This was how they finished the set at the Isle of Wight. After “25 or 6 to 4”, not many thought it could get any better. It did.

First released in 1967 by the Spencer Davis Group, we all knew the song. They had done a very good job of it, but this was something else. The percussion was everywhere as the horn players changed to a variety of things to hit. 

It Was All Happening

Terry Kath’s screaming over-driven guitar, some heavyweight Hammond organ presence, and powerful drumming. Members switched around, taking turns on vocals. It was all happening. You began to wonder, “what next?” Once again, we were spellbound.

It wasn’t successful the first time around on the first album. But, it was released again as a single after their second album made the charts. In the UK, it went to #8 but only made #48 in their homeland.

10 Fancy Colours

11 Make Me Smile

12 I Don’t Want Your Money

13 Free

14 Sing A Mean Tune Kid

15 South California Purples

16 In The Country

17 Loneliness Is Just A Word

18 Questions 67 And 68 (Live)

19 It Better End Soon – 2nd Movement

20 25 Or 6 To 4 (Live)

21 While The City Sleeps

22 Dialogue (Part I)

23 Dialogue (Part II)

24 State Of The Union (Live)

25 Alma Mater

26 Goodbye

27 What’s This World Coming To

28 Thunder And Lightning

29 Gently I’ll Wake You

30 Love Me Tomorrow

31 No Tell Lover

32 Stay The Night

33 Prima Donna

34 Niagara Falls

35 Forever

36 Take Me Back To Chicago

37 The Pull

38 Mississippi Delta City Blues

39 Colour My World

40 Something In This City Changes People

41 Listen

42 Poem 58

43 Wake Up Sunshine

44 Movin’ In

45 A Hit By Varèse

46 All Is Well

47 Memories Of Love

48 Travel Suite

49 Lowdown

50 Hard Habit To Break

Looking for The Best Songs of All Time?

We can help. Take a look at my thoughts on the Best Cat Stevens Songs of All Time, the Best Dean Martin Songs of All Time, the Best Fleetwood Mac Songs, the Best John Legend Songs of All Time, and the Best Louis Armstrong Songs of All Time for more great song selections.

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Best Chicago Songs of All Time – Conclusion

Things had begun to change in the 80s. Perhaps, as I said earlier, they felt they were getting past the rock-jazz thing. But, it is a little hard to understand why they left that great sound behind to become a ‘ballad’ band.

Opinion and conjecture… 

As I said, they were more like two bands from different periods. Rock Jazz changed into a Ballad Band. But what a ballad band they became. They produced some wonderful songs, and they became instantly recognizable. Those ballads like “If You Leave Me Now” and others are great Chicago ballad songs

But for me, whenever anyone says ‘Chicago,’ I go back to that Isle of Wight August day. And to “25 or 6 to 4” and “I’m A Man.” In my opinion, Chicago at their very best.

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