Jimmy Buffett in Concert

The Chicago summer is winding down and I’m busy trying to check everything off my “summer to-do list.” As I think over the list in my head, there is one activity that I didn’t do this summer that I have done almost every summer since 2002: Go to a Jimmy Buffett concert.

My first Jimmy Buffett concert was in 2002, the summer I first moved to Chicago. It was an impromptu decision to go. We made the decision to go late one afternoon and then some friends and I hopped on a bus leaving from a bar in Lincoln Park and away we went. So began a great tradition.

The only song of his that I knew when I went to that first concert was “Margaritaville.” But the thing about Jimmy Buffett concerts is that they really aren’t about the songs, they’re about the experience.

  • The people watching
  • The elaborate tailgates
  • The margaritas
  • The slip n slides
  • The ski shots
  • The inflatable parrots and sharks

By now, I think I can officially call myself a Parrothead. I know the words to most of his songs now. My favorite is “Changes in Latitudes, Changes in Attitudes.”

I saw him perform the first ever concert at Wrigley Field in 2005 and have seen him twice at Wrigley Field since then as well. I have seen him play at soccer fields in Bridgeview and in Frisco, TX and been to too many of his concerts at Midwest Bank Amphitheater in Tinley Park to count. I’ve also seen him play in Alpine Valley, Wisconsin and in Las Vegas.

So much Jimmy Buffett!

It was fun to go back and relive so many great memories as I was gathering photos for this post. Lots of the memories made me smile and I can’t help but but be grateful to have had so many opportunities to go over the years.


My first Jimmy Buffet concert. We are such babies in these photos. There are two things that are almost certain though:

  1. It’s not water in those cups
  2. Joe’s shirt is missing buttons, as was typical circa that time period.


Buffett’s first show at Wrigley Field. We pre-partied at a friend’s house since you can’t really tailgate outside of Wrigley. The show was really fun though! We all look young here too!


I cannot find photos from the concert in 2008 but I remember it well. The reason I remember it was because as was usual back then, we went to the venue without tickets. We figured we would just buy them there. Well, tickets ended up being really hard to find that night. Joe was finally able to get us tickets and then somehow between him buying the tickets and us going into the show, I lost it. Yeah, not a good situation. I deserved to be left in the parking lot. BUT, it all turned out okay. I had gone to the restroom and since I didn’t have pockets in the dress I was wearing, I put the ticket in my bra…and then promptly forgot about it. Ha! Oops! I remembered just as we got to the gate. Crisis averted.


My sister, Amber, and my future sister in law, Beth, joined Joe and me for the concert this year. From the looks of the photos, it was REALLY HOT that day.


Excuse the overexposed photo. We are so spoiled by nice cameras on our phones these days. I spent the afternoon watching Sara Watson play soccer in the northern suburbs and then drove down to Tinley Park to meet Joe and Rene for this concert. It was really warm that day too.

buffett with rene


The worst Jimmy Buffett concert of the bunch I’ve been too! It was at Northerly Island right after that venue opened (the former Meigs Field airport for those who remember its demise). It had rained for several days before the concert and it was not just wet, but insanely muddy. Our feet were covered in it. Our flip flops kept getting stuck. The bathroom and beer lines were crazy long. And we couldn’t really see the stage or hear the music. It was a disaster. We left early and I have stood by my vow to never return to that venue. I think Mr. Buffett made the same vow as he hasn’t played there since.

Fun fact: The photo below was taken before the concert and is the last photo I have of myself before the tailgate of my dad’s truck crashed down on my head. It required stitches and left a nasty scar on my forehead. I think that happened the next weekend.


I saw him perform twice in 2015 – once in Frisco, Texas with my cousin Deb and friend Jenny and then later in the year in Las Vegas with Joe and Chris. The Frisco show was fun. The show in Las Vegas was indoors, which I didn’t like. His shows are better outdoors. It just fits with his vibe better.

buffett in dallas

Las Vegas


We went back to Wrigley Field in 2017, this time with my sister and our friend Meagan…and yes, this is the third one in a row in that same shirt. I guess I should have consulted prior photos before deciding what to wear?! We hung out with Joe and Chris at the bar before the concert.


Joe and I met up with a bunch of his friends from the South Side for another concert at Wrigley Field in 2018. As you can see from the photos above, he and his wife, Chris, are my favorite Jimmy Buffett concert buddies. I have been going with him from the beginning and he is the reason I am a Parrothead today.

So which was my favorite?

That is way too hard for me to decide! There were so many great times and laughs throughout the years. I’ve loved all of them and I hope there are many more to come as well!

Want to keep reading? Check out a couple of my favorite posts – a Letter to My Younger Self and Adventures in Dating After 40.

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Jimmy Buffett at Wrigley Field

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Meet Carmen

I’m Carmen, the founder of this blog and the Vicariously Through You community. I am so glad you’re here!

I currently live in Chicago, IL, USA with my Maltipoo pup, Stella. I am 40-something, single and do not have any children.

When I am not working on this blog and growing the Vicariously Through You community, I work as a Financial Analyst. In my free time, I travel as often as I can, often as a solo traveler. I enjoy rainy days, plain green tea, Chicago Cubs baseball and books with happy endings.

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