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

Girls’ Weekend in Chicago featuring Jimmy Buffett

Fun. So much laughter. Lots of good food and drinks. Girl talk….

All of these can be used to describe the weekend I had with my sister and our friend Meagan over the past couple of days. I was so excited for them to come visit!

They got in on Friday afternoon and we headed out for dinner that night at Cafe BaBa Reeba. If you’ve followed my blog, you know this is one of my favorite restaurants and my go-to when friends visit. It’s a tapas (small plates) restaurant near Halsted and Armitage in Lincoln Park. It never disappoints and didn’t this time either.

We followed Cafe BaBa Reeba with some drinks at Merkles. Merkles is a Hawkeye bar on N Clark St in Wrigleyville. The sign behind us in the photo below says “This is Hawkeye country.” I agree but Meagan may not since she is a Cyclone.

Brunch at Tuco and Blondie (on the corner of Southport and Roscoe in Lakeview) is quickly becoming one of my favorite weekend activities. I had been to Tuco and Blondie once before and really enjoyed it so I decided to take Meagan and Amber there on Saturday morning. I’m glad I did because was a hit! I had to laugh when we first got there at 10am because I opened the drink menu and Amber commented “You’re going to have a margarita at 10am with breakfast?” Yes, I was, and I did. And they did too. Apparenty, I previously failed to convey proper brunch etiquette to Amber. ????

I had the passion fruit margarita, Amber had strawberry and Meagan had the regular margarita. All were great and not too sweet (which can sometimes happen with flavored margaritas).

I had the gringo omelette and their famous potatoes. Their potatoes are more like a crispy on the outside but creamy on the inside potato casserole. Delicious!

Amber had the breakfast burrito

We finished brunch with the obligatory photo in front of the mural on the outside of the restaurant. Amber and Meagan coordinated their colors to the mural very well!

Next up, the Jimmy Buffet concert! This is one day I look forward to each summer. I have been to a Jimmy Buffett concert almost every year with my friend Joe since I first moved to Chicago in 2002. I would say that this was probably my 15th concert of his then. Does that make me an official parrothead? ???? It was Amber’s second Buffett concert and Meagan’s first. I was so excited to go with them!

We started the evening with a Buffett preparty drink at Sports Corner. (Nice photobomb by the gentleman behind us. He was very proud of himself for it).

Fins Up!

After a quick stop at the Sports Corner, we headed over to Brickhouse to meet my friends Joe and Chris. Brickhouse is a new bar that opened as part of the Park at Wrigley just west of the stadium (Clark and Waveland for street reference). I was skeptical as we were walking over but I ended up really enjoying the bar and our time there. The music was great! The wait staff was friendly and attentive. The food was good. The drinks were tasty. And it was steps to the entrance of the stadium. Wins all around!

Quick selfie in front of the marquee on our way to Brickhouse

Brickhouse is two stories. We were on the second floor patio pictured here. I highly recommend it if you’re heading to a game or concert or even just in the neighborhood not going to Wrigley.

I love this hula girls headband. (I should have left my sunglasses on for this photo).

Chris and me

My favorite Parrotheads, Joe and Chris

Quick photo with Ronny Woo Woo and my friend, Laura, at Brickhouse.

Time for the concert!

Tuco and Blondie gave away beach balls to its brunch patrons heading to the concert. Pretty neat marketing idea!

Joe and Chris opted for rooftop tickets to listen to the concert rather than be inside the stadium. As luck would have it, they are in the rooftop directly behind us. How funny!

Pretty sunset behind Wrigley

Cool coloring of the crowd during the show

It was such a great weekend. I miss Amber and Meagan already. I’m so glad we had the opportunity to spend the weekend together and have a ton of fun! I hope they come back soon!