They call it the Windy City! Although the only thing that really blew for us, were pyrotechnics at the Bruno Mars concert. Haha! At Soldier Field. In the most incredible weather. My God it was an event. Buckle up, friends. Chicago was quite the ride.
May 2026
So, we started off the whole trip with new travel buddies. Always fun. Say hello to Scott and Missy. Hello! 👋

And Phillip and I can really blame Scott for this whole Chicago affair. It was Scott who was in the process of buying Bruno tickets only to find they were selling out faster than he could click. That Bruno is one popular guy. Word on the street was Bruno booked his entire 40-stop The Romantic 2026 tour—I mean 40 … that’s a lot—only to find demand wasso high and the tickets were selling out so fast, he added 30 more additional shows almost immediately after tickets went on sale. We hadn’t even been planning a trip to Chicago but once Phillip heard we could get floor seats … IF we moved fast.
What did Phillip do? (Have you met the man … ) He booked. Bam. Done. We were going to Chicago.
Bruno Prep
Funnily enough, we already had a trip booked in early May but we’re apparently in our Travel Era, so two trips in one month is just how we roll nowadays. I only mention the trip TO COLORADO the week before because that’s where we picked up our incredible Bruno Mars concert outfits. If you have NOT been to a big venue concert like this (don’t worry, I hadn’t) let me teach you something: YOUR ATTIRE IS KEY. I did not know this. But, Phillip schooled me up showing me we needed to either get some cool outfits that channel one of Bruno’s many iconic looks or we go red head-to-toe as that’s what we’d heard others were doing for … quite appropriately … the ROMANTIC tour.



Phillip and I decided to channel our inner Bruno. He went with an I Just Might version that was pretty stellar, and I got a bedazzled hat and banging silver books that channeled Bruno’s mariachi style on The Romantic album. [Side note – had I know what Anderson Paak was going to wear on stage … totally would have done that. And, don’t ask, I’m not telling because I’m planning it for Halloween. Our favorite holiday. Heck yeah!]. So check out these rocking numbers we got at one of the many prolific thrifts stores in Boulder, CO.




Loved this pic I snagged of Phillip at the thrift store with the clerk fan-girling over his spot-on Bruno outfit.

Although do know I was trying to get Phillip or Scott to wear this. Both vetoed me (*ahem …. I won’t say the word here that I called them). But, that’s okay – with our sparkle boots and hats, we were ready.


Dinner at The Purple Pig
But, first things first. It is Chicago. We do need to party. For our first night there. We ate at The Purple Pig. The food was immaculate, delicious, incredible. Check out this dish that came out all steamy. Talk about making an entrance!
The atmosphere was lively (although I have to mention a little loud) but the four of us were punch drunk and giddy and just giggles most of the dinner, so we had an exceptional time.







And, I can only hope you find friends that you can laugh this hard with in your lifetime. Missy, Scott, you guys are welcome to travel with us anytime. What a hoot!
Tiki Drinks at Three Dots and a Dash
After dinner we ventured to what will probably serve as one of our favorite spots in all of Chicago – Three Dots and a Dash! Little back story – during Covid Phillip and I got a little (too) into cocktails. We went nuts. Ordered books. Stocked our shelves with eight different kinds of rum—yes, the pot-stilled, the pure, the Agricole, the funky, we had it all. We ordered these two books: Tiki and Smuggler’s Cove—and did cocktails the right way. They’re subtle, herbal, strong. Real tiki drinks are not syrupy or overly sweet. If you’re doing it right, they’re the complete evolution of a party in your mouth, from the beginning quiet notes, to the breakout on the dance floor, to the satisfying appreciation of what just went down. Phillip was in hog heaven at this place. I don’t think we would have gone anywhere else had we been able to get a table. We would have ordered their “treasure chest” (a massive drink actually served IN a chest with eight straws). Next time …







EDM Dance Club
But alas, this time we had after-cocktail plans at Sound-Bar. A high-energy, EDM (electronic dance music) club. It’s a new thing we’ve been doing. Highly recommend. DJs these days are wildly entertaining with their colorful lit-up booths, their entourage up on the stage (think: gorgeous people partying) and their energy and vibe. This DJ—although he looked like a guy that would work at Office Depot, which cracked me up—was super fun, had the crowd jumping and going. And, it was awesome to be able to watch him physically manipulate the tracks and sounds right in front of you. That really added to the energy. And, the ladies had fun getting all glammed up in our clubbing outfits. The straps on my little dress were disco ball. Doesn’t get much better than that!


Day Two: Grant Park
Our first morning there Phillip and I enjoyed a lovely stroll through Grant Park. We stayed at the Hilton Chicago there by the park which turned out to be a fantastic spot for just about everything we wanted to do, particularly the Bruno concert. We walked to and from it, which added to the experience and enhanced it as we didn’t have to worry about parking at all. We just mozied there and back and enjoyed the people watching. It was the perfect spot, especially for mine and Phillip’s morning stroll through the park. I particularly enjoyed these iron sculptures. The artwork consists of 106 towering, headless, armless iron figures created by Polish artist Magdalena Abakanowicz. Each figure is about 9 feet tall, and the installation is called “Agora,” named after the ancient Greek word for a public gathering place. It was installed in Chicago in 2006 and has become one of the city’s most recognizable public art pieces.























Architecture Tour by Boat
Day two we did something Phillip and I have done before, but it was so fantastic, I was actually looking forward to doing it again almost as much as the Bruno Mars concert. It is an architectural tour by water. Chicago has a fascinating architectural history—what with The Great Fire of 1871 that changed the very fabric of the city and the way people lived and built going forward. Some fascinating stats:
The Destruction at a Glance
- Dates: October 8–10, 1871
- Damage: Leveled roughly 3.3 square miles (about a third of the city) and destroyed 17,000 structures.
- Casualties: Approximately 300 lives lost and over 100,000 residents left homeless.
- Financial Loss: Roughly $200 million in 1871 dollars (more than $5 billion today)
Then there was the World Fair that came through in 1893, a monumental event designed to celebrate the 400th anniversary of the “New World” (think: when Columbus first discovered) and demonstrate that Chicago had completely recovered from the devastating Great Fire of 1871. This event attracted over 27 million visitors (million!). Many of the buildings we looked at and learned about were shaped by that history. It was fascinating. Highly recommend this tour if you go to Chicago.

























Deep Dish Pizza at Lou Malnati’s
We also had to (it’s a must) get a deep dish pizza while in Chicago. And this iconic pizza spot—Lou Malnati’s—proved to be the perfect place to cross this important item off our list. NOTE: when they say deep dish in Chicago, they don’t mean Domino’s with the thick crust. This is pizza that I would actually describe as a pie, like with a pie crust that sits on the bottom of a 2” tall pan and your pie filling is cheese, meat, sausage, more cheese, pepperonis, more cheese. Like THAT kind of pie. I never really understood why they called pizza a “pie” until Chicago. Once you have a Chicago deep dish pizza, you understand the pie. It’s all about that melty, stringy cheese people.





And, don’t worry – the calories are all made up so the points don’t matter. *You’re on vacation. Just eat.*
THE BEAN!
I mean … you have to do this every time you go. While Phillip and I try to stay off the beaten path and really experience new cities like a local, some sights are just so iconic it’s worth it go bumble around with the tourists to experience it. The famous mirrored lima bean in Chicago is definitely one. I’m just now learning it’s also called “Cloud Gate” but lima bean is far more fitting. Wouldn’t you agree, lol? Just walking around this thing, looking at the reflection of the city skyline on it, waving to yourself in it, spinning around aimlessly underneath. It’s just fun. And, I can imagine if I lived in Chicago I would come and sit near the bean often to people watch and write. It’s a lovely spot.













Okay, friends, you’ve been patient long enough. Now the Chicago event you really came to see. Us too. Let’s do this.
BRUNO MARS
You know, I don’t really feel like I need to say much here (and, yes, I know I’m the writer) because this was such a visual, audible, visceral experience. Bruno entertained from the very minute he stepped onto the stage (DJ Pee Wee – Anderson Paak, and Leon Thomas did too!). The way Bruno spliced in his old hits, but stayed true to The Romantic vibe and feel was exceptional. The visuals, the big jumbo screens, the pyrotechnics, the fireworks, the confetti in the sky. This was a complete sensory overload from the beginning to the end. Just here – a million pics and videos will never do it justice. But, I will forever be glad I experienced this exceptional artist and all of his creativity from the floor at Soldier Field. Thank you Phillip!


































Also, afterward, we absolutely slayed burgers at this little eatery near our hotel. Took forever for them to make them (know it was near midnight at this point and the city was drowning in red-clad, starving Bruno fans) and we were famished. We tore into these things like hungry hippos, gnashing and clawing and getting it all over our faces. I couldn’t have dreamed up a better ending to that night.

Bruno, you will forever be a legend in my book. And I’m pretty confident it will be years if I ever witness a musical event that spectacular … if I ever do. It would be okay if I didn’t. Trust me. If you were there, you would agree. I can die a happy Bruno fan now.
Thank you again, Phillip–and Scott–for making this all happen!
Day Three: Biking Chicago’s Lakefront Trail
This was another thing Phillip and I had done in Chicago before, but we loved it so much we wanted to do it again. Plus, you saw the pizza and the burgers (and I didn’t even mention our cookie stop at Levain … Phillip is a cookie monster!). Also, after a mind-blowing brunch at The Girl & the Goat, we were due for some physical exercise, lol. Besides, biking this waterfront is not exercise … really. It’s just lovely. They have a well-marked path and lots of people walk and jog it, so it’s great people watching. Funny, though, because we were taking in the sights, the four of us were going kind of slow, and regulars were definitely passing us and scoffing. I mean .. it is still Chicago, cousin of New York, lol. But, they were harmless and we had fun chuckling at our Granny Pack. This is definitely a glorious way to experience the waterfront.













Navy Pier
Once you’re out in the lovely open air biking, you need to go to the cool places. Navy Pier is a fun spot. It kind of feels like Coney Island, like a state fair on a little spit of land. It’s a little touristy, but still lots of fun. And, it has one of the best views of Chicago’s skyline. Worth a spin through, especially on a day as lovely as this.


Wrigley Field
While we didn’t book a game this time, our buddy Scott is a huge sports fan, so we rolled up to the Wrigley neighborhood to check out Wrigley Field and poke around. The sports memorabilia stores were cool and we got some great shots in front of the iconic field.


RPM for Dinner and That’s a Wrap!
Our last night there ended up being our greatest dinner experience, which I think is how you always want it to go. The Purple Pig was phenomenal, don’t get me wrong, but it was a little loud (and, granted, we were giddy and excited it being Night One of the trip, so that has an impact). This evening—after we’d done the boat tour, we’d biked, we’d DJ’d and danced, we’d witness the majestic event that is Bruno Mars at Soldier Field—our metaphorical bellies were already full. Phillip chose RPM, this wonderful, elegant Italian restaurant. They put us in a quiet booth and our server was like silk, slipping in and out wordlessly bringing us every thing we knew we needed, and many we didn’t, as well as stories and quips. She was the je ne sais quoi of our dinner, and the four of us having that hour to reminisce, share stories, laugh, and just recap it all was the je ne sais quoi of our Chicago trip.




What an absolute blast. Well, other than getting delayed at the airport and not getting home till 1:00 a.m. (the day after we took off from Chicago!).

Small price to pay for that epic amount of fun. And, Scott and I had fun snagging this iconic movie shot while in the airport. Just needed to pull my spandex britches up a bit before taking off, but you’re welcome.

Chicago … we’ll be back!



































































































































































































































































































































































































































































































































































































































































































































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