Exploring Two Cities
March 24, 2025
Exploring urban cities can be as much fun as exploring nature. This last weekend while our daughter explored NYC, we had a weekend in Chicago.
A Long Anticipated Trip to NYC
Last year we were excited to sign our daughter up for a trip to New York City being planned by her high school music department.
Unlike many school band trips, this trip would not involve the student doing a performance as part of a competition or an evaluation. Instead it would focus on various aspects of the arts in NYC.
As parents we were immediately sold on the idea, our daughter had a more lukewarm response but was interested in going so we quickly signed up for the trip.
Over the last two months it was on our minds more often until last week started and the final countdown began for both trips.
Oh I forgot to mention that my wife and I started discussing a weekend away in Chicago a few months ago. With everything that’s been going on it seemed like a great opportunity to get away.
NYC Bound
Thursday morning we were all up early which gave me a chance to see Mia before she left and I had to leave for work in the city. I had expected her to be a little more nervous but to be relief she seemed excited. My wife and I really hoped the trip would be filled with great memories.
Before I knew it the day was half over, and they were safely in New York and experiencing different sights and sounds.
I just saw some guy standing on a box with nothing but underwear in times square.
Along with seeing St. Patrick’s cathedral they went to Chinatown. Finally finishing the day with a singing dinner before heading to bed in their tiny hotel room with two full beds for four girls.
Friday Fun
Friday ramped up the fun in NYC with the group getting to go to a skyscraper observatory and the 9/11 Memorial.
Mia also told us she had the opportunity to barter twice! Get those deals! They finished the night up going to see the Broadway show “Hadestown”.
Back here in the Chicago area we worked like we normally do, but were off to catch the 4:37 PM train back into the city. We would be staying the weekend at the Hotel Intercontinental on Michigan avenue.
The train is something I enjoy riding, unlike friends who refuse to take it for varying reasons, I appreciate its ability to bypass traffic. Stepping out of Union Station I convinced Karin to let me show her the upgrades they had made the last year at my office.
I am always talking about different aspects, so it was fun to walk her around and see what I’ve always been blabbing about. After that we were off to the hotel.
The Intercontinental is a grand old hotel that our good friend Heather recommended. We wanted to go to a hotel that had a great spa where we could swim and get some spa treatments. The Intercontinental didn’t disappoint.
After check in we were ready for dinner, trying to get into the “Purple Pig” was a bust with an insane wait time, so we decided to put the pig off until Saturday for lunch. Instead we decided to give one of the restaurants in the hotel – Casa Chi.
Wow, what a great pick that turned out to be. We started with their ahi tuna guacamole that was beyond good. We followed this up with a mind blowing salmon sushi roll and finally hot stone tenderloin tacos that you cook on a super heated stone.
But the real star was the lemon cheesecake desert that was served in a chocolate lemon. The perfect end to our day.
Outsiders & Back to the Future
Saturday started with later for us than it did for Mia. I have to admit to enjoying sleeping in.
In NYC they had a busy day planned with a matinee theatre production of the Outsiders. Mia absolutely loved it.
In the evening they were off to see the New York Philharmonic orchestra in the Back to the Future concert where they played the soundtrack while the audience watched the movie.
Here again they got another great experience where after the show they got to meet Robert Zemekis who talked about making the movie. Wow!
Back in Chicago we started the day with some Starbucks before our scheduled spa treatments. Up on the schedule was a facial for Karin followed by a couples massage.
It has probably been twenty years since I have had a massage, and I was very much looking forward to it. I’ve had some persistence neck and shoulder pain for a long time that I was really hoping that the guy would be able to focus on.
And focus on it he did. While my wife lay on a table next to me getting what I am sure was a nice relaxing massage, Miguel, aka “Iron Hands and Elbows” was giving me the most painful deep tissue massage one can imagine!
The pain was almost unbearable, but I just figured it was either a) normal, or b) because my neck and back were so stiff, so I just endured it counting the minutes until it was over.
I looked over and he was really digging into your back with his elbow.
At the end I could barely get up and I knew I would be sore later, and in even worse condition come Sunday. Returning to the room all I wanted was a scorching hot shower, but it was then they we discovered the only disappointment of the hotel. Terrible water pressure with equally bad hot water. Oh well.
But the day will still young so we headed out to do some shopping on Michigan avenue and have lunch at the “Purple Pig”. Karin had been here before and couldn’t stop talking about it.
And after eating there I now know why. Sublime perfection. I won’t bore you too much with the food, but the Chicken Liver & Bacon Pâté with Fried Sage + Grape Mostarda was remarkably well portioned.
We followed this with a peach and cheese combination that if I am being honest was very pretty, but a waste of money. Three toothpick portions was a disappointment.

But the Spanish Octopus with Marbled Potatoes, Jalapenos, Sambuca + Chimichurri has to die for. With or bellies full we decided to drop the shopping bag at the room and walk over to Navy Pier.
Karin has seen that they were featuring women artists so we thought it would be cool to see what was available. On the way over we started seeing more and more people covered in a multi-colored array of chalk dusk.
It was the Holi festival.Holi Festival @ Navy Pier - LINK Attendees powdered in many hues dance, grin at Navy Pier, ushering in the new season and mending relationships in ancient Hindu rite.
Which was really cool to see, especially so after getting to Navy pier and finding that the woman’s showcase was more crafts that arts. Ah well, it was good to get out and walk.

By now I was really starting to feel the after effects of the massage. My back and shoulders was killing me. I actually had to ask Karin to slow down while walking (which never happens) and had to sit down to take a break for a bit at Navy Pier. After a short cab ride we were back at the hotel.
Dinner at Mike’s
Having witnessed the achievements of the Bulls in the 90’s we couldn’t pass up trying the other restaurant at our hotel - Michael Jordan’s Steak House. An absolutely beautiful architectural stairway led us up to the kind of ambiance you would expect from a fine steak house.
Drinks were mandatory and delish. As was my baked french onion soup and Karin’s Caesar salad. The real star however was the ten ounce filet that we split and the mashed potato trio (roasted garlic, lobster, sweet potato).
The steak practically melted in our mouths and what could be better than that potato combo? We were stuffed but decided to order Mascarpone Cheesecake with brown butter streusel, glazed berries, strawberry & blackberry coulis to go to have after Drunk Shakespeare.
Drunk Shakespeare
After getting a random private car to drive us to the theatre for $25 (thank you hotel bell captain!) we rode over in style. Probably the nicest and most expensive BMW we have ever been in to the Lion Theatre for Drunk Shakespeare.
Tucked between Taco Bell and Panda express the no-nonsense theatre was mysterious, shabby and equal parts exciting and enticing.
Stepping through the entrance into the bar and as quickly into the theatre you really got to appreciate how intimate of an experience it would be. And by that I mean small. Our seats were center stage, right by the chairs for the King and Queen.
The issue was that it was a wooden bench with no back support. I immediately knew I was in for trouble with as bad as my back felt earlier in the day. And I was right, by the end of the night my back was trashed.
But the performance was a delightfully funny and raunchy rendition of Macbeth with some surprise songs sung insanely well. It was a blast to watch.
And exactly the type of thing that makes us miss living in the city so much. I think too many people view Chicago through the lens of traffic, or museum visits or concerts with thousands of people. You know the events where getting to the city sours, or at the minimum takes away from the experience.
But when you live in the city, or at least visit it and take away that toil, your left with interesting experiences that just burst from every corner of the city.
With Saturday in the bag, we headed back to the hotel to collapse into a deep sleep.
9:30 AM? How?
We were dead to the world. The combination of fresh air, mini adventures and massages left us tired and exhausted. We both slept like rocks. I woke to a incredibly sore body.
In New York the group was headed to Studio 54 of all places to meet one of the cast from the Outsiders for Q&A session.
In Chicago we called for a late check out and headed down to the pool to have a swim. The pool in this hotel is something straight out of the gilded age.

Check out what this articleAWA Article - LINK has to say about the pool:
“At the time, the pool was one of the highest indoor pools in the world, and its fourteenth-floor location was heralded as an engineering achievement. Engineers developed a system similar to the support system used by railroad bridges to support the large quantity of water at the 14-story height.
The area around the pool showcases preserved classic architecture from the 1920s including a terra cotta fountain of Neptune, Spanish hand-painted tiles, marble pillars and stained-glass windows. It is known to many as the Johnny Weismuller pool, a testament to the famous Olympic athlete who trained in its waters.”
What surprised me most was that the pool was ten feet deep at one end. Something you don’t expect to see in a pool with swim lanes these days. In addition to the architecture which I am sure you will agree is stunning, the green fish scale stained glass windows was a real treat.
Wrapping Things Up
After checking out of the hotel we had the Bell Captain hold our luggage and went to have a bite to eat at the Albert restaurant. H&M Bagels with cream cheese, lox and sliced cucumbers along with eggs Benedict hit the spot.
The plans were to visit a museum but we honestly were pretty tired, so we decided to just grab some Garretts popcorn and head home. The rain that started only further cemented our decision.
It was a fabulous weekend but we were ready to head home. A quick train ride and Uber ride and we were back. A few hours later we picked up our daughter from her adventure. A great time all around.