A Windy City Production

An unlikely spring break in the urban playground that is the City of Chicago.

Apr 01, 2025

There are two types of people: those who use their plane time to get as much work done as possible and those who space out and do nothing. Guess which one I am? Well, if you guessed the latter, you would be correct. My husband likes to be productive every minute of his life and is always working on flights, while I am always trying to find moments when I can be as unproductive as possible :).

All this is to say that I’m going against my nature by using this time, while I’m on the plane, to write. But it’s that time of year when every moment is precious, and I will absolutely not have time to write once I’m on the ground in Bozeman.

So, I want to give you guys a recap of our Chicago trip, but before that, I want to acknowledge the beautiful celebration we just came back from in San Antonio, where my parents celebrated forty years of Chabad-Lubavitch of South Texas. This is such a huge milestone. It’s hard for me to put into words the awe and admiration I have for my parents and what they have accomplished. I am so happy that I could be there and share in the joy and pride that my family and the whole community have for them.

Ok, so now Chicago: Here’s the thing—you can always rely on an accurate recap from me. I’m going to share the good, the bad, and the ugly. Travel is amazing, but there are always hiccups: the things that don’t go well, the unexpected joys, and the flexibility you need to navigate a family out of their home environment.

How did we end up in Chicago for spring break? It’s not exactly a hot spot for glorious weather and landscapes. The truth is that it really wasn’t the original plan. We were planning a trip to Hawaii to get some well-deserved sun and surf. We even found fantastically priced tickets.

During the planning process, we received an email from Chaya’s school in Chicago announcing the date for her Production (a show they put on every year) and the annual mother/daughter brunch. The date was smack in the middle of spring break. It was obvious that our trip to Hawaii was not going to happen. Of course, going to Chaya’s Production—especially since it was her freshman year—was a no-brainer and where I wanted to be. At the same time, it wasn’t what I had in mind for our spring break. I had envisioned being at the beach, lying in the sun, and having a more laid-back and chill vibe.

It was hard for me to let it go, especially knowing the weather and big-city vibe of Chicago. It took me a while to fully accept the reality, but I got there while also honoring my intuition—knowing that this was not necessarily going to fill the bucket in the way that I was hoping for.

We did have a great time and created special memory-making moments—along with plenty of “oh boy, this is rough” moments.

Here’s a list of some of the places we visited:

Shedd Aquarium – We loved it, and we even did the behind-the-scenes private tour, which was excellent.

The Color Factory – Very fun and different; I had never done anything like it before.

The Ledge – We debated doing the 360 or The Ledge (two different tall-building experiences with slightly different features) and ended up doing The Ledge because it was in the same building as The Color Factory, and it just made sense. It was fun—these things are always a bit overrated, but fun nevertheless.

Ferris Wheel at Navy Pier – It was extremely windy, which made a normally innocent ride on a Ferris wheel quite an adventure. I was of the opinion that the thrill of it made it all the more fun. Chaim Shaul, on the other hand, did not agree and would like to never repeat that experience.

Museum of Science and Industry – I was at the mother/daughter brunch with Chaya, so Chaim Shaul took the kids solo, and they all agreed it was amazing. It’s huge, and one can spend hours there—maybe even days.
Sloomoo Institute – It’s a slime factory and, in my opinion, gross. The kids had fun, and it included making our own slime. I thought it was a bit overpriced.

We, of course, made our rounds at some of the many kosher restaurants Chicago has to offer. Definitely a highlight for the kids. (After once or twice, I’m good and want homemade food.) I was very impressed with the options. I also got to spend time with friends, which was one of my favorite parts of the trip.

For Shabbos, we went to Wisconsin to be with Chaim Shaul’s cousins—that was awesome!

As for the purpose of our trip: Chaya’s Production… The execution and quality of the show were really impressive. It was super fun to see Chaya on stage, shining like the star that she is. I was also extra proud of her because the storyline was complicated and triggering, as the play was centered around an adoption story. I’m impressed with the way she handled it; it certainly couldn’t have been easy. I’m choosing to leave it at that to respect Chaya and her process—not wanting her mom to make a big deal about it, lol. I do think the right conversations and support are happening around it.

I knew this before, but this trip confirmed that we are country bumpkins, and city living is not for us. We had a hard time sleeping in downtown Chicago, where our windows backed the L train. My kids went to sleep with headphones on, lol. The hustle and bustle, the buildings, and the lack of space definitely took a toll on me, and I came home feeling quite exhausted. Traveling with a family is not a vacation, but location does matter. A quieter, more nature-oriented place can do wonders for the nervous system, even with kids in tow. My gut knew that, which is why I initially had such a hard time with the adjustment.

I often get asked: Being that you live in a very rural, more isolated place, when you travel, don’t you want to go to bigger cities with kosher food? And while there are some major perks, we will always gravitate toward off-the-beaten-path locations. This trip definitely solidified that for me.

A Windy City Production

An unlikely spring break in the urban playground that is the City of Chicago.

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