How We Found Our Chicago Home

If you’re looking for a home buying fairy tale, this is not the place to be.

There was no “AH HA! This was THE ONE!’ moment, nor were there hearts in our eyes. In fact, it was more like finding out after weeks of working on your PowerPoint presentation that you accidentally deleted all your work and then had to scramble just to get SOMETHING done. (Side note: that actually happened to me once. It was terrible.)

Once we found out that we’d be moving our family to Chicago, we had to work with some pretty challenging constraints.

1. We have two large dogs. A Pitbull and a Doberman to be exact.

Sharing walls with other tenants? Not likely. Having a yard was a must. Proximity to a park was also relatively important.

2. We want to grow our family…eventually.

No, I’m not pregnant. But we’d like the flexibility so that we don’t have to up and move again when we add a 4th human to our clan.

3. We’ve got a baby.

Safety was a MUST. We didn’t want to always be worried about…ya know. Murder.

4. We’re not made of money.

While we consider ourselves to be savers and just generally financially responsible adults, we had been living off one income while Adam was pursuing his MBA. It’s not like we were just rolling in the dough. Budget was a BIG DEAL.

After discussing our parameters, we knew that finding a turnkey home would be highly unlikely, so a home renovation would probably be in our path.

The Perfect Unicorn

At one point, we actually thought we’d found the unicorn of the mix. We put an offer on a turnkey home we absolutely loved that was also within our budget. It was the AH HA, hearts in our eyes house dreams are made of. Fortunately or unfortunately, our realtor smelled shady business after the developer wouldn’t guarantee their new work through the first winter. After much back and forth, we ultimately retracted our offer and watched our unicorn home fade into the distance. (PS- We drove past it a few weeks ago and it’s still on the market so, clearly, others were disturbed by something there as well.)

Back to the Drawing Board

My sweet husband (Adam) worked diligently and scoured home after home on Zillow. We worked with a wonderful realtor who had been recommended to us by some friends, Jason from Klopas Stratton. He was as discerning (if not more) than we were and helped us look at every home on the market fitting our parameters.

Fast forward to the weekend before we absolutely had to make an offer. It was a Saturday and Adam’s start date for his post-MBA job drew close. We had already sold our current home. Without an offer and a little wiggle room to see the offer process through…we would be homeless.

We started off the day utterly optimistic, climbing in the car with our son to make the three hour drive to Chicago. I was giddy, exclaiming, “We’re buying a house today!”

Fast forward through the, “Is this floor level?” the “Is that weird basement post actually HOLDING THE HOUSE UP?!” the “Absolutely not” and the “Let’s get out of here before we die in here”…

We were sitting on the floor in a VERY purple room of a house we definitely did not want. Even our realtor seemed discouraged.

Spoiler alert: We did not find our home that day.

To read more details of the day click here.

Time to Panic

Adam felt utterly defeated to have poured so much time and dedication into finding the perfect home for our family. What it came down to was….our perfect home just wasn’t on the market at the time.

However, on a solo trip to Chicago, Adam had uncovered a home in immaculate condition that fit all of our parameters. He quickly filed it into the “maybe but not likely” category as it didn’t scream “fixer upper” when he first saw it, and I wasn’t head over heels when I saw the Zillow pictures.

Circling back after our day of disappointment, we were really feeling the pressure of our timeline.

I brought it up and then made plans to make the trek back to Chicago to see it for myself.

The House

When I saw the home for the first time, it had a traditional Chicago exterior. It was built in the 1920’s, so traditional back then was a bit squattier than the lean, shotgun-style buildings that may immediately come to mind.

Entering the home, I met the tenets, an older couple who had lived there for 36 years, and they were only the second owners of this 100-year-old home. As crazy as it sounds, those short interactions really helped sell me on the home.

As we walked around, Jason explained the vision he and Adam had to make it the home we envisioned for our family. What I also saw was a home the owners had really loved. It was clean in the ways you’d expect for a home showing, but you could also see the dedication and care that had gone into the maintenance over time. That is something you can’t pay a cleaning lady to fix overnight.

Families had lived there and loved it. There was rich history, and I could see how the love of the families poured over into the upkeep of their home.

In fact, the couple had turned the upstairs floor into an apartment for their daughter at one point. She had her own staircase, her own entrance, and her own kitchen.

This made the home the perfect renovation spot for us.

Truth be told, I nixed the house in the first place because I didn’t love the kitchen. That, to our family, is the heart of the home. However, if we wanted to expand and renovate the kitchen, we would be able to live on the top floor of the house during that time frame without too much inconvenience.

On the flip side, if we decided not to renovate, the home was in such good condition we could live there comfortably in its current state.

Not to mention, it had a garage to serve us in the winter months, a yard for our dogs, AND it was less than a 5 minute walk from the neighborhood park.

Full Speed Ahead

I walked out of the home and said, “Let’s do it. Let’s buy the house.”

And that was that. Inspections went smoothly given the condition of the home, and before we knew it we were driving a U-Haul into the neighborhood.

For a walk-through of our home prior to our renovations, click here.

Coming Soon: The Vision for our Home

Meet Jen

I’ve always had a love affair with creation. Since I was a child, I handmade my gifts or combined toys to design something new. Fast forward twenty years, and I’m still making my gifts every holiday and designing new ways to do things.


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In order to grow my small business, I earn revenue in a few different ways. I publish sponsored posts from time to time, which are always labeled. Sometimes I earn an affiliate commission on the sales of products or business resources I link to. I only feature items I genuinely love and want to share. Thank you for reading and supporting my small business!