How We’re Approaching Our City Home Search

It’s no secret that we’re on the hunt for a house.  We debated on city vs. suburbs, and we think we’ve settled on the city.  Finding a home in Chicago is tougher than you’d think.  It’s a competitive market with high price points.  After we sold our Lincoln Park condo, which we redesigned, we decided to rent for a while.  After 3 moves in 5 years, we’re looking for a home to settle. Here’s how we determined our criteria.

1. Walking the neighborhoods

We live in the city because we love to walk everywhere.  Matt & I (and soon-to-be Emmie!) are bigtime walkers and we love the convenience.  We determined how walkable we want our future location to be why going to different areas, literally walking them and checking out the walk scores on Redfin.  Since we’re walk-a-holics, we want a walk score of 80+.

2. Touring the schools

It’s important to us that Emmie attends a neighborhood school.  Chicago is unique in that kids can test-in or lottery into hundreds of schools in the city.  CPS is pretty tough to navigate.  There’s an intricate CPS rating system, which Matt really studied (and I am eternally grateful for). There’s also a Great Schools rating, which is kind of a Yelp for CPS schools.

To be specific, we made a list of all the areas we wanted to/could live in.  Then, we made a list of the schools in that area and Matt dug into their ratings and their school programs.  For example, only a few schools have Pre-K.  Who knew? But Pre-K is about half the cost of daycare so something that’s super important to know!  Ultimately we culled down a list of about 5 schools we were interested in.  We took it to the next level and toured those schools.  Here’s where it gets crazy…. Each of the schools had the same rating in CPS and Great Schools; however, we only liked 2 out of the 5 schools.  If you take nothing else away from this post, tour the schools!  It’s so important.  While you can test in anywhere or lottery into a magnet school, knowing your neighborhood school is important.

3. Driving the streets… and the alley

Having an easy place to park is important to us.  So, when we have a potential house (before we even call Brooke), we drive the property.  All of our family members are ‘burbs people’ (and I say that lovingly), so it’s important they have an easy place to park.  If you’re not familiar with driving in the city, it’s overwhelming.  Also, I clearly love to entertain and I want a home where people want to be!  If the alley is too tight or the street parking is too hard, it’s a no-go.

4. Knowing our numbers

We have looked at our finances countless times and our lender, Ben Cohen, helps us to understand all of the options.  It’s also important to keep in mind that taxes (which are insane in IL) are almost always 2% of the purchase price.  Ensuring you can afford the mortgage, insurance, and taxes are super important.  If you know us well, this won’t surprise you.  We have a super detailed spreadsheet to help us figure out what we can afford.  It’s been more important than ever since I’ve taken Girl Meets Party full-time and Emmie arrived!

5. Stalking Redfin

The early bird gets the worm, right?  Matt is the hero here, but the two of us skim Redfin every day looking for any potential prospects.  Since we’ve already done steps 1-4, it makes it really easy to know when a house pops up if it’s a good fit or not.

Keep your fingers crossed we find something soon, K?

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.


Let's be friends!


sign up for our newsletter to stay in touch


Where I Shop


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!

%d bloggers like this: