Moving from Chicago to Oak Park, Illinois

Moving On from Chicago Living

If you're watching this, you probably love Chicago — the neighborhoods, the food, the energy of living in a big city. But something's changed. Maybe it's the space, maybe it's schools, maybe it's just time for something different. But you want to do that without giving up everything that you love about urban living.

I'm Scott Berg. I grew up in Oak Park and River Forest both. I lived in Chicago for fifteen years, and I'm back in Oak Park for the last twenty. I've helped hundreds of Chicagoans make this transition. Let me show you why.

A Quick Background

Quick background: I'm not a suburban broker who's going to tell you that Chicago is dangerous and the suburbs are perfect. I lived in the city for fifteen years. I loved it. I still love it. I'm a second-generation Oak Parker. My dad grew up here. I went to OPRF. My mom taught school at Lincoln School, and three of my kids went through Whittier, Brooks, and then Oak Park and River Forest High School.

So when I talk about Oak Park, I'm not selling you on a neighborhood. I'm telling you about a place that's shaped my family across three generations. I've closed over 1,700 transactions in 20-plus years. I'm licensed across the entire Chicago area. Because most of my clients aren't just buying in Oak Park — many are selling in Chicago at the same time — I'm uniquely positioned to help them with both transactions.

Why Chicagoans Move to Oak Park

Here's what I've learned after hundreds of these moves. Chicagoans don't just move to Oak Park because they're done with city living. They move to Oak Park because it's the only place outside the city that feels like the city: tree-lined streets, walkable downtown with independent restaurants and coffee shops, a dense grid you can navigate on foot, real architecture — not just boxy new construction — and a diverse, civically engaged community that's been intentionally integrated since the 1970s.

If you lived in Lincoln Square or Lakeview or Bucktown, Oak Park's going to feel familiar in a way no other suburb does.

Five Things You Gain

One — Space. For the price of a two-bedroom condo in Lincoln Park, you can own a single-family home in Oak Park with a yard, a garage, and a front porch. Real space.

Two — Schools. OPRF is consistently ranked among the best public schools in Illinois — top-tier academics, nationally recognized arts programs, strong athletics. For a lot of my clients, the math is simple: Oak Park property taxes versus Chicago private school tuition, and Oak Park usually wins.

Three — The Commute. Many people are surprised by the fact that Oak Park is nine miles from the Loop. I can actually walk to the city border from my house in a couple of minutes. The CTA Green Line, the Blue Line, and the Metra all run through here, as well as the 290 Expressway — and even side streets are easy to navigate downtown. You can be downtown in 20 minutes, O'Hare in 20 to 25, and Midway is 20 minutes south. It's generally one of the best commuting locations in the entire metro area.

Four — The Architecture. Oak Park is the largest collection of Frank Lloyd Wright buildings in the world. But beyond that, block by block, you can see ten, fifteen different kinds of homes on a given block — Victorians, Craftsman bungalows, four-squares, Tudors. You name it, you're going to find it out here. You're buying a piece of history, not a builder-grade box.

Five — The Community. After years of Chicago's transient rental market, my clients tell me Oak Park is the first place that felt like a real community. Neighbors who know each other, civic engagement that's actually engaged, local events people actually show up to.

What I'll Be Honest About

Now, I'm going to be honest with you, because you definitely deserve it. Property taxes in Oak Park are higher than Chicago. That's real. It's one of the most important numbers to understand before buying here. When I work with clients, we run the numbers side by side so you can actually understand your carrying costs.

Oak Park isn't perfect. It's a real community with real issues, real budget debates, and real opinions. But that's also what makes it a community. It's not a master-planned subdivision — it's a 120-year-old village with character and complexity. The clients who thrive here are the ones who came here looking for that, not the ones who expected a frictionless suburb.

Two Transactions, One Expert

Here's the other thing I want you to understand, because it's the part that trips a lot of people up. Moving from Chicago to Oak Park, many times, isn't one transaction. It's two. You're selling a place in Chicago, buying a place in Oak Park, and the timing between these two is where it can get stressful.

Some people use two different agents — one to sell, one to buy. And this creates a coordination gap: two people who don't talk to each other, working on two halves of the same move. I know the Chicago neighborhoods, and I'm uniquely positioned to help you handle both sides of the transaction — your Chicago sale and your Oak Park purchase — as one coordinated transaction. Same strategy, same timeline, same person managing the whole thing. No gap in between, no miscommunication. That matters immensely for a clean move.

Next Steps

If you're thinking about moving to Oak Park, here's what I'd recommend. Watch the rest of this video — that won't take very long. Then go and explore the rest of the page. There's a detailed breakdown of various infrastructure elements about Oak Park. And throughout this website, there's a lot about different neighborhoods of Oak Park, different business districts, and more.

When you're ready to actually talk it through — even if you're a year out — book a free consultation. No pressure, no pitch. Just an honest conversation about your situation, timing, and whether Oak Park is actually the right fit. I'm Scott Berg. I've lived this move myself, and I'm excited to help you make that same transition. Talk soon.