Chicago - The One That Got Away: What Two Boys and a Wrong Turn Taught Me About Finding Home

Where I moved into a Wicker Park walk up with bad radiators and good bones, learned to parallel park on Damen Avenue, and spent my twenties eating at places where the reservation was harder to get than the apartment. Where I became a Chicago person - fully, completely, whole heart in!

I didn't choose Chicago.

Not because I didn't want to. I did. But there was a boy... with a good smile who loved me, nature, and small towns; a commitment I honored even when Chicago was on the table. Unfortunately, he and I didn't work out  ... they rarely do when you're 22 and in love, but the choice to stay true to him and not go to Chicago sent me down a road I never could have mapped on purpose, and I am so grateful to him for that part of our journey together.

The La Crosse move led to promotions. Promotions led to Madison and then eventually Milwaukee. Milwaukee led to Whitefish Bay, and a second home for me at 27, and a career that has now stretched past two decades serving people who are making their own version of the same impossible geographic choice.

Here's the part that still gets me: years later, Chicago called back. The boy, the city, the version of my life I'd quietly set aside ... surprisingly it reached back across the years the way that chapter always does, just long enough to make you wonder...what if...

Here's what I know about the Chicago life I didn't live: it would have been wonderful, expensive, and almost certainly rented for longer than I'd have liked. Who knows if I ever could have afforded a home there?

Chicago takes. That's part of its character and I say that with genuine affection, not criticism. It takes your commute, your parking budget, your patience at O'Hare, and a significant portion of your paycheck in exchange for something magnificent: the feeling of being inside one of the greatest cities in the world. That trade is worth it for the right person at the right moment. It was never mine.

Milwaukee gave back first.

At 27, I bought my second home in Whitefish Bay. I owned something on Milwaukee's North Shore, a neighborhood that, by any honest comparison, holds its own against Chicago's North Shore in character, in beauty, in quality of schools and community at a price that was actually possible on a young professional's income. That matters in ways that compound quietly for decades. Equity. Stability. The particular confidence that comes from a place that is unambiguously yours.

I would not have done that at 22 in Chicago. The math wouldn't have worked. I'd have rented for years in a city that wanted everything from me before it gave me a foothold. 

La Crosse cost me Chicago. Milwaukee gave me a foundation and the love of my life.

I've had a lot of clients over the years who arrive in Milwaukee carrying a version of grief. Not the dramatic kind ... nobody's crying in my car, usually... but a quiet, specific mourning for the city life they're leaving. The walkable density. The cultural calendar that never empties. The feeling of being at the center of something large and alive.

Chicago does that better than almost anywhere. I've never pretended otherwise.

What I watch happen, consistently, over twenty plus years of doing this work, is that the grief transforms. It doesn't disappear;  these clients still love Chicago, still go back for long weekends and concerts and dinners that remind them why they loved it, but it shifts into something more like nostalgia than longing.

There's a difference, and it matters.

Nostalgia is warm. You visit, you feel it, you carry it home with you like a souvenir and it sits pleasantly on the shelf. Longing is restless. It follows you into your mornings and second guesses your decisions and makes the life you're actually living feel like a compromise.

Milwaukee, I've found, quiets the longing. It earns its way into people's lives without announcing itself. And eventually ... usually around six months in, standing in a backyard bigger than anything they had in Lincoln Park, coffee in hand on a Saturday morning with nowhere to be in a hurry and they say some version of "I didn't think I'd feel this way this fast."

They mean: at home. They mean: settled. They mean: I didn't realize how tired I was until I stopped.

Here's the turn I want to make, because I think it's honest and because it's where the story actually lands:

Chicago living is the boy that got away for a lot of buyers.

Not because Chicago isn't worth it...oh it absolutely is, for the right person at the right stage with the right financial runway. But because so many people carry a vivid image of the life they would have had if the numbers had worked, if the commute had been manageable, if the city had given them just a little more room. They grieve a Chicago life that was, if they're honest with themselves, always slightly out of reach.

I understand that grief personally. I chose La Crosse over Chicago and followed my heart at that time with something that didn't last, and for years Chicago sat in the back of my mind as the road not taken.

Here's what I know now, and what I tell my clients, the road not taken is rarely as clean as the imagination makes it. The Wicker Park walk-up would have been charming and expensive. The renting years would have stretched. The wealth building would have come later, or not at all, while the city extracted its toll in commute hours and parking costs and the low-grade exhaustion of living somewhere that was never really a "true fit" for my life goals. 

Milwaukee gave me more

In the spirit of making this useful and not just sentimental, here's what twenty years of North Shore real estate has taught me about what Milwaukee actually offers to some imagined Chicago life, but on its own honest terms:

Ownership while you're still young enough to enjoy it. I bought at 27. My clients buy in their late twenties and thirties regularly. In Chicago, that timeline extends often by a decade, often into a market that has moved further away by the time they're financially ready. Starting the equity clock earlier is not a small thing. Over fifteen or twenty years, it is transformative

A commute that gives you your life back. Eight minutes from Milwaukee's North Shore to downtown. I know and I've said it before, I'll say it again. Because what it represents is real: hours returned to your week, compounded over years, that you spend with your family or your garden or your Friday night fish fry instead of on the Kennedy Expressway.

A neighborhood that knows your name. Milwaukee is small enough that community  is a REAL thing. Your neighbors show up. Your kids walk to school. The places you love remember you. It makes for a wonderful life. 

The surprise of it. Nobody moves to Milwaukee expecting to love it the way they end up loving it. That's actually part of the charm. Chicago is a city you love because it's Chicago because you knew going in that you would, because the reputation precedes it. Milwaukee is a city you love because it earned it without trying. There's something more lasting about that kind of love. Like a good friend. Steady. Calm. Always there. 

Equity that builds while Chicago buyers are still renting. The gap between renting in Chicago and owning on Milwaukee's North Shore, measured over a decade, is a number that changes conversations. I've run it with clients many times. It never stops being life changing. It is. Financial Freedom is where it is at.

I still think about Chicago...

The architecture. The lakefront at dusk. The way a city that size makes you feel briefly significant just by being inside it.

I visit. I occasionally, do a run or event there and yes... I always leave wanting a little more. 

And then I drive north on I-94, and somewhere around Kenosha the skyline shrinks and the traffic lightens and the particular tension of a big city releases from my shoulders, and by the time I cross into Milwaukee County I remember exactly why I live where I live.

The boy I chose over Chicago gave me La Crosse. La Crosse gave me Milwaukee. Milwaukee gave me Whitefish Bay at 27, a career I love, and twenty years of watching people discover the same way I did, slowly, then all at once that the city that was actually available to them turned out to be exactly the right one.

Chicago called back, years later, and I understood that nostalgia had been doing the work all along making the road not taken look like a loss when it never really was. Destiny ~ a sweet friend of mine.

It's a Milwaukee love story and a journey to find home that happened to start in La Crosse, run through Madison and land in sweet ole' Milwaukee. 

The journey has been one of God's great lessons, and to the boys and everyone in it. Thank you, I am so grateful for our moments in life together and the journey.  Three cheers to making Milwaukee home!

Suzanne Powers is a top-producing broker with Powers Realty Group, specializing in Milwaukee's North Shore. She has served Chicago transferees for over 20 years and considers Whitefish Bay the best decision she never planned. Find her at powersrealty.com.