Even though we rarely traveled anywhere glamorous (ex: Dearborn, Michigan for my dad’s dental convention), my mother had a custom when we arrived at our hotel. She would make my dad and us four (VERY) cranky kids wait in the lobby - often for over an hour - while she scouted out all the available hotel rooms to ensure we got the ones with the best views.
She wouldn’t settle when it came to views. She even uprooted our family from a brand new shiny colonial home in central Glencoe to a (VERY) beat-up mid-century house a mile away - because the house overlooked Lake Michigan with the most amazing views. There’s something fundamentally different about living on the lake. It’s not just the view—it’s the presence. And she believed in it.
Water views, in particular, make the routine of every day living, well, special. Experiencing Lake Michigan all day - and every day - fundamentally adds to your quality of life. Sweeping, cinematic views of Lake Michigan feel less like a feature and more like a daily event. Sunrises that look staged. Water that changes mood by the hour.
And prices… that don’t quite make sense.
Because here’s the truth: Chicago condo high-rises with lake views are, at this moment, one of the great values in American real estate.
That’s not hyperbole. It’s math.
Compare what you can buy here to New York, Miami, San Francisco—pick your skyline. In those cities, a direct water view is a luxury tier reserved for the top of the market. In Chicago, it’s… surprisingly accessible. Not cheap, necessarily. But attainable in a way that feels almost out of step with the experience itself.
I’ve had clients walk into a high-floor condo, glance out the window, and—without a word—just stop. Conversation pauses. Phones lower. Something shifts. Because no matter how many times you’ve seen it, that expanse of water meeting sky still lands. Big time.
And then there’s the practicality.
Many of these buildings offer a level of service and ease that’s increasingly hard to replicate: door staff, maintenance, security, amenities that quietly simplify life. Of course, no market is perfect. High-rises come with assessments, building politics, and an abundance of jabbering yentas in the elevators who are confident they are making the world a better place.
But those factors are reflected in pricing—they’re baked in, discounted even. Which is precisely why the opportunity exists.
Because markets don’t stay misaligned forever. At some point, people remember what they’re looking at. They remember that water views are finite.
So if you’ve been curious, or even casually browsing, it might be worth a closer look. Because every so often, the market offers something that feels… a little off. In a good way.
And right now, 30 stories up, looking east over the lake, Chicago is doing exactly that. It’s an opportunity even my mother would jump on.
Have a great weekend!
Best,
Brad
