One way to approach this weekly column is to find a news hook and a set of properties that match it. Another is very service-oriented, with an eye on space and affordability. For this one, I'm posing a question that will generate a small set of condos that are simply cool to look at: how high up can you live in Chicago?

Right now, if you set your slider to the 50th floor, there are a fair number of options you don’t have to be extremely wealthy to afford (though be wary of HOA dues). You can even scrape the 70th floor for quite a bit more.

The downside, for some, is that these living spaces typically don’t have a lot of character. They're big investments without the lived-in vernacular architecture you might find in a two-flat. To borrow Stewart Brand’s phrase, they don’t learn. But that might be fine if you're looking out the window most of the time.

175 East Delaware Place, Apt. 6802, $569,000

For just over half a million, you can get a three-bedroom, two-bathroom condo in the Hancock Building, all outfitted in sleek ‘80s marble and mirrors (including mirrored bathroom under-sink cabinets). The place boasts incredible views of the lake, the top of almost every other skyscraper, and with all those mirrors, yourself. The catch? The HOA dues are more than $1,400 a month.

505 North Lake Shore Drive, Apt. 6702, $2.5 million

For a lot more than that, you can get a 67th floor condo in another modernist icon: Lake Point Tower. The additional couple million gets you five bedrooms, four bathrooms, and some of the best views of the city. The master bedroom has a downtown view; the second bedroom looks immediately over Navy Pier. The dining room also has a view of the Pier, which wraps around into the kitchen’s view of the north lakeshore, putting the building’s famous curves to use.

225 North Columbus Drive, Unit 5607, $699,000

Seven bills will get you more than 1,000 square feet in Jeanne Gang’s Aqua tower, enough for two bedrooms and two bathrooms. That takes a big bite out of the kitchen, but at least when you’re cooking you can look out at what you’re really there for: a wraparound living area (and balcony) with a 180-degree view of the lake. (There's also a great view of Gang’s new Wanda Vista tower, so it’s not for grass-is-greener types.)

405 North Wabash Avenue, Unit 5112, $285,000

In the architectural shadow of the Wrigley Building and Trump Tower, this very 1970s high rise blends in to River North. Perhaps that’s why you can get a top-floor condo for less than $300,000, with HOA dues under $500 a month. It’s a respectably sized 750-square-foot one bed, one bath; if that’s not enough space, there’s a storage unit on the same floor, and it comes with a parking space. The tradeoff is a tiny, dated kitchen that clashes with the rest of the open interior, but the living area next to it brings in a lot of light.

33 West Ontario Street, Penthouse D, $2.88 million

If you’re in the market for a lofted penthouse, here’s your chance. The centerpiece is a living area with 26-foot windows that span the height of this two-story, Bruce Wayne-ish condo. It’s $2.88 million, with four bedrooms, four bathrooms, and nearly 4,400 square feet. And it’s a lot of look, like flipping quickly through Architecture Digest: gold-trimmed millwork in the kitchen, a disco-ball-silver tile wall in the master bathroom, a gothy black-leather breakfast nook with a shiny tin ceiling, and an exposed brick wall, somehow, in the study. If you need a breather, the massive patio is minimalist by comparison.