The legendary newspaper columnist Mike Royko coined the term Bungalow Man to describe a particular urban species, one that lived in the general vicinity of Milwaukee Avenue and shopped at Sears — a man with a more authentic connection to Chicago than the cosmopolitan High-Rise Man, with his membership to the East Bank Club and subscription to Chicago magazine (ahem).

Defined by sturdy construction and elegant touches like low-pitched roofs and ornamental brick façades, bungalows — most of which were built from the 1910s to 1940s — represented an elevated American dream for working-class families: They offered privacy, front and rear yards, and room to expand. Long stretches of the squat homes, with their meticulously maintained lawns and gardens, embodied Chicago’s Urbs in horto motto.

Bungalows still make up about a third — or 80,000 — of the city’s single-family houses, according to the Chicago Bungalow Association. One need only look to the outer perimeter of the city — the aptly named Bungalow Belt — for a plentiful supply.

The Chicago greystone, named for the slate-colored Bedford, Indiana limestone covering its façade, could be summed up as an aspirational palace for the Everyman. When the style first rose in popularity, in the late 19th century, Victorian flourishes carved into the heavy stone were intended to signal high-quality craftsmanship and long-lasting quality. Even with those elegant touches, the mini manses were designed to be duplicated on a large scale. They were built en masse throughout Chicago between 1880 and 1910, largely thanks to the city’s robust rail network, which created a direct connection to the limestone source near Bloomington, Indiana. Builders also employed crafty, cost-cutting engineering methods like using regular brick for the rear and sides.

The greystone could be viewed as Chicago’s response to the Brooklyn brownstone. Both are characterized by the use of local materials, and the greystone, like its East Coast cousin, comes in a wide variety of shapes and sizes, ranging from small single-story residences to majestic mansions. Two- and three-flat greystones are particularly common, making these architectural gems accessible to middle-class families.

In historically blue-collar and immigrant neighborhoods throughout the city, detached single-family workers’ cottages can be spotted standing among simple two-flats and other similarly affordable housing types. Predecessors to the bungalow, the cottages are modest in size — most come in under 1,500 square feet — but also dignified and aspirational in their variety of configurations, as well as their range of ornamentation, from Victorian to Italianate. These homes flourished particularly in the so-called burnt district, as communities quickly rebuilt in the expanse of central Chicago destroyed in the fire of 1871.

Though the cottages are decidedly compact compared with, say, a modern townhouse, they were viewed as a step up from the squalor of tenement life, providing families with privacy and enough space to cook, clean, and sleep comfortably. Otherwise, everyday life — work and play — took place outside of the home. These days, they’re a good starter house for a young couple that spends more time out and about than lounging around.

The Prairie school, widely considered to be the first truly American form of residential architecture, was born in the Chicago area. It was in Oak Park that a young Frank Lloyd Wright built his home and studio and fleshed out his early design principles — a philosophy that sought to integrate houses with their natural surroundings instead of distract from them.

A dramatic departure from the trends of the Victorian era, which favored ostentatious elements such as towering turrets and gingerbread-style adornments, the Prairie school celebrated long and flat rooflines, earthy colors, and frill-free façades. The homes included upscale creature comforts like electric lighting and carefully thought-out floor plans that favored movement and flow.

And while Prairie homes were strikingly modern for their day, the dark, compartmentalized interiors are a stark contrast to the current trend of open floor plans and bright white interiors. Since these are one-of-a-kind homes, ownership can be more challenging than with simple, fuss-free new construction. (Art glass windows aren’t exactly an off-the-shelf product if you need to replace one.) However, for many buyers, particularly those with a fondness for architecture and design, Prairie school residences are nothing short of dream homes.

If necessity is the mother of invention, then thank Chicago’s dramatic population boom between the fire of 1871 and the 1933 world’s fair — a period that saw the arrival of nearly three million new residents — for the multifamily flat. The innovation of balloon-frame construction allowed housing to be easily built, enabling developers to cram blocks with homes to keep up with the influx.

Noted for their bay windows, steeply pitched roofs on the wood versions (gently, if brick), and simple floor plans, multiunit residential flats were seen as a path to the American dream — an opportunity to build equity and achieve financial security through rental income, with the homeowner living on one floor and tenants living on the others. This isn’t to say that these practical structures weren’t well conceived or well constructed. Be they wood frame or brick, they remain one of the most durable, most economical, and most pervasive housing types in Chicago.

As recently as 2012, two-, three-, and four-flats represented the most plentiful residential form in the city, according to a report from the Institute for Housing Studies at DePaul University. But as housing trends change, these dependable buildings are often targeted for demolition or conversion into single-family homes, particularly in quickly appreciating North Side communities. The postrecession construction explosion has been a large reason for the drastic decline in Cook County, which lost more than 26,000 units in flats from 2012 to 2017.

The modernist movement — led by Ludwig Mies van der Rohe, who came to Chicago from the Bauhaus in Germany — marked the rebirth of the skyscraper in the city that invented it. His “less is more” philosophy signaled the end of the whimsical flourishes and ornamentation favored by the Chicago school (Louis Sullivan, Daniel Burnham, and the like) and helped usher in a new era of minimalism: strong vertical lines, exposed steel exoskeletons, and lots and lots of glass. Inside, the units featured open floor plans (think Don Draper’s swinging, party-ready bachelor pad in the later seasons of Mad Men) and abundant natural light. Primarily found along the lakefront, these soaring structures also represented a different type of postwar city living that included sweeping skyline views, ample services, and excellent transit access.

With their hundreds of units, midcentury towers are the manifestation of the futuristic “city within a city” ethos, which envisioned buildings that incorporate every amenity — a dry cleaner, convenience store, sky-high pool — urbanites need to live comfortably. (The building formerly known as the Hancock even has its own polling place just for homeowners on Election Day.) Despite the architectural significance and plentiful creature comforts, entry-level prices don’t exclude budget-conscious buyers. Read the fine print, though: Steep monthly assessments can offset initial savings.