After Chicago gobbled up outlying villages north, west, and south of the city in a grand annexation of 125 square miles and 225,000 people in 1889, it found itself with a mess of roadways with duplicate names, houses with the same numbers, and no systematic pattern with which to organize its streets, according to the Electronic Encyclopedia of Chicago.

After two decades of confusion, itinerant Urban Planner Edward P. Brennan stepped in with the proposal for a uniform numbering and naming scheme that, in sensible Midwestern fashion, registered both road direction and distance. Part of the 1909 Plan of Chicago, the initiative is variously known as “the Burnham and Brennan Plan” or just “the Burnham Plan” for Edward P. Burnham’s more prominent contributions to it. The idea was to simplify the hodgepodge of identical and conflicting street names and house numbers, as well as to set up a process for giving names to new roads. What made the plan unique was its alphabetical road naming scheme for north/south streets starting with “A” at Lake Michigan and traveling west with successive letters.

Because most of the area around Gladstone Park developed after the Plan of Chicago was put into effect, the neighborhood was profoundly affected by the new road organizational guidelines.

First, since the neighborhood is in the Far Northwest section of the city, all streets in the area were set up with either a “north” or “west” designation. While people in newly-annexed towns may have groused about having to add a directional component to streets they once knew more simply as one word, they benefitted by the scheme that ordered the grid system in a very predictable way. Still, old ways had a hard time of dying and city dwellers still routinely drop the the directional prefix when interacting with others where they live, as in “Oh, I like the pizzeria at Milwaukee and Ardmore” not “the pizzeria at N(orth) Milwaukee and W(est) Ardmore.” The assumption is that your neighbors know exactly what you mean without having to bother with more formal designations.

But if one drops all the “N” and “W” directional prefixes in any kind of official capacity, such as filing a legal document or mailing a letter, there’s trouble. Nobody knows exactly which part of the city you mean. Which is why this website always clarifies Gladstone Park road names with “north” or “west” to distinguish them from same-sounding addresses found in southern and eastern parts of the city. This eliminates any possibility of confusing Northwest Side streets with their sister streets on Chicago’s Southside just because they have the same basic name.

Second, the new unifying grid system set house/lot numbers consecutively according to how far they were from the center city. Each regular long block of streets radiating out of the Loop, or ground zero, is made up of 100 numbers and rounded off as such. An address numbered 364, for example, is said to be in the “300 block;” one at 1364 in the “1300 block.” Eight blocks of 800 numbers constitute a mile. Odd numbers are found on the east sides of the streets, even numbers on the west. This scheme did more than give a house a numbered address; it also helped residents to locate any one address fairly precisely and know approximately how far away one is from another without having to consult a map.

When Chicago urban planners platted the streets on the North Side, it rejected the use of numbers for its westerly-traveling roadways such as those that preexisted in the south. So there’s nothing in the north like W. 35th Street that travels west from the Loop to White Sox Park or W. 55th Street that brings drivers into Hyde Park. All roadways traveling into the Far Northwest Side, including Gladstone Park have word names.

By the time planners made their way westward from Lake for their northerly-traveling streets, they had already gone through the A’s through N’s, so all new north/south streets in Gladstone Park’s start with “M;” house numbering in the community starts with the 5200 block at W. Foster and ends in the 6300s at the northern boundary at W. Devon. Today a full 21 of the community’s 30 north-south streets have names starting with M. Using the conventional city pattern of honoring famous people, there are streets named after railroad tycoon Charles Henry Markham (N. Markham), Mayor Roswell B. Mason (N. Mason), and theater owner James Hubert McVicker (N. McVicker). In recognition of nature, others roadways are named after flowers and trees, along with one named for a fruit tree (N. Mango).

Meanwhile, all north-south roads in Chicago had by the 1830s been designated with the “Avenue” suffix by surveyor James Thompson, according to the 1997 The Chicago Tribune article The Long and Winding Road by Mary Breslin. Thus, the great majority of roadways Gladstonians live and shop on are Avenues, not Streets, Lanes, or Drives. The only two exceptions to the north-south Avenue rule in Gladstone Park are N. Indian Road and N. Northwest Highway.

Even more so than its directional prefixes, Chicagoans tend to leave suffixes off when referring to their roadways. With “avenue” the default for so many of their streets, even some major corporations downtown will leave the suffix entirely off their letterheads, even if it’s not the fully-accepted (legal) USPS address. Fortunately, local postal workers have learned to handle it. Because there is no confusion about this local custom, this website leaves suffixes off “avenue” designations unless they appear to be necessary.

Knowing how the Chicago naming/numbering system works not only makes it easy to find the approximate location of a house or business in the immediate neighborhood, but also gives clues to where an address further away is. Invited out of the community to see your niece in a play at Smyser Elementary School at 4310 N. Melvina? Combining the alphabetical street name scheme with the numbering pattern, you automatically know it’s the equivalent of 9 long blocks or so south of Gladstone Park, probably across the border from Jefferson Park in the Portage Park neighborhood. Alphabetically, N. Melvina is somewhere between N. Meade and N. Merrimac, so that tells about how far west it is, too.