In Chicago all the streets are laid out in a grid pattern with corresponding numbers that start at State Street (running north south) and Madison (running east west). The address of that intersection is 0,0 or 0 State and 0 Madison. In Chicago 8 blocks equals a mile.* And major roads exist at half mile intervals for the most part.
For example, going north the numbers as they correspond to the major east west streets are:
Madison Ave., 0 N/S
Chicago Ave., 800 N
Division St., 1200 N
North Ave., 1600 N
Armitage Ave., 2000 N
Fullerton Ave., 2400 N
Diversy Ave., 2800 N
Belmont Ave., 3200 N
Addison Ave. 3600 N
Irving Park Ave., 4000 N
... and so on. By looking at the number and dividing by 8 (really 800 I suppose) you can tell that Fullerton is 3 miles north of Madison Avenue.
For north south streets it's:
State St., 0 E/W
Halsted Ave., 800 W
Sheffield Ave., 1000 W
Racine Ave., 1200 W
Southport Ave., 1400 W
Ashland Ave., 1600 W
Damen Ave., 2000 W
Western Ave., 2400 W
Here's a more complete list.
I used to live at 1034 west Belmont. Belmont is 3200 north, so I was 10.34 blocks west of State and 32 blocks north of Madison. If you understand how this works you can get anywhere with relative ease as long as you know the numbers of the place you're trying to find as numbers are on all Chicago street signs. As an added bonus you can figure out this distance if you feel compelled to do so as I often am.
One more odd note; even numbered addresses are on the west (on north south) and north side (on east west) of streets. Odd numbers are on the opposite. So again using the example of 1034 west Belmont you now know I lived at 1034 W, 3200 N, and on the north side of Belmont.
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This is the Lake Shore path. Its end points are Bryn Mawr Avenue (5600 N) on the north and 67th on the south. Bryn Mawr is 56/8 = 7 miles north of Madison and 67th is... Madison to 31st is 3 miles (see below*) plus 4.5 miles for the remaining 36 blocks giving us 14.5 miles in total... not bad considering the winding nature of the path. It's about 16.5 miles long according to Google Earth which has a distance and path function so you can track distances... yea I know; amazingly simple, useful, and utterly dorky.
*The exception to this is actually where I live now; south of Madison Avenue. Between Madison and Roosevelt 12 blocks equals a mile, between Roosevelt and 22nd/Cermak 10 blocks equals a mile, and between 22nd and 31st 9 blocks equals a mile. Thus, from Madison to 31st Street is 3 miles.
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