Watch this video about modes of transportation-pretty informative and pretty cool.
There are great ideas about how transportation works in Chicago.
Check out this reminder from TripAdvisor:
Chicago has one of the world’s simplest street patterns and numbering systems. Chicago streets are laid out in a simple grid system. The intersection of State & Madison is essentially Ground Zero in Chicago. In Chicago, there are 8 “standard” city blocks per mile. Although many blocks are further divided in half.
A standard block has 100 address numbers, meaning there are 800 numbers per mile. For example, 800 N. State St is eight blocks north of Madison on State St. 1900 W. Madison is nineteen blocks west of State St on Madison. There are some exceptions to the rule – such as streets that run on an angle – Milwaukee, Elston, Archer to name a few. On Chicago’s south side, the east-west streets are numbered. And those numbers correspond to the address numbers, in hundreds. For example, 87th Street is 8700 south. There actually were “errors” over the first 3 miles south of Madison Street, resulting in 12th Street, 22nd Street, and 31st Street being the first 3 “mile” streets south of Madison Street. South of 31st Street, there are 8 numbered streets per mile. 12th Street eventually became Roosevelt Road, while 22nd Street is now Cermak Road.
Addresses that end in an even number will be on the west or north sides of the street. Odd numbered addresses will be either on the east or south side of the street.
A good source for pdf versions of Chicago streets can be found here.