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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.
Many tourist attractions downtown are within walking distance of each other. If not, public transit (CTA) or taxis are an easy option. The CTA website - http://www.transitchicago.com/ and click on the trip planner link - is very easy to use. Check out the public transportation section of this site for further details.
Some tourist attractions are simply known for their name - not an address. For example, the John Hancock Center is at 875 N. Michigan Ave. Sears Tower is at 233 S. Wacker Drive. Illinois Center is at 111 E. Wacker. Water Tower Place is at 845 N. Michigan Ave. Navy Pier is at 600 E. Grand Ave.
One way to get to know the city is to have a local show you around, and the City of Chicago Dept. of Cultural Affairs has a service that does just that FOR FREE!
The Chicago Greeter program offers visitors (groups of up to 6) a chance to hook up with a local for a FREE tour of 25 neighborhoods, architectural attractions, hidden gems, or whatever special requests the visitor might have. The program even includes a FREE VISITORS PASS for use on the CTA's 'L' or Bus system! The program also offers an INSTAGREETER© option; this option allows visitors who didn't have time to make a reservation to meet up with a Chicago Greeter representative at the Chicago Cultural Center and spend an hour with them walking around the loop! It is a fantastic way for visitors and locals alike to discover the hidden gems of Chicago!
It’s very difficult to get lost in Chicago. Your hotel should be able to provide you with a map. Get out and explore. When in doubt, just ask. Have fun!