Chicago Streets Quiz – Chicago Magazine

Chicago has over 4,000 miles of streets. We have streets named after presidents, explorers, hardware salesmen, teachers, brewers, and even the last survivor of the Boston Tea Party (the long Kennison Avenue). According to a university study, our road network “exhibits the closest approximation to a single perfect grid” of any major city in the world, but the grid is often interrupted by diagonal streets that were once Native American trails. We have a street 24 miles long and another 127 feet long. How well do you know the streets of Chicago? See if you can answer these questions (scroll down the page for answers).

1. What are the most northerly, southerly, easterly and westerly streets in Chicago? Responnse.

2. What street is the start of Illinois Highway 1, which ends at the Ohio River at Cave-in-Rock? Responnse.

3. We have a Lincoln Avenue, but we also had a Lincoln Street. What is his name now? Responnse.

4. What is the only street without a suffix—that is, not designated street, avenue, boulevard, etc.? ? Responnse.

5. Which street is designated north, south, east and west? Responnse.

6. How many streets are named after Chicago mayors? Responnse.

7. What place is called Devon Avenue? Responnse.

8. What was the original name of the southern section of DuSable Lake Shore Drive? Responnse.

9. Which school is named after School Street? Responnse.

10. Which street is named after the president who was sworn in the same day Chicago was incorporated? Responnse.

11. Western Avenue is the longest street in Chicago. Which is the shortest? Responnse.

12. U.S. Route 66 began at the corner of Michigan and Jackson, but for most of its journey through Chicago it ran diagonally along this street. Responnse.

13. There is a neighborhood in North Lawndale known as K-Town, because all street names start with K: Kostner, Kolmar, Keeler, Kenneth, Karlov. Why? Responnse.

14. Has there ever been an island on Stony Island Avenue? Responnse.

15. On the Chicago network, there is a main street every half a mile. Which streets are 3600 north, south, east and west? Responnse.

16. 1980s pop ballad Richard Marx released an album named after a street named after a signer of the Declaration of Independence. Who was it? Responnse.

17. What are the current names of the streets originally designated 12and22n/a and 55and? Responnse.

18. DuSable Lake Shore Drive isn’t the first street named after the town’s founder, Jean Baptiste Point du Sable. What is? Responnse.

19. There are five Western Avenue stops on the CTA’s “L” system. On which four lines does it appear and on which line does it appear twice? Responnse.

20. What is the first numbered street on the south side? Responnse.


1. Juneway Terrace, 138and Street, State Line Road (also known as Avenue A), York Road

2. Halsted Street

3. Wolcott Avenue


5. Wacker Drive

6. Eleven: Busse Avenue (Fred A. Busse), Cermak Road (Anton Cermak), Cregier Avenue (DeWitt Clinton Cregier), Haines Street (John C. Haines), Heath Avenue (Monroe Heath), Mason Avenue (Roswell B. Mason), Medill Avenue (Joseph Medill), Ogden Avenue (William Ogden), Rice Street (John B. Rice), Rumsey Avenue (Julian S. Rumsey), Wentworth Avenue (John Wentworth).

7. Devon, Pennsylvania. However, this town is pronounced DEH-von, like the English county. The origin of the Chicago pronunciation – Duh-VON – is a mystery.

8. Leif Ericson Drive

9. Hawthorne Scholastic Elementary, corner of Clifton and School

10. Van Buren Street

11. WBEZ claims it’s McDermott Street, which has only eight points of address; however, the author of the Chicago History Today blog took actionand found that McDermott Street is 151.12 feet long, while Bay Court is 127.52 feet long.

12. Ogden Avenue

13. In 1913, the Chicago Planning Commission approved a street naming scheme based on the fact that Crawford Avenue (now Pulaski Road) is 11 miles west of the city’s eastern border. Because of this, streets west of Pulaski would start with K, 11and letter of the alphabet. The pattern was made westward, across L (12 miles), M (13 miles), N (14 miles), O (15 miles) and P (16 miles).

14. Sort of. According to the book Streetwise Chicago: A History of Chicago Street Namesby Don Hayner and Tom McNamee, “When all of Chicago was a lake, the limestone ridge along which this street runs protruded above the waterline between what is now 92n/a and 93rd Streets.”

15. Addison Street, 36and Street, Central Park Avenue and Ewing Avenue

16. Benjamin Rush, namesake of Rush Street.

17. Roosevelt Road, Cermak Road, Garfield Boulevard

18. Avenue Jean, in the Edgebrook neighborhood

19. Blue, brown, pink and orange. It appears twice on the blue line.

20. 8and Street

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