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

1. What are the northernmost, southernmost, easternmost and westernmost streets in Chicago? Answer.

2. Which street is the beginning of Illinois Highway 1, which ends at the Ohio River in Cave-in-Rock? Answer.

3. We have a Lincoln Avenue, but we also used to have a Lincoln Street. What is it called now? Answer.

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

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

6. How many streets are named after mayors of Chicago? Answer.

7. What place is the namesake of Devon Avenue? Answer.

8. What was the original name of the southern stretch of DuSable Lake Shore Drive? Answer.

9. Which school is the namesake of School Street? Answer.

10. Which street is named after the president who was sworn into office on the same day Chicago was incorporated as a city? Answer.

11. Western Avenue is the longest street in Chicago. What is the shortest? Answer.

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

13. There’s a neighborhood in North Lawndale known as K-Town, because all the street names begin with K: Kostner, Kolmar, Keeler, Kenneth, Karlov. Why? Answer.

14. Was there ever an island on Stony Island Avenue? Answer.

15. On Chicago’s grid system, there’s a major street every half mile. Which streets are 3600 north, south, east and west? Answer.

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

17. What are the current names of the streets originally designated 12th, 22nd and 55th? Answer.

18. DuSable Lake Shore Drive is not the first street named after the city’s founder, Jean Baptiste Point du Sable. What is? Answer.

19. There are five Western Avenue stops on the CTA’s ‘L’ system. Which four lines is it on, and on which line does it appear twice? Answer.

20. What is the first numbered street on the South Side? Answer.


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

2. Halsted Street

3. Wolcott Avenue

4. Broadway

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, that town is pronounced DEH-von, like the English county. The origin of Chicago’s pronunciation — Duh-VON — is a mystery.

8. Leif Ericson Drive

9. Hawthorne Scholastic Elementary, at the corner of Clifton and School

10. Van Buren Street

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

12. Ogden Avenue

13. In 1913, Chicago’s 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 that, streets west of Pulaski would begin with K, the 11th letter of the alphabet. The scheme was carried westward, through 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 Names, by 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 are now 92nd and 93rd Streets.”

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

16. Benjamin Rush, namesake of Rush Street.

17. Roosevelt Road, Cermak Road, Garfield Boulevard

18. Jean Avenue, in the Edgebrook neighborhood

19. Blue, Brown, Pink and Orange. It appears twice on the Blue line.

20. 8th Street