01/11/2015 Run 10.24 Miles. Here is a Spreadsheet of the list of Buildings and Attractions for CA # 43 South Shore:
And here is the link to the Map of South Shore:
https://www.mapmyrun.com/routes/view/599103454
03/06/2021 We ran 6.2 Miles passing by items 1 to 18:
Using this map:
03/13/2021 We ran 5.95 Miles passing by items 19 to 40.
… that will take you past all of the Buildings and Attractions included on the above spreadsheet.
1. Enrico Fermi Elementary School (S. Shore Fine Arts School). 1970’s ?
Building Mural kitty-corner from Enrico Fermi School.
2. Stony Island Trust & Savings Bank Building. 1923. William Gibbons Uffendell.
3. Parkside Public School. 1917. Aurthur F. Hussander.
4. Jackson Park Highlands Historic District. 2 houses on East 70th St. Probably after 1905.
5. Bryn Mawr Community Church. 1925.
6. Jeffery-Cyril Historic District. 1 of 6 Apartment Buildings. Paul F. Olsen. Spanish Colonial.
6. Jeffery-Cyril Historic District. 2 of 6 Apartment Buildings. Paul F. Olsen. Art Deco.
6. Jeffery-Cyril Historic District. 3 of 6 Apartment Buildings. Paul F. Olsen. Gothic.
6. Jeffery-Cyril Historic District. 4 of 6 Apartment Buildings. Paul F. Olsen. Georgian. South of the above building.
6. Jeffery-Cyril Historic District. 5 of 6 Apartment Buildings. Paul F. Olsen. Gothic.
6. Jeffery-Cyril Historic District. 6 of 6 Apartment Buildings. Paul F. Olsen. Gothic.
7. St. Philip Neri School. 1913-1914.
8. St. Philip Neri Church. 1926-1928. Joseph W. McCarthy. View to the Northeast.
8. St. Philip Neri Church. 1926-1928. Joseph W. McCarthy. Detail of Church entrance.
8. St. Philip Neri Church. 1926-1928. Joseph W. McCarthy. View to the Northwest.
9. Allan Miller House. 1913-1915. John Van Bergen.
10. Isabelle C. O’Keefe Elementary School. 1925-1936.
11. Shoreline Apartments. 1928. Henry K. Holsman. 
11. Shoreline Apartments. 1928. Henry K. Holsman. Detail, first 4 floors.
68th St. Pumping Station. One of 12 Pumping Stations in Chicago.
12. South Shore Country Club. 1905-1916. Marshall & Fox. Looking North towards entrance.
12. South Shore Country Club. 1905-1916. Marshall & Fox. Looking South towards back of Country Club.
12. South Shore Country Club. 1905-1916. Marshall & Fox. Looking North from back of Country Club towards downtown Chicago.
13. Robert A. Black North School & Synagogue. 1968.
14. South Shore Beach Apartments. 1927-1928. Robert S. DeGoyler.
15. 18th Church of Christ, Scientist. 1927-1931. Charles Draper Faulkner.
16. South Shore Public Library. 1929.
17. South Shore Community Church. 1900’s ?
18. Arthur Ashe Park. 1979. Renamed in 1993. Carol showing off her backhand !
19. The Lake-Side Terrace Apartments. 1922-1923. Eric Edwin Hall.
20. Adam Clayton Powell Jr. Elementary School. 2011.
21. Rainbow Beach Park. 1908.
22. Rainbow Beach Fieldhouse. 1999. David Woodhouse Architects.
Cheltenham Place & South Shore Dr. Great example of Stick Style Architecture.
23. St. Brides Church & School. 1907-1908.
24. Church of Sweden. 1906-1908.
25. Myra Bradwell School. 1926. Addition.
25. Myra Bradwell School. 1889. Original School.
26. South Shore Bungalow Historic District. 1911-1930. Storybook Style above, Brick Bungalow below.
28. Our Lady of Peace School 1926 Addition.
27. Our Lady of Peace Convent.
27. Our Lady of Peace Church. 1935. Joseph W. McCarthy.
27. Our Lady of Peace Church. 1935. Joseph W. McCarthy. Top – Coffered Ceiling and Altar. Bottom – Altar Detail.
27. Our Lady of Peace Church. 1935. Joseph W. McCarthy. East and West Transepts.
27. Our Lady of Peace Church. 1935. Joseph W. McCarthy. Balcony.
27. Our Lady of Peace Church. 1935. Joseph W. McCarthy. Top – 1922 School & Bell Tower and Bottom – 1926 School addition & Bell Tower.
27. Our Lady of Peace Church. 1935. Joseph W. McCarthy. Rectory.
29. South Shore International College Prep. H.S. 2011. Top – Looking North, Bottom – Looking South.
30. The South Side Hebrew Congregation. 1927-1928. Morris K. Komar.
31. Bryn Mawr Elem. School. 1893. Now Dr. Edward Alexander Bouchet International School.
32. South Shore United Methodist Church. 1920’s ?
34. South Shore High School. 1940.
35. Anton E. Hanson House. 1912. Perley Hale.
36. Jackson Park Hospital & Medical Center. 1917. Top – 1920 Original Entrance. Bottom – New Addition.
37. James Madison Elementary School. 1940’s ?
38. Saints Constantine & Helen Greek Orthodox Church. 1948-1952.
39. Muhammad U. of Islam & Clara Muhammad Elementary School. 1972 ?
40. Woodhull Park and Playground. 1927 Fieldhouse.
Chicago's 77 Community Areas 