Chicago parking by block · West Englewood · Ward 16

Parking at 5950 S Winchester Ave

Chicago sets parking rules by the block, so this covers 5900–5999 S Winchester Ave. Everything here is from City records — 7,366 parking tickets written across 93 blocks within a 10-minute walk, 2023–2025.

When is this block cleaned?
Monday, September 28
9am–2pm. A missed one is $60.
Do I need a permit?
No
Not in a residential permit zone.
Cameras nearby?
2
6274 S Damen Ave (9 min walk) · 6309 S Damen Ave (9 min walk)

Every 2026 street-cleaning day on this block

Ward 16, section 13. The restriction runs 9am–2pm on each of these; a missed one is $60 and it doubles if it goes unpaid.

May
5
Tue
May
6
Wed
Jul
17
Fri
Jul
20
Mon
Sep
28
Mon
Sep
29
Tue

Streets to watch near 5950 S Winchester Ave

street cleaning is the thing to watch around here: 5600 S Wolcott Ave alone took 273 tickets in three years, a 8 min walk away.

Street cleaning3,829 tickets
Move the car on cleaning days — the restriction runs 9am to 2pm.
Plate checks2,885 tickets
Plates get checked here. Keep your registration and both plates current.

Cameras within a 10-minute walk

  • 6274 S Damen Ave — red-light camera, 9 min walk S
  • 6309 S Damen Ave — red-light camera, 9 min walk S

How to not get any of these

  • A text the night before every cleaning day on this block.
  • A spoken warning before you reach any of the 2 cameras nearby.
  • Your city sticker and plates bought on time — a missed sticker is $200.
  • The tickets you still get contested by mail, where 59% are dismissed.
The average ticketed Chicago driver pays $319 a year in fines and late fees. Autopilot is $99/year.
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Ticket counts are parking citations issued 2023–2025 from City of Chicago records obtained under the Illinois Freedom of Information Act (5 ILCS 140), placed to the 100-block. Speed and red-light citations are counted separately. Street-cleaning dates are the City’s published 2026 season for ward 16, section 13. Schedules change — always follow the posted signs.