Parking at 9950 S Winchester Ave
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Parking at this address

9950 S Winchester Ave

Ward 19, cleaning section 5 · 3,467 parking tickets were written across 73 blocks within a 10-minute walk, 2023–2025.
When is this block cleaned?
Tuesday, November 17
Then Wednesday, November 18. 9am–2pm. A missed one is $60.
Do I need a permit?
Yes
Residential permit zone 12. A visitor without a day pass is a $75 ticket.
Cameras nearby?
1
1732 W 99th St (5 min walk)

Streets to watch nearby

permit zones is the thing to watch around here: 10300 S Hale Ave alone took 268 tickets in three years, a 10 min walk away.

Permit zones436 tickets
Permit zone. You need a zone sticker or a day pass, whatever the hour.
  • 10300 S Hale Ave — 268, 10 min walk S
  • 9800 S Walden Pkwy — 73, 5 min walk NE
  • 9700 S Vanderpoel Ave — 55, 8 min walk NE
  • 9800 S Damen Ave — 40, 4 min walk N
Plate checks136 tickets
Plates get checked here. Keep your registration and both plates current.
  • 9800 S Charles St — 94, 10 min walk E
  • 9700 S Hamilton Ave — 42, 8 min walk NW
Posted restrictions214 tickets
Posted time restrictions. Worth reading the sign twice — this block is enforced.
  • 10200 S Walden Pkwy — 166, 7 min walk S
  • 9900 S Walden Pkwy — 48, 3 min walk E
Metered blocks1,813 tickets
Metered. Pay the full time you will actually be gone, and set an alarm.
  • 1900 W 103rd St — 903, 8 min walk S
  • 1800 W 103rd St — 457, 8 min walk S
  • 10300 S Walden Pkwy — 453, 9 min walk S

Every 2026 street-cleaning day on this block

Ward 19, section 5. Restriction runs 9am–2pm on each of these; a missed one is $60, and it doubles if it goes unpaid.

Apr13Mon
Apr14Tue
Jun24Wed
Jun25Thu
Sep3Thu
Sep4Fri
Nov17Tue
Nov18Wed

What makes this easy

✓
Street cleaning
A text the night before every cleaning day on this block — the next is Tuesday, November 17.
✓
Permit zone
This block needs a zone permit; we flag the rules so a guest doesn’t collect a $75 ticket.
✓
Cameras
1 within a short walk. The app warns you out loud before you reach one.
✓
City sticker & plates
A missed sticker is $200 and it’s a deadline, not a driving mistake. We buy them on time, every year.
✓
The tickets you still get
Contested by mail — 59% of mailed contests are dismissed — and paid before the fine doubles.
✓
What it costs
The average ticketed Chicago driver pays $319 a year in fines and late fees. Autopilot is $99/year.