Parking at 5450 S Winchester Ave
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Parking at this address

5450 S Winchester Ave

Ward 16, cleaning section 2 · 11,224 parking tickets were written across 126 blocks within a 10-minute walk, 2023–2025.
When is this block cleaned?
Friday, November 6
Then Monday, November 9. 9am–2pm. A missed one is $60.
Do I need a permit?
No
Not in a residential permit zone — but nearby blocks are, so a guest can still cross the line into one.
Cameras nearby?
None
No speed or red-light camera within a 10-minute walk.

Streets to watch nearby

street cleaning is the thing to watch around here: 5600 S Wolcott Ave alone took 273 tickets in three years, a 4 min walk away.

Street cleaning6,034 tickets
Move the car on cleaning days — the restriction runs 9am to 2pm.
  • 5600 S Wolcott Ave — 273, 4 min walk S
  • 1900 W 51st St — 269, 10 min walk N
  • 2100 W 51st St — 268, 10 min walk NW
  • 2000 W 51st St — 234, 10 min walk N
  • 5600 S Winchester Ave — 200, 4 min walk S
Permit zones68 tickets
Permit zone. You need a zone sticker or a day pass, whatever the hour.
  • 5500 S Claremont Ave — 68, 9 min walk W
City sticker checks61 tickets
They check stickers on this block. Keep your city sticker current.
  • 2100 W Garfield Blvd — 61, 6 min walk W
Plate checks4,344 tickets
Plates get checked here. Keep your registration and both plates current.
  • 2300 W 56th St — 274, 9 min walk W
  • 5200 S Marshfield Ave — 199, 10 min walk NE
  • 5500 S Wood St — 186, 4 min walk E
  • 5300 S Wood St — 185, 5 min walk NE
  • 5300 S Honore St — 174, 4 min walk NE

Every 2026 street-cleaning day on this block

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

Apr3Fri
Apr6Mon
Jun15Mon
Jun16Tue
Aug26Wed
Aug27Thu
Nov6Fri
Nov9Mon

What makes this easy

✓
Street cleaning
A text the night before every cleaning day on this block — the next is Friday, November 6.
–
Permit zone
Not needed here, but we flag the zones that start nearby.
–
Cameras
None nearby, but the app warns you anywhere in the city.
✓
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.