Chicago parking by block · New City · Ward 15

Parking at 4950 S Winchester Ave

Chicago sets parking rules by the block, so this covers 4900–4999 S Winchester Ave. Everything here is from City records — 37,683 parking tickets written across 112 blocks within a 10-minute walk, 2023–2025.

When is this block cleaned?
Wednesday, October 28
9am–2pm. A missed one is $60.
Do I need a permit?
Zone 2399
A visitor without a day pass is a $75 ticket.
Cameras nearby?
None
None within a 10-minute walk.

Every 2026 street-cleaning day on this block

Ward 15, section 3. The restriction runs 9am–2pm on each of these; a missed one is $60 and it doubles if it goes unpaid.

Apr
7
Tue
Apr
8
Wed
May
5
Tue
May
6
Wed
Jun
3
Wed
Jun
4
Thu
Jul
2
Thu
Jul
6
Mon
Jul
31
Fri
Aug
3
Mon
Aug
28
Fri
Aug
31
Mon
Sep
28
Mon
Sep
29
Tue
Oct
27
Tue
Oct
28
Wed

Streets to watch near 4950 S Winchester Ave

street cleaning is the thing to watch around here: 4700 S Damen Ave alone took 559 tickets in three years, a 5 min walk away.

Street cleaning7,626 tickets
Move the car on cleaning days — the restriction runs 9am to 2pm.
Permit zones2,311 tickets
Permit zone. You need a zone sticker or a day pass, whatever the hour.
Plate checks3,642 tickets
Plates get checked here. Keep your registration and both plates current.
Posted restrictions4,042 tickets
Posted time restrictions. Worth reading the sign twice — this block is enforced.
Metered blocks19,040 tickets
Metered. Pay the full time you will actually be gone, and set an alarm.
Other enforcement840 tickets
Enforced regularly. Read the posted signs before you park.

Get warned before it happens

Everything on this page is a deadline or a line on a map. Autopilot America watches both for you — it knows where you parked, and it tells you before the ticket exists.

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Street cleaning on this blockFree
A text the night before every cleaning day here — the next is Wednesday, October 28. Free, no account needed →
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Parking restrictions where you leave the car
The app spots where you parked and checks it: temporary no-parking, permit zones, snow routes, meter time limits. This block is permit zone 2399, so a guest on the wrong side of that line is a $75 ticket.
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Cameras you’re about to drive past
It says them out loud before you reach one, anywhere in the city.
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Your city sticker and plates, on time
Both are deadlines, not driving mistakes. We remind you before each one lapses, with a direct link to renew, so the $200 sticker ticket doesn't catch you out.
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Late fees, handled
A Chicago ticket doubles 25 days after it’s issued. We pay the ones you owe before that clock runs out — and if a ticket doubles on our watch during your paid year, you get the year back.
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The tickets you still get, contested
By mail, where 59% of contested tickets are dismissed, with the City’s own evidence pulled under FOIA.
The average ticketed Chicago driver pays $319 a year in fines and late fees. Autopilot is $10/month or $99/year.
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Street-cleaning alerts are free and don’t need the app. The app — parking detection, restriction checks and camera warnings — comes with Autopilot Pro.

More on this block

Check another addressAll New City blocks

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 15, section 3. Schedules change — always follow the posted signs.