Chicago parking by block · New City · Ward 16

Parking at 5150 S Winchester Ave

Chicago sets parking rules by the block, so this covers 5100–5199 S Winchester Ave. Everything here is from City records — 18,605 parking tickets written across 116 blocks within a 10-minute walk, 2023–2025.

When is this block cleaned?

Friday, November 6

9am–2pm. A missed one is $60.

Do I need a permit?

Not in a residential permit zone.

Cameras nearby?

None

None within a 10-minute walk.

Every 2026 street-cleaning day on this block

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

Apr

Fri

Apr

Mon

Jun

Mon

Jun

Tue

Aug

Wed

Aug

Thu

Nov

Fri

Nov

Mon

Streets to watch near 5150 S Winchester Ave

street cleaning is the thing to watch around here: 4800 S Wood St alone took 553 tickets in three years, a 8 min walk away.

Street cleaning8,243 tickets

Move the car on cleaning days — the restriction runs 9am to 2pm.

4800 S Wood St — 553 tickets, 8 min walk NE
4700 S Wolcott Ave — 550 tickets, 10 min walk N
5000 S Damen Ave — 378 tickets, 2 min walk NW

Permit zones634 tickets

Permit zone. You need a zone sticker or a day pass, whatever the hour.

2200 W 50th Pl — 386 tickets, 9 min walk W
4800 S Hoyne Ave — 248 tickets, 8 min walk NW

Plate checks5,001 tickets

Plates get checked here. Keep your registration and both plates current.

4800 S Honore St — 389 tickets, 8 min walk N
4800 S Paulina St — 293 tickets, 10 min walk NE
1800 W 50th St — 221 tickets, 4 min walk NE

Posted restrictions3,698 tickets

Posted time restrictions. Worth reading the sign twice — this block is enforced.

4900 S Wood St — 557 tickets, 6 min walk NE
4900 S Winchester Ave — 542 tickets, 5 min walk N
4900 S Wolcott Ave — 538 tickets, 5 min walk N

Other enforcement685 tickets

Enforced regularly. Read the posted signs before you park.

4800 S Damen Ave — 685 tickets, 8 min walk N

How to not get any of these

A text the night before every cleaning day on this block.
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 2. Schedules change — always follow the posted signs.