Chicago parking by block · Washington Heights · Ward 21

Parking at 9950 S May

Chicago sets parking rules by the block, so this covers 9900–9999 S May. Everything here is from City records — 4,792 parking tickets written across 91 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?
No
Not in a residential permit zone.
Cameras nearby?
2
813 W 99th St (9 min walk) · 9901 S Halsted St (9 min walk)

Every 2026 street-cleaning day on this block

Ward 21, 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
2
Thu
Jul
6
Mon
Aug
28
Fri
Aug
31
Mon
Oct
27
Tue
Oct
28
Wed

Streets to watch near 9950 S May

street cleaning is the thing to watch around here: 10200 S Sangamon St alone took 82 tickets in three years, a 9 min walk away.

Street cleaning206 tickets
Move the car on cleaning days — the restriction runs 9am to 2pm.
Plate checks3,802 tickets
Plates get checked here. Keep your registration and both plates current.

Cameras within a 10-minute walk

  • 813 W 99th St — red-light camera, 9 min walk E
  • 9901 S Halsted St — red-light camera, 9 min walk E

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 isn’t a permit zone, but several nearby are.
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Cameras you’re about to drive past
It says them out loud before you reach one — there are 2 within a short walk of here.
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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 Washington Heights 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 21, section 13. Schedules change — always follow the posted signs.