Chicago parking by block · Uptown

Parking at 550 W Wilson Dr

Chicago sets parking rules by the block, so this covers 500–599 W Wilson Dr. Everything here is from City records — 21,591 parking tickets written across 52 blocks within a 10-minute walk, 2023–2025.

When is this block cleaned?
Not published
No 2026 season is published for this section.
Do I need a permit?
No
Not in a residential permit zone.
Cameras nearby?
None
None within a 10-minute walk.

Streets to watch near 550 W Wilson Dr

street cleaning is the thing to watch around here: 800 W Lawrence Ave alone took 1,054 tickets in three years, a 9 min walk away.

Street cleaning8,137 tickets
Move the car on cleaning days — the restriction runs 9am to 2pm.
Permit zones942 tickets
Permit zone. You need a zone sticker or a day pass, whatever the hour.
Plate checks813 tickets
Plates get checked here. Keep your registration and both plates current.
Posted restrictions6,870 tickets
Posted time restrictions. Worth reading the sign twice — this block is enforced.
Metered blocks3,842 tickets
Metered. Pay the full time you will actually be gone, and set an alarm.
Other enforcement876 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. 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, 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

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