Chicago parking by block · Austin · Ward 29

Parking at 5250 W Gladys

Chicago sets parking rules by the block, so this covers 5200–5299 W Gladys. Everything here is from City records — 20,179 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?
No
Not in a residential permit zone.
Cameras nearby?
4
5201 W Madison St (6 min walk) · 5146 W Madison St (7 min walk)

Every 2026 street-cleaning day on this block

Ward 29, 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
15
Fri
May
18
Mon
Jun
26
Fri
Jun
29
Mon
Aug
6
Thu
Aug
7
Fri
Sep
16
Wed
Sep
17
Thu
Oct
27
Tue
Oct
28
Wed

Streets to watch near 5250 W Gladys

street cleaning is the thing to watch around here: 5000 W Monroe St alone took 695 tickets in three years, a 7 min walk away.

Street cleaning9,249 tickets
Move the car on cleaning days — the restriction runs 9am to 2pm.
Permit zones4,389 tickets
Permit zone. You need a zone sticker or a day pass, whatever the hour.
Plate checks5,269 tickets
Plates get checked here. Keep your registration and both plates current.
Posted restrictions335 tickets
Posted time restrictions. Worth reading the sign twice — this block is enforced.
Other enforcement544 tickets
Enforced regularly. Read the posted signs before you park.

Cameras within a 10-minute walk

  • 5201 W Madison St — red-light camera, 6 min walk N
  • 5146 W Madison St — red-light camera, 7 min walk N
  • 515 S Central Ave — speed camera, 9 min walk W
  • 506 S Central Ave — speed camera, 9 min walk W

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 4 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

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