Chicago parking by block · Portage Park · Ward 45

Parking at 5250 W Windsor Ave

Chicago sets parking rules by the block, so this covers 5200–5299 W Windsor Ave. Everything here is from City records — 12,646 parking tickets written across 133 blocks within a 10-minute walk, 2023–2025.

When is this block cleaned?
Wednesday, September 16
9am–2pm. A missed one is $60.
Do I need a permit?
No
Not in a residential permit zone.
Cameras nearby?
4
5040 W Montrose Ave (5 min walk) · 4361 N Milwaukee Ave (5 min walk)

Every 2026 street-cleaning day on this block

Ward 45, section 7. The restriction runs 9am–2pm on each of these; a missed one is $60 and it doubles if it goes unpaid.

Apr
17
Fri
Apr
20
Mon
Jul
2
Thu
Jul
6
Mon
Sep
16
Wed
Sep
17
Thu

Streets to watch near 5250 W Windsor Ave

street cleaning is the thing to watch around here: 5200 W Hutchinson St alone took 118 tickets in three years, a 7 min walk away.

Street cleaning1,384 tickets
Move the car on cleaning days — the restriction runs 9am to 2pm.
Permit zones1,115 tickets
Permit zone. You need a zone sticker or a day pass, whatever the hour.
Plate checks4,598 tickets
Plates get checked here. Keep your registration and both plates current.
Posted restrictions1,505 tickets
Rush-hour restrictions. Read the sign before you leave it at 4pm.
Metered blocks3,186 tickets
Metered. Pay the full time you will actually be gone, and set an alarm.

Cameras within a 10-minute walk

  • 5040 W Montrose Ave — red-light camera, 5 min walk SE
  • 4361 N Milwaukee Ave — red-light camera, 5 min walk SE
  • 4949 W Lawrence Ave — speed camera, 8 min walk NE
  • 5432 W Lawrence Ave — speed camera, 9 min walk NW

How to not get any of these

  • A text the night before every cleaning day on this block.
  • A spoken warning before you reach any of the 4 cameras nearby.
  • 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 45, section 7. Schedules change — always follow the posted signs.