Chicago parking by block · Portage Park · Ward 45

Parking at 5550 W Windsor Ave

Chicago sets parking rules by the block, so this covers 5500–5599 W Windsor Ave. Everything here is from City records — 11,313 parking tickets written across 137 blocks within a 10-minute walk, 2023–2025.

When is this block cleaned?

Monday, September 14

9am–2pm. A missed one is $60.

Do I need a permit?

Not in a residential permit zone.

Cameras nearby?

5432 W Lawrence Ave (7 min walk) · 5471 W Higgins Rd (9 min walk)

Every 2026 street-cleaning day on this block

Ward 45, section 6. The restriction runs 9am–2pm on each of these; a missed one is $60 and it doubles if it goes unpaid.

Apr

Wed

Apr

Thu

Jun

Tue

Jul

Wed

Sep

Mon

Sep

Tue

Streets to watch near 5550 W Windsor Ave

street cleaning is the thing to watch around here: 5400 W Berteau Ave alone took 171 tickets in three years, a 9 min walk away.

Street cleaning1,871 tickets

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

5400 W Berteau Ave — 171 tickets, 9 min walk S
5900 W Eastwood Ave — 131 tickets, 10 min walk W
5800 W Eastwood Ave — 113 tickets, 8 min walk W

Permit zones105 tickets

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

4600 N Laramie Ave — 54 tickets, 10 min walk E
4700 N Linder Ave — 51 tickets, 6 min walk N

City sticker checks54 tickets

They check stickers on this block. Keep your city sticker current.

5600 W Grover St — 54 tickets, 10 min walk N

Plate checks4,769 tickets

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

5200 W Agatite Ave — 179 tickets, 8 min walk E
4800 N Linder Ave — 177 tickets, 8 min walk N
5500 W Agatite Ave — 166 tickets, 3 min walk S

Posted restrictions772 tickets

Rush-hour restrictions. Read the sign before you leave it at 4pm.

5200 W Montrose Ave — 270 tickets, 9 min walk SE
5400 W Montrose Ave — 216 tickets, 5 min walk SE
5300 W Montrose Ave — 182 tickets, 7 min walk SE

Metered blocks2,921 tickets

Metered. Pay the full time you will actually be gone, and set an alarm.

5300 W Veterans Pl — 691 tickets, 9 min walk NE
4700 N Milwaukee Ave — 500 tickets, 8 min walk NE
4600 N Milwaukee Ave — 449 tickets, 9 min walk E

Cameras within a 10-minute walk

5432 W Lawrence Ave — speed camera, 7 min walk NE
5471 W Higgins Rd — speed camera, 9 min walk N

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 2 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 6. Schedules change — always follow the posted signs.