Chicago parking by block · Austin · Ward 29

Parking at 5550 W Madison

Chicago sets parking rules by the block, so this covers 5500–5599 W Madison. Everything here is from City records — 24,094 parking tickets written across 117 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?

5816 W Jackson Blvd (8 min walk) · 5201 W Madison St (9 min walk)

Every 2026 street-cleaning day on this block

Ward 29, section 2. The restriction runs 9am–2pm on each of these; a missed one is $60 and it doubles if it goes unpaid.

Apr

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Streets to watch near 5550 W Madison

street cleaning is the thing to watch around here: 5500 W Jackson Blvd alone took 643 tickets in three years, a 5 min walk away.

Street cleaning10,323 tickets

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

5500 W Jackson Blvd — 643 tickets, 5 min walk S
0 N Waller — 509 tickets, 5 min walk NW
0 N Mayfield Ave — 471 tickets, 8 min walk W

Permit zones4,940 tickets

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

0 N Pine — 1,138 tickets, 2 min walk NE
0 N Long — 567 tickets, 5 min walk NE
5500 W Adams — 550 tickets, 3 min walk S

Plate checks5,463 tickets

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

300 N Pine — 657 tickets, 8 min walk N
100 N Parkside — 619 tickets, 5 min walk NW
0 N Parkside — 509 tickets, 3 min walk NW

Posted restrictions1,626 tickets

Posted time restrictions. Worth reading the sign twice — this block is enforced.

200 N Pine — 613 tickets, 7 min walk N
5500 W Fulton — 342 tickets, 8 min walk N
5400 W Fulton — 232 tickets, 8 min walk N

Other enforcement1,546 tickets

Enforced regularly. Read the posted signs before you park.

100 N Central — 607 tickets, 4 min walk N
5800 W Madison — 443 tickets, 8 min walk W
5400 W Madison — 221 tickets, 2 min walk E

Cameras within a 10-minute walk

5816 W Jackson Blvd — speed camera, 8 min walk SW
5201 W Madison St — red-light camera, 9 min walk E
506 S Central Ave — speed camera, 9 min walk S
515 S Central Ave — speed camera, 10 min walk S
5146 W Madison St — red-light camera, 10 min walk E

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 5 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 29, section 2. Schedules change — always follow the posted signs.