Parking at 1550 W 99th St
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Parking at this address

1550 W 99th St

Ward 19, cleaning section 4 · 3,049 parking tickets were written across 68 blocks within a 10-minute walk, 2023–2025.
When is this block cleaned?
Friday, November 13
Then Monday, November 16. 9am–2pm. A missed one is $60.
Do I need a permit?
No
Not in a residential permit zone — but nearby blocks are, so a guest can still cross the line into one.
Cameras nearby?
2
1732 W 99th St (5 min walk) · 1601 W 95th St (10 min walk)

Streets to watch nearby

permit zones is the thing to watch around here: 9800 S Walden Pkwy alone took 73 tickets in three years, a 6 min walk away.

Permit zones128 tickets
Permit zone. You need a zone sticker or a day pass, whatever the hour.
  • 9800 S Walden Pkwy — 73, 6 min walk W
  • 9700 S Vanderpoel Ave — 55, 5 min walk NW
Plate checks1,539 tickets
Plates get checked here. Keep your registration and both plates current.
  • 1300 W 98th St — 157, 7 min walk E
  • 9900 S Charles St — 149, 3 min walk SE
  • 1300 W 97th Pl — 145, 7 min walk NE
  • 9900 S Winston Ave — 111, 6 min walk SE
  • 9700 S Charles St — 104, 4 min walk N
Posted restrictions48 tickets
Posted time restrictions. Worth reading the sign twice — this block is enforced.
  • 9900 S Walden Pkwy — 48, 6 min walk W
Metered blocks535 tickets
Metered. Pay the full time you will actually be gone, and set an alarm.
  • 9500 S Vanderpoel Ave — 313, 9 min walk NW
  • 9500 S Wood St — 222, 9 min walk NW
Other enforcement68 tickets
Enforced regularly. Read the posted signs before you park.
  • 1600 W 95th Street — 68, 10 min walk N

Every 2026 street-cleaning day on this block

Ward 19, section 4. Restriction runs 9am–2pm on each of these; a missed one is $60, and it doubles if it goes unpaid.

Apr9Thu
Apr10Fri
Jun22Mon
Jun23Tue
Sep1Tue
Sep2Wed
Nov13Fri
Nov16Mon

What makes this easy

✓
Street cleaning
A text the night before every cleaning day on this block — the next is Friday, November 13.
–
Permit zone
Not needed here, but we flag the zones that start nearby.
✓
Cameras
2 within a short walk. The app warns you out loud before you reach one.
✓
City sticker & plates
A missed sticker is $200 and it’s a deadline, not a driving mistake. We buy them on time, every year.
✓
The tickets you still get
Contested by mail — 59% of mailed contests are dismissed — and paid before the fine doubles.
✓
What it costs
The average ticketed Chicago driver pays $319 a year in fines and late fees. Autopilot is $99/year.