Parking at 4250 N Winchester Ave
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Parking at this address

4250 N Winchester Ave

Ward 47, cleaning section 9 · 31,458 parking tickets were written across 141 blocks within a 10-minute walk, 2023–2025.
When is this block cleaned?
Thursday, October 15
Then Friday, October 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
4432 N Lincoln Ave (8 min walk) · 4118 N Ashland Ave (10 min walk)

Streets to watch nearby

street cleaning is the thing to watch around here: 4400 N Ashland Ave alone took 797 tickets in three years, a 10 min walk away.

Street cleaning9,397 tickets
Move the car on cleaning days — the restriction runs 9am to 2pm.
  • 4400 N Ashland Ave — 797, 10 min walk NE
  • 4100 N Ashland Ave — 510, 10 min walk E
  • 4200 N Ashland Ave — 441, 9 min walk E
  • 4300 N Ashland Ave — 360, 9 min walk E
  • 4400 N Winchester Ave — 306, 5 min walk N
Permit zones3,311 tickets
Permit zone. You need a zone sticker or a day pass, whatever the hour.
  • 4600 N Winchester Ave — 502, 10 min walk N
  • 4600 N Wolcott Ave — 434, 10 min walk N
  • 4000 N Hermitage Ave — 393, 8 min walk SE
  • 1800 W Cuyler Ave — 336, 6 min walk SE
  • 1800 W Larchmont Ave — 238, 9 min walk S
City sticker checks157 tickets
They check stickers on this block. Keep your city sticker current.
  • 4400 N Lincoln — 157, 8 min walk NW
Plate checks4,274 tickets
Plates get checked here. Keep your registration and both plates current.
  • 4000 N Ravenswood Ave — 267, 7 min walk SE
  • 4400 N Damen Ave — 249, 4 min walk N
  • 4600 N Seeley Ave — 227, 9 min walk N
  • 4300 N Ravenswood Ave — 210, 4 min walk NE
  • 4000 N Paulina St — 209, 9 min walk SE
Posted restrictions804 tickets
Posted time restrictions. Worth reading the sign twice — this block is enforced.
  • 1900 W Sunnyside Ave — 316, 6 min walk N
  • 4300 N Paulina St — 272, 8 min walk E
  • 1800 W Wilson Ave — 133, 8 min walk N
  • 4300 N Honore St — 83, 3 min walk NE

Every 2026 street-cleaning day on this block

Ward 47, section 9. Restriction runs 9am–2pm on each of these; a missed one is $60, and it doubles if it goes unpaid.

Apr23Thu
Apr24Fri
Jun22Mon
Jun23Tue
Aug18Tue
Aug19Wed
Oct15Thu
Oct16Fri

What makes this easy

✓
Street cleaning
A text the night before every cleaning day on this block — the next is Thursday, October 15.
–
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.