Parking at 5250 W Winona St
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Parking at this address

5250 W Winona St

Ward 45, cleaning section 19 · 8,343 parking tickets were written across 119 blocks within a 10-minute walk, 2023–2025.
When is this block cleaned?
Wednesday, October 21
Then Thursday, October 22. 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?
3
5471 W Higgins Rd (9 min walk) · 5272 N Central Ave (10 min walk) · �5310 N Milwaukee Ave (10 min walk)

Streets to watch nearby

street cleaning is the thing to watch around here: 5300 W Foster Ave alone took 93 tickets in three years, a 2 min walk away.

Street cleaning607 tickets
Move the car on cleaning days — the restriction runs 9am to 2pm.
  • 5300 W Foster Ave — 93, 2 min walk NW
  • 5200 N Ludlam Ave — 79, 6 min walk NW
  • 5400 W Gale St — 79, 7 min walk SW
  • 5200 W Winona St — 63, 1 min walk E
  • 5200 N Lieb Ave — 59, 5 min walk NW
Permit zones1,243 tickets
Permit zone. You need a zone sticker or a day pass, whatever the hour.
  • 5500 W Edmunds St — 244, 9 min walk SW
  • 4900 N Lester Ave — 170, 7 min walk SW
  • 5100 W Strong St — 149, 6 min walk SE
  • 5100 N Lovejoy Ave — 130, 5 min walk W
  • 5100 W Ainslie St — 97, 7 min walk SE
City sticker checks133 tickets
They check stickers on this block. Keep your city sticker current.
  • 5200 N Laramie Ave — 50, 3 min walk NE
  • 5200 N Leclaire Ave — 42, 5 min walk NE
  • 5000 N Leclaire Ave — 41, 6 min walk SE
Plate checks2,790 tickets
Plates get checked here. Keep your registration and both plates current.
  • 5000 N Northwest Hwy — 255, 5 min walk SW
  • 5000 W Argyle St — 205, 7 min walk SE
  • 4800 N Linder Ave — 177, 10 min walk SW
  • 5500 W Higgins Ave — 156, 9 min walk SW
  • 5000 W Carmen Ave — 149, 7 min walk E
Posted restrictions44 tickets
Posted time restrictions. Worth reading the sign twice — this block is enforced.
  • 4900 N Laramie Ave — 44, 6 min walk S

Every 2026 street-cleaning day on this block

Ward 45, section 19. Restriction runs 9am–2pm on each of these; a missed one is $60, and it doubles if it goes unpaid.

May21Thu
May22Fri
Aug6Thu
Aug7Fri
Oct21Wed
Oct22Thu

What makes this easy

✓
Street cleaning
A text the night before every cleaning day on this block — the next is Wednesday, October 21.
–
Permit zone
Not needed here, but we flag the zones that start nearby.
✓
Cameras
3 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.