Parking at 5250 N Winthrop Ave
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Parking at this address

5250 N Winthrop Ave

Ward 48, cleaning section 7 · 55,550 parking tickets were written across 112 blocks within a 10-minute walk, 2023–2025.
When is this block cleaned?
Thursday, September 24
Then Friday, September 25 · Friday, October 23 · Monday, October 26. 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?
4
5147 N Broadway St (3 min walk) · 1211 W Foster Ave (3 min walk) · 5204 N Sheridan Rd (4 min walk) +1 more

Streets to watch nearby

street cleaning is the thing to watch around here: 1000 W Winona St alone took 743 tickets in three years, a 4 min walk away.

Street cleaning9,198 tickets
Move the car on cleaning days — the restriction runs 9am to 2pm.
  • 1000 W Winona St — 743, 4 min walk S
  • 5200 N Winthrop Ave — 567, 1 min walk S
  • 5200 N Kenmore Ave — 539, 2 min walk E
  • 5300 N Winthrop Ave — 466, 2 min walk N
  • 1000 W Berwyn Ave — 417, 2 min walk E
Permit zones786 tickets
Permit zone. You need a zone sticker or a day pass, whatever the hour.
  • 1000 W Ainslie St — 786, 9 min walk S
Plate checks6,674 tickets
Plates get checked here. Keep your registration and both plates current.
  • 5400 N Kenmore Ave — 854, 5 min walk N
  • 900 W Winona St — 746, 5 min walk SE
  • 5400 N Winthrop Ave — 661, 4 min walk N
  • 5300 N Kenmore Ave — 544, 3 min walk NE
  • 900 W Carmen Ave — 466, 6 min walk SE
Posted restrictions4,743 tickets
Posted time restrictions. Worth reading the sign twice — this block is enforced.
  • 1000 W Catalpa — 1,022, 6 min walk N
  • 5200 N Sheridan Road — 847, 3 min walk E
  • 5100 N Simonds Dr — 810, 9 min walk E
  • 1000 W Balmoral Ave — 594, 4 min walk NE
  • 1200 W Carmen Ave — 418, 6 min walk SW
Metered blocks34,029 tickets
Metered. Pay the full time you will actually be gone, and set an alarm.
  • 5000 N Sheridan Rd — 4,090, 5 min walk SE
  • 1000 W Argyle St — 2,328, 6 min walk S
  • 4900 N Sheridan Rd — 1,920, 8 min walk SE
  • 1000 W Bryn Mawr Ave — 1,865, 8 min walk N
  • 5500 N Broadway St — 1,643, 7 min walk N

Every 2026 street-cleaning day on this block

Ward 48, section 7. Restriction runs 9am–2pm on each of these; a missed one is $60, and it doubles if it goes unpaid.

Apr3Fri
Apr6Mon
May1Fri
May4Mon
Jun1Mon
Jun2Tue
Jun30Tue
Jul1Wed
Jul29Wed
Jul30Thu
Aug26Wed
Aug27Thu
Sep24Thu
Sep25Fri
Oct23Fri
Oct26Mon

What makes this easy

✓
Street cleaning
A text the night before every cleaning day on this block — the next is Thursday, September 24.
–
Permit zone
Not needed here, but we flag the zones that start nearby.
✓
Cameras
4 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.