Parking at 250 S Winchester
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Parking at this address

250 S Winchester

Ward 27, cleaning section 5 · 44,880 parking tickets were written across 135 blocks within a 10-minute walk, 2023–2025.
When is this block cleaned?
Friday, October 2
Then Monday, October 5 · Monday, November 2 · Tuesday, November 3. 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
5 S Ashland Ave (10 min walk) · 1546 W Madison St (10 min walk)

Streets to watch nearby

street cleaning is the thing to watch around here: 2000 W Washington Blvd alone took 212 tickets in three years, a 7 min walk away.

Street cleaning754 tickets
Move the car on cleaning days — the restriction runs 9am to 2pm.
  • 2000 W Washington Blvd — 212, 7 min walk NW
  • 2100 W Washington Blvd — 173, 8 min walk NW
  • 100 S Bell Ave — 160, 8 min walk W
  • 1700 W Jackson Blvd — 136, 6 min walk E
  • 400 S Paulina St — 73, 7 min walk SE
Permit zones8,300 tickets
Permit zone. You need a zone sticker or a day pass, whatever the hour.
  • 1500 W Monroe St — 1,816, 10 min walk E
  • 1600 W Adams St — 1,253, 7 min walk E
  • 1600 W Warren Blvd — 1,197, 9 min walk NE
  • 1500 W Adams St — 1,107, 10 min walk E
  • 2000 W Warren Blvd — 488, 5 min walk NW
Plate checks10,403 tickets
Plates get checked here. Keep your registration and both plates current.
  • 2000 W Adams St — 410, 4 min walk W
  • 2200 W Warren Blvd — 370, 9 min walk NW
  • 100 S Wood St — 369, 4 min walk E
  • 2100 W Gladys — 363, 6 min walk SW
  • 2000 W Jackson Blvd — 361, 4 min walk SW
Posted restrictions3,585 tickets
Posted time restrictions. Worth reading the sign twice — this block is enforced.
  • 1600 W Congress Pkwy — 1,236, 9 min walk SE
  • 1700 W Congress Pkwy — 987, 7 min walk SE
  • 1600 W Jackson Blvd — 492, 8 min walk E
  • 2100 W Madison St — 393, 6 min walk NW
  • 1700 W Van Buren St — 296, 7 min walk SE
Metered blocks20,746 tickets
Metered. Pay the full time you will actually be gone, and set an alarm.
  • 1900 W Ogden Ave — 7,468, 8 min walk S
  • 1900 W Congress Pkwy — 2,909, 5 min walk S
  • 1800 W Harrison St — 2,398, 7 min walk SE
  • 600 S Wood St — 2,146, 9 min walk SE
  • 1800 W Congress Pkwy — 2,085, 5 min walk S

Every 2026 street-cleaning day on this block

Ward 27, section 5. Restriction runs 9am–2pm on each of these; a missed one is $60, and it doubles if it goes unpaid.

Apr13Mon
Apr14Tue
May11Mon
May12Tue
Jun9Tue
Jun10Wed
Jul9Thu
Jul10Fri
Aug6Thu
Aug7Fri
Sep3Thu
Sep4Fri
Oct2Fri
Oct5Mon
Nov2Mon
Nov3Tue

What makes this easy

✓
Street cleaning
A text the night before every cleaning day on this block — the next is Friday, October 2.
–
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.