Chicago parking by block · Rogers Park · Ward 49

Parking at 7450 N Winchester Ave

Chicago sets parking rules by the block, so this covers 7400–7499 N Winchester Ave. Everything here is from City records — 31,771 parking tickets written across 103 blocks within a 10-minute walk, 2023–2025.

When is this block cleaned?

Monday, September 28

9am–2pm. A missed one is $60.

Do I need a permit?

Not in a residential permit zone.

Cameras nearby?

None

None within a 10-minute walk.

Every 2026 street-cleaning day on this block

Ward 49, section 4. The restriction runs 9am–2pm on each of these; a missed one is $60 and it doubles if it goes unpaid.

Apr

Wed

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Streets to watch near 7450 N Winchester Ave

street cleaning is the thing to watch around here: 7000 N Ravenswood Ave alone took 907 tickets in three years, a 10 min walk away.

Street cleaning11,813 tickets

Move the car on cleaning days — the restriction runs 9am to 2pm.

7000 N Ravenswood Ave — 907 tickets, 10 min walk SE
7700 N Marshfield — 392 tickets, 10 min walk NE
1600 W Sherwin Ave — 386 tickets, 9 min walk E

Plate checks3,331 tickets

Plates get checked here. Keep your registration and both plates current.

7300 N Damen Ave — 872 tickets, 2 min walk SW
2000 W Birchwood Ave — 510 tickets, 3 min walk W
7300 N Winchester Ave — 493 tickets, 2 min walk S

Posted restrictions7,412 tickets

Posted time restrictions. Worth reading the sign twice — this block is enforced.

2000 W Jarvis Ave — 1,607 tickets, 4 min walk SW
2000 W Fargo Ave — 612 tickets, 4 min walk W
7300 N Ashland Ave — 512 tickets, 9 min walk E

Metered blocks8,997 tickets

Metered. Pay the full time you will actually be gone, and set an alarm.

7100 N Clark St — 2,024 tickets, 8 min walk SE
7600 N Paulina St — 1,513 tickets, 7 min walk NE
1700 W Howard St — 1,273 tickets, 6 min walk NE

Other enforcement175 tickets

Enforced regularly. Read the posted signs before you park.

7200 N Rogers Ave — 175 tickets, 5 min walk S

How to not get any of these

A text the night before every cleaning day on this block.
Your city sticker and plates bought on time — a missed sticker is $200.
The tickets you still get contested by mail, where 59% are dismissed.

The average ticketed Chicago driver pays $319 a year in fines and late fees. Autopilot is $99/year.

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Ticket counts are parking citations issued 2023–2025 from City of Chicago records obtained under the Illinois Freedom of Information Act (5 ILCS 140), placed to the 100-block. Speed and red-light citations are counted separately. Street-cleaning dates are the City’s published 2026 season for ward 49, section 4. Schedules change — always follow the posted signs.