Parking at 5750 S Winchester Ave
Chicago sets parking rules by the block, so this covers 5700–5799 S Winchester Ave. Everything here is from City records — 8,440 parking tickets written across 105 blocks within a 10-minute walk, 2023–2025.
Every 2026 street-cleaning day on this block
Ward 15, section 9. The restriction runs 9am–2pm on each of these; a missed one is $60 and it doubles if it goes unpaid.
Streets to watch near 5750 S Winchester Ave
street cleaning is the thing to watch around here: 5600 S Wolcott Ave alone took 273 tickets in three years, a 3 min walk away.
- 5600 S Wolcott Ave — 273 tickets, 3 min walk NE
- 5700 S Claremont Ave — 201 tickets, 10 min walk W
- 5600 S Winchester Ave — 200 tickets, 3 min walk N
- 2100 W Garfield Blvd — 61 tickets, 8 min walk NW
- 5700 S Marshfield Ave — 193 tickets, 8 min walk E
- 5500 S Wood St — 186 tickets, 6 min walk NE
- 5900 S Paulina St — 175 tickets, 8 min walk SE
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.
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 15, section 9. Schedules change — always follow the posted signs.