Parking at 3750 S Winchester Ave
Chicago sets parking rules by the block, so this covers 3700–3799 S Winchester Ave. Everything here is from City records — 10,517 parking tickets written across 85 blocks within a 10-minute walk, 2023–2025.
Every 2026 street-cleaning day on this block
Ward 12, section 11. 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 3750 S Winchester Ave
street cleaning is the thing to watch around here: 1600 W 37th St alone took 286 tickets in three years, a 8 min walk away.
- 1600 W 37th St — 286 tickets, 8 min walk E
- 2200 W 37th St — 259 tickets, 10 min walk W
- 3600 S Paulina St — 217 tickets, 7 min walk E
- 1600 W 38th St — 415 tickets, 8 min walk E
- 3700 S Paulina St — 202 tickets, 6 min walk E
- 1900 W 34th Pl — 202 tickets, 10 min walk N
- 3600 S Marshfield Ave — 73 tickets, 8 min walk NE
- 3700 S Damen Ave — 48 tickets, 1 min walk W
- 1900 W Pershing Rd — 40 tickets, 3 min walk S
- 3700 S Wood St — 260 tickets, 4 min walk E
- 3500 S Paulina St — 203 tickets, 8 min walk NE
- 3500 S Hermitage Ave — 169 tickets, 8 min walk NE
- 1600 W 35th St — 222 tickets, 10 min walk NE
- 1700 W 37th St — 162 tickets, 6 min walk E
- 3500 S Honore St — 138 tickets, 6 min walk NE
- 2000 W 34th St — 69 tickets, 10 min walk N
Cameras within a 10-minute walk
- 2080 W Pershing Rd — speed camera, 5 min walk SW
How to not get any of these
- A text the night before every cleaning day on this block.
- A spoken warning before you reach any of the 1 cameras nearby.
- 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 12, section 11. Schedules change — always follow the posted signs.