Chicago parking by block · Logan Square · Ward 32

Parking at 2050 W Cortland St

Chicago sets parking rules by the block, so this covers 2000–2099 W Cortland St. Everything here is from City records — 72,257 parking tickets written across 156 blocks within a 10-minute walk, 2023–2025.

When is this block cleaned?
Not published
No 2026 season is published for this section.
Do I need a permit?
No
Not in a residential permit zone.
Cameras nearby?
None
None within a 10-minute walk.

Every 2026 street-cleaning day on this block

Ward 32, section 17. The restriction runs 9am–2pm on each of these; a missed one is $60 and it doubles if it goes unpaid.

May
1
Fri
May
4
Mon
Jun
30
Tue
Jul
1
Wed
Aug
26
Wed
Aug
27
Thu
Oct
23
Fri
Oct
26
Mon

Streets to watch near 2050 W Cortland St

street cleaning is the thing to watch around here: 2000 W Pierce Ave alone took 706 tickets in three years, a 10 min walk away.

Street cleaning4,466 tickets
Move the car on cleaning days — the restriction runs 9am to 2pm.
Permit zones8,137 tickets
Permit zone. You need a zone sticker or a day pass, whatever the hour.
Plate checks15,204 tickets
Plates get checked here. Keep your registration and both plates current.
Posted restrictions707 tickets
Rush-hour restrictions. Read the sign before you leave it at 4pm.
Metered blocks43,363 tickets
Metered. Pay the full time you will actually be gone, and set an alarm.
Other enforcement288 tickets
Enforced regularly. Read the posted signs before you park.

Get warned before it happens

Everything on this page is a deadline or a line on a map. Autopilot America watches both for you — it knows where you parked, and it tells you before the ticket exists.

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Street cleaning on this blockFree
A text the night before every cleaning day here. Free, no account needed →
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Parking restrictions where you leave the car
The app spots where you parked and checks it: temporary no-parking, permit zones, snow routes, meter time limits. This block isn’t a permit zone, but several nearby are.
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Cameras you’re about to drive past
It says them out loud before you reach one, anywhere in the city.
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Your city sticker and plates, on time
Both are deadlines, not driving mistakes. We remind you before each one lapses, with a direct link to renew, so the $200 sticker ticket doesn't catch you out.
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Late fees, handled
A Chicago ticket doubles 25 days after it’s issued. We pay the ones you owe before that clock runs out — and if a ticket doubles on our watch during your paid year, you get the year back.
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The tickets you still get, contested
By mail, where 59% of contested tickets are dismissed, with the City’s own evidence pulled under FOIA.
The average ticketed Chicago driver pays $319 a year in fines and late fees. Autopilot is $10/month or $99/year.
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Street-cleaning alerts are free and don’t need the app. The app — parking detection, restriction checks and camera warnings — comes with Autopilot Pro.

More on this block

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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 32, section 17. Schedules change — always follow the posted signs.