Parking struggles are a universal urban frustration, but some cities are in a league of their own. From sky-high rates to confusing rules and limited availability, these metros test even the most experienced drivers. Whether you’re relocating, commuting, or just planning a visit, knowing what to expect—and how to prepare—can save you time, money, and a potential citation.

Here are the top 10 U.S. cities with the worst parking, based on congestion, cost, enforcement, and availability—plus smart tips for parking smarter in each one.

1. New York City, NY
   Between alternate side rules, metered chaos, and limited space, NYC tops almost every parking pain index.
   How to beat it: Use apps like ParkMobile or SpotHero to book garages in advance, and always check NYC DOT regulations before parking on the street.
2. San Francisco, CA
   Extremely high hourly rates, aggressive enforcement, and hilly streets make SF a challenge.
   How to beat it: Check dynamic pricing through SFMTA, use SpotAngels to find real-time open spots, and avoid peak hours near popular districts like Mission and North Beach.
3. Boston, MA
   With old street layouts and minimal public garages, Boston’s downtown is difficult to navigate and even harder to park in.
   How to beat it: Consider parking further out and taking the MBTA into the city. Use ParkWhiz for game-day and event reservations.
4. Chicago, IL
   Metered parking zones are extensive and expensive. The city leases its parking to a private company, limiting flexibility.
   How to beat it: Use the ParkChicago app to avoid overpaying. Consider monthly parking passes if you work downtown—see BestParking.
5. Los Angeles, CA
   Street cleaning rules and high demand in neighborhoods like DTLA, Hollywood, and Santa Monica make parking difficult.
   How to beat it: Look for LADOT-operated garages for affordable rates. Use Fluz to earn cashback with a CVS or Starbucks gift card if you’re grabbing something nearby while parked.
6. Seattle, WA
   Narrow streets, variable enforcement hours, and limited downtown parking availability create daily headaches.
   How to beat it: Use PayByPhone to stay on top of time limits. Consider parking in Capitol Hill or South Lake Union and walking or biking the last few blocks.
7. Washington, DC
   A mix of federal zones, residential restrictions, and pricey garages make parking tricky.
   How to beat it: Use ParkDC to find metered availability. Public transit (Metro) is a strong alternative—most stations offer parking at suburban stops.
8. Philadelphia, PA
   A dense downtown and narrow colonial streets contribute to ticket-prone parking.
   How to beat it: Book garages through BestParking and always double-check signage—many zones flip rules based on day or hour.
9. Denver, CO
   Parking is becoming more competitive as downtown grows, with time limits heavily enforced.
   How to beat it: Use SpotHero to secure affordable lots. Consider pairing errands with cashback at retailers like Target using gift cards from Fluz.
10. Miami, FL
    Tourist congestion, valet-only zones, and inconsistent signage make parking unpredictable.
    How to beat it: Use PayByPhone for metered zones and check out private lots in Brickell and Wynwood for better availability.

The Bottom Line

Bad parking cities don’t have to ruin your day. By using mobile apps, booking in advance, and taking advantage of cashback platforms like Fluz, you can reduce the stress and cost of navigating even the toughest metros.