Park it

When we started asking around for Loop parking tips, we learned one thing: People are loath to share their secrets. “No dice,” one friend said. “If you print the location of the meterless street where I park, the city will make sure it isn’t meterless anymore.” To be sure, with some Loop parking rates as high as $27 a day, it’s every man for himself when it comes to scoring a spot. But if you just can’t leave your car at home, take these strategies for a spin:

Stick to the outskirts of the Loop and the streets just beyond it.
For the most part, the more centrally located you are, the more you’ll pay. We found free street parking all along Wabash Avenue and State Street just south of Roosevelt Road, with restrictions only on Bears game days. Those same streets between Roosevelt Road and Congress Parkway are lined with meters, but that means you have to feed them every two hours, and you can’t park at the meters during weekday rush periods (7–9am, 4–6pm). Just behind the Art Institute, Columbus Drive has loads of metered parking using those fancy new pay boxes—a deal only if you don’t plan on staying more than a few hours. The unending construction and gentrification in the West Loop means few parking finds these days, but if you’re willing to venture as far west as, say, Racine Avenue, you can score spots on some of the side streets, then catch the 20 Madison bus into the Loop. Parking lots are cheaper on the fringes, too: We found a CPS lot at Polk and Clark streets advertising for $9 a day, and another just to the west across the street from the River City condos, for just $6 a day if you’re in by 8am.

Get there early.
Haul your ass out of bed instead of hitting that snooze alarm and you’ll beat traffic—and score discounted parking like the River City deal above. Almost every garage and lot in the Loop offers some sort of early-bird discount—usually a buck or two off the regular rate if you’re in by 8am or 9am (not 9:01, trust us). There are many lots along State Street just south of Congress, where the rates average between $9 and $11 for weekday parking—but they’re packed to the gills by 9am. After 10am, you’ll be hard-pressed to find a space in the Loop that advertises a rate under $17. Coveted streets where there are no meters and no restrictions—like along Wells Street just south of Congress—usually fill up soon after the sun rises. The deals start up again—and meter spots are back in abundance—throughout the Loop starting between 6 and 7pm.

Try a little tenderness.
A student ID shaves a few dollars off the rate at many parking spots, but we’ve found that a nice smile can take the place of any proof that we’re hitting the books. Valets at some of the big hotels in and near the Loop will hold onto your car for a couple of hours if you tip well and ask really nicely. And friends who’ve negotiated group rates for some of their coworkers at Loop garages have scored free parking for themselves in the process.