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Avoid driving in downtown Chicago if at all possible. Traffic is awful, pedestrians are constantly wandering into the street out of turn, and garages in the Loop can cost as much as $40 per day. And although downtown streets are laid out on the grid, many have multiple levels which confuse even the most hardened city driver. Even outside of the city center, street parking may not be readily available. If you do find a spot, check street signs to make sure that a) no residential permit is required to park here and b) parking is not disallowed during certain hours for "street cleaning", rush hour or something along those lines. Parking restrictions are swiftly and mercilessly enforced in the form of tickets and towing — be especially wary during snowy weather.
Parking meters are mixed between old coin-op meters and newer one-per-block kiosks, which will issue a slip for you to put in your front window.
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Be advised: talking on a handheld cell phone while driving is illegal in Chicago, and the police are eager to write tickets for it. If you need to take a call, use a hands-free headset — or better yet, pull over.
The perpetual construction is bad enough, but drivers on the city expressways can be very aggressive. For those used to driving on expressways in the Northeast, this may be a welcome reminder of home. For everyone else, though, it can be intimidating.
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