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At the time of this post, USD1 often written as U$S1 (USDollar) = $19.6 (Urugyuan peso). It's a little confusing to see $ but get used to it, that is the UYU peso, not dollars.
Restaurants: 10% of the bill
Baggage handlers at the airport/hotel: $20 / USD1 per bag
Housekeeping: $20 / USD1 per day of your hotel stay
Taxi drivers: $10-20. It's not mandatory but depending upon the distance of your cab ride, round up or simply add as appropriate for a cab ride within Montevideo
Delivery drivers: $20 / USD1. Establishments deliver to most places in Montevideo
Street parking attendants: $5-10 pesos is reasonable
Actually, the sign for uruguayan money is just $. In Colonia del Sacramento, and other places where everybody is used to tourists and foreign currencies, in most of the stores you´ll find signs like $U or UY$ for "peso uruguayo," $Ar for peso argentino and U$S for USDollar. In fact, it seems that just about anything that's expensive (U$S100 or more) has it's price written in USD.