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Tipping in Chile is not complicated, you will probably get the hang of it in a day or two. Just a heads up, tip in pesos, except in hotels, where you can tip in pretty much any currency. Do not tip in coins from your home country, even if you just gave them 20 Euros in coins, exchange houses won't exchange coins. You just gave him 20 Euros to make himself a paperweight.
TAXIS. NO TIP NEEDED. Street taxis (Yellow roof, black body) generally will give you exact change, or round it slightly up or down (CLP$2,670? You'll get change for CLP$2,700). They run on taximeters, just make sure they get it working when you get in. If the trip was fast, and efficient, you can round it up to the next thousand. E.g. Trip was CLP$3,700? Round up to CLP$4,000. Just say the magic words "Quedese con el vuelto" - (keep the change). This also applies to taxis out of the airport. Now, if the driver helped with your bags and was polite, maybe a full CLP$1,000.
HOTELS. TIPPING IS VOLUNTARY, YET EXPECTED. (Dollars widely accepted as tip) First off, tip when service is good/excellent. Do not feel like you have to tip because you read it online. That way you encourage better service. The staff members that receive tips are mostly Doorman, Bellmen, Concierge, Waiters, Bartenders and Room Cleaning Staff.
Generally, Doormen and Bellmen split tips in equal portions as a team. In small hotels a CLP$1,000 bill should be enough. In Five Star hotels, where you should expect better service, consider maybe CLP$1,000 - $1,500 per bag. A five dollar tip is already considered as a good tip. A USD$10 tip will ensure excellent service throughout your stay. If you didn't tip on your way in, remember to do so on the way out. And if you had 6 large bags and a case of wine and the doorman had a taxi waiting for you at the door, door open and a smile, the bellmen promptly had all your luggage tucked safely in the car, and all of them wished you a safe journey, man, you better tip if you don't want to be remembered as "the cheapskate with 6 bags and a case of wine" for the rest of the week. Winter tip on tipping: If the doorman or bellman had to be in the rain and cold for 10 minutes to get you a taxi, a tip is in order.
Concierges should be tipped when they have arranged tours or reservations for you, and given a variety of good tips for your enjoyment. No information? Don't sweat it. But if they really made your trip a memorable one, go ahead and tip CLP$10,000. Maybe more for great service. E.g: You mention in passing to someone that tomorrow you would like to eat somewhere nice with your wife. When you return, the concierge bids a word with you and has a few suggestions for you, and upon arriving to the restaurant, they are expecting you with their best table and an English speaking waiter. Yes. The concierge called ahead, got you the nice table and the waiter. Isn't that nice of him? I bet it is.
Cleaning staff are a bit trickier. If they do their job correctly, chances are you'll never see them throughout your stay. When to tip? Was the room made with care? You left a particularly messy room to find it spotless and... is that a different perfume in the room? Curtains open just so because you like to sleep late? They noticed you use gargantuan amounts of shampoo and they had an extra bottle for you? Out of mouthwash, and you find a small bottle by your toothbrush? If they seem to go out of their way to be excellent, do tip. Excellent service? CLP$1,000 per night. per person. Try to leave it in the desk of coffee table, with a note, if possible.
One tip about tipping in hotels. If you appreciated the service and kindness of one person in particular, like a Bellman who had some good tips, or a Doorman who greeted you by name every day and remembered where to send your taxi, or a Barman that joked with you when you were relaxing over a pisco sour, tip them in an envelope. In Chile most tips are pooled and split in equal shares. No, you didn't tip that guy 5 dollars, you tipped him 83 cents if he was in a shift of 6 people. If you want to recognize their service, remember that what they get in an envelope is theirs and theirs alone.
RESTAURANTS. TIP IS INCLUDED, BUT... In Chile, 98% of restaurants, bars, pubs and coffee shops will add 10% to your bill total (it should be properly stated in the bill). 10% is the expected bill if service was good. If your waiter or maitre d' were excellent, maybe consider something extra. In that case ask to add something extra to your bill, or leave it in cash. Leave 5% as a statement if you think service should improve. Leaving anything lower is bordering on insulting. Had a hundred dollar dinner and you are leaving ONE dollar? You have a 50/50 chance of the guy just handing it back to you and tell you you probably need it more than he does. If service is poor, then leave NO tip. That, at least, is not insulting, and the message WILL get across.
BEAUTY PARLORS. TIP NOT EXPECTED, BUT... If service was good and you got exactly what you wanted, tip the hairdresser or nail artist in cash. Your bill will not include a tip, so in this case, cash is king. CLP$2,000 should do just fine.
SUPERMARKETS. YES, DO TIP. The guys that work bagging your items work for tips, so CLP$200 - $300 should do just fine. The girl bagged everything nicely, keeping warm bread away from the icecream and double bagged the heavy stuff? go for CLP$500.