1

As a native Castilian Spanish speaker, I don't have problems understanding Chileans when you speak Spanish. Context is many times enough to figure words used in Chilean Spanish that aren't used in Castilian Spanish and when it isn't it's as easy as to ask the Chilean about the meaning of that word.

2

I think it's less the "Chilean Spanish" than the person speaking. I recently watched a video excerpt of the movie No! with a speech by Patricio Aylwin and understood everything, whereas there are other people speaking where I don't understand much.

3

This English speaker thinks its reputation as the "most difficult" Spanish accent is well-deserved. When I was doing my big South American backpacking trip, I definitely had more trouble understanding what was being said there than anywhere else, a combination of the accent and the idiosyncratic local slang. The difference from Peruvian Spanish or Argentinian Spanish is quite remarkable.

This is not a value judgment, of course. It simply means Chilean Spanish deviates the furthest from Spanish as it is generally taught in North American schools and universities, so it takes more getting used to.

4

Although I now understand Chilenos, I understand how it is difficult to understand for non natives. It isn't limited to the choice of words, but also to the rhyme. Chilenos, as well as some other dialects speak very quickly and therefore are more difficult to understand for those who aren't fluent. In English New Yorkers have a similar well earned reputation. Cachai?

5

Personally I found Cuban spanish the most difficult to understand whilst Peruvian was the easiest. Listening to Cubans was like listening to Scotsmen speaking English, you know its there, but you really have to concentrate

6

I'm pretty much in agreement with bjd at #2.

I was in Chile for only a few days, but I had no problem understanding people. I had gone there with an Argentine cousin from Tucumán, and when he complained to me that he had trouble understanding Chileans I replied that the ones I had met so far spoke more clearly than many of the people in his home city. My contact with "real" Chileans was limited, though; hotel staff, waiters and waitresses, taxi drivers in Santiago and Viña del Mar, and the steward on the bus between those cities. All in the tourist trade, so maybe they spoke more clearly than the average person.

7

I've spent nearly 6 months in Chile spread across various trips, including one very long trip where I also spent a lot of time in Arg and Bol tracking back and forwards into Chile and out again from Arica to Tierra del Fuego. Chilean accents vary considerably by region and by social class, just as in Britain. In general I found it easiest to understand in the far north, where people generally speak more slowly, though not as easy as Bol and Peru. In Santiago, just as in London or Dublin or Manchester, it varies markedly by social class, so bankers and newsreaders would be no trouble to understand, but shop assistants and streetsweepers could be rather tricky. Though some people can switch on a more careful speech that is easier to understand. I'd get to the point where I thought I could understand most people, then I'd go so some other place and meet people I couldn't understand again. For example, Valdivia has a really weird up and down sing-song accent I found difficult. Chiloe has an impenetrable accent, at least when you meet someone in a village digging his lot, but the pharmacist in town spoke a more standard form I had no trouble with. Down in the very far south, the accent is closer to Argentinean (whisper it quietly). In Aysen, it was curious travelling from Trevelin (in Argentina) to Futaleufu - only a short distance into Chile and until fairly recently only connected to the rest of Chile by several days journey on a mule-track - and finding the people, architecture and culture in Futaleufu so distinctly Chilean and quite distinct from the Argentinean settlements a short distance along a long-standing road across the border.

8

You all have great points! The level of understanding varies from social class, age or part of the country you're in. In each of this categories, there are different words (slang) and accents, but that's what makes each region so special. For instance, here in Chile we say people from the south speak "cantadito", which would translate to "singing", or if they use certain words you just know they're southern, which I'm sure is the case in your countries as well. But is nice to know that we are not completly misunderstood!

9

I found Chilean Spanish certainly more difficult to understand than the Spanish in some of the other countries, but I found Argentinian Spanish definitely a lot trickier.
The most incomprehensable Spanish accent I've ever come across was that of Puerto Rico!

10

I definitely found Chilean Spanish much harder than anywhere else. When I was backpacking in Latin America, I started with spanish classes in Guatemala and then progressed through Honduras, Colombia, Peru & Bolivia and finally Chile over a period of seven months. In each country I always felt like I was gradually improving, and by the time I got to Peru my confidence had increased enormously. And then I arrived in Chile and it felt like I'd gone massively backwards - I had real troubles understanding. So certainly as a native English speaker with basic conversational spanish I'd say it's definitely the hardest

11

I think I have to take back what I said earlier. I just went to see the Chilean film No! and had a hard time with nearly everyone except Gael Garcia Bernal, who is Mexican. Fortunately, there were subtitles. Since I read faster than they talk, I could understand more because I was expecting certain words or expressions.