Yes, all of these schools have similarly strong recommendations. Some have different strengths and weaknesses but are similar enough in terms of reputations that I wouldn’t consider that a huge factor.
US colleges and universities are very diverse. Minnesota and Wisconsin are major research universities with tens of thousands of undergraduate students and many grad students. Minnesota is in a large metropolitan area (Minneapolis/St. Paul). Wisconsin is in a top-rated “college town” that one could call a large town or a small city. It’s the state capital and the capitol building is very close to campus. The Wisconsin campus is pretty well integrated with Madison (the city), which basically sits between two nice lakes, the campus being on one of them. Besides being the two large research universities on your list, these are will have very cold weather from about November-March. Some people are fine with that, some might find it hard to roll out of bed at 8 o’clock in the morning and walk a 1/4 or 1/2 mile to class with snow and ice everywhere. They are terrific schools.
McGill is also an urban campus and very cold. We visited the school and stayed a few days in Montreal. It’s a very nice, very bilingual (English/French) city. Miami of Ohio is also a large state university. It has a very beautiful campus and is in a smaller college town.
The others on your list are generally small liberal arts colleges (LACs). In the US, many students attend larger universities and many attend smaller LACs. Generally LACs will have smaller classes and closer interaction with professors, though you can have these as well at large universities. Wisconsin and Minnesota have large research facilities, especially for things like sciences, that you won’t find at an LAC. For professors, teaching is often the biggest focus at LACs and research at larger research universities. At Wisconsin, a typical introductory class might have a couple of hundred students and be all lecture. At Dickinson, they might have 40-50 students, rarely more than 80-100 and have more discussion. But now often larger schools require freshmen to take one small discussion class so that they get to know professors, have better writing opportunities, etc.
Neither option (large v. small) is “better.” One or the other might be better for a particular student, or in a particular field. But really they are just different options. A family might have one kid who is a better fit for a large university and one a better fit for a smaller school.
Puget Sound and Clark are more urban. Puget Sound is in Tacoma, which is more of a working, industrial sister city to Seattle, a major US city with lots to do. I know Seattle well, but not as much about Puget Sound/Tacoma. I love the Pacific Northwest (PNW). Weather is marine, so gray and rainy, but not very cold. Clark is in Worcester–nice campus, not the best area of the city, but Worcester itself has been improving a lot in the last couple of decades (had been very industrial). It’s an hour or so to Boston by commuter rail, which is a little costly but doable. Worcester is also cold and snowy. The travel advice above is good, and helpful.
As described above, the rest are small LACs in small towns. Social life tends to be focused on the campus, as their might be less to do in town/city. I know less about the midwestern LACs but can say Dickinson is an impressive school with a beautiful campus. It has about 2300 students. As noted, it has an international focus and is well-known for political science/government.
Connecticut College is also very good and is as described above.
What I can’t say is how a larger school like Wisconsin would appeal to you, in comparison with a smaller college community like Dickinson. One student might love one and not the other, and the next student might be exactly the opposite.
As noted above, almost all students have to apply to grad school after undergrad (well less than 1% of all students might be in program where, for example, they are admitted into med school when accepted undergrad, but this is definitely the exception and almost no one is doing this, and it’s very hard). If you want to go directly after undergrad, you apply your senior year, just like in high school.
Some grad schools/programs require or strongly suggest that students work for a couple of years before grad school. For example, students often work a few years before going back to get their MBA (grad business degree). It often varies by one’s field and by schools though. But that’s down the road.
Good luck!
Many colleges will just enroll you in a health care plan they provide and put it on your bill unless you can provide proof of other insurance that covers you at the college location. The cost of a year of their plan will vary by college - typically I’ve seen between $1500-$2000 for the whole year, but I have seen it higher at some schools.