What kind of comparisons are you looking for? I’m a Singaporean, but have not tried Chicago public transit. In the US, I’ve tried public transport in San Francisco, but only in the city centre and not the suburbs (was on holiday). I’m also familiar with public transport in London (Zone 1-2 only, where I lived for 3 years), Tokyo (on business), Paris (on holiday), and a few other minor cities.
As transport, it’s comparable to London and Tokyo. Trains are relatively reliable (more reliable than London, about the same as Tokyo), but there have been a few upkeep issues lately. Bus service is generally acceptable with wait times of about 5-10 minutes, and gets you to almost wherever you want to go (as good as London, I didn’t take the Tokyo buses much).
It’s clean. London was a bit more grubby than Singapore, Japan on the whole was a bit more clean in some places.
It’s safe. Nobody I know of has ever been mugged on public transport here, although I expect some minor cases of pickpocketing probably exist, as in every public transport system in the world.
It’s relatively quick. Keep in mind that you can get across Singapore less than 1 hour by car, so it’s not a big place by any means. It would probably fit into Zone 1 and 2 of London alone. Taking a train across the country would take you perhaps 1 hour from East to West.
My parent’s place is in a “suburb” (if you could call it that), and door to door from home to workplace, I took about 1 hour to get to work (in the central CBD area). I would walk to the nearest subway line (10 minutes) wait for the train (5-10 minutes), ride the train (20 min), change lines, including waiting for the new train (5-10min), ride the remaining 3 stops (10 min) and walk to my office from the subway stop (5 min). All in, about an hour.
Currently, I live 15 min bus ride from my office, but that’s unusual.
Certainly, people do get by without cars. My mom doesn’t have a drivers licence, and she takes the train to work every day.
I have a weekend car, meaning that I can only drive after 7pm and before 7am on weekdays and all day on weekends. For this, I got a S$17,000 rebate off my Certificate of Entitlement (“licence to buy a car”). For the record, I drive a Nissan Latio (Versa in the US), and at the time it cost me S$43,000 (US$ 34,388) after the rebate. The COE is good for 10 years only, after which I need a new COE. The COEs are priced according to an auction market (you “bid” for a limited number of COEs, which drives the price up as demand increases), and the government has been reducing the number of COEs available. Thus, the price has gone up recently - a New Toyota Camry is now at about S$168,988 (US135,147).
I don’t really need a car to get to and from work, but it is nice to have one when running errands. Of course, I could just take the bus, but eh.
Since the cost of the COE forms the bulk of the price of a car, people tend to just buy new cars. My dad never kept a car past 3 years, and always bought new.
If there’s anything specific you’d like to know, just ask.