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Are you under any proxy server?
Does your internet connection show continuous flow of data?
Have you tried without using www?
Can you open https sites like gmail & facebook?
What is the output of following commands?
My guess would be DNS. Can you ping the sites by name?
$ ping -c 2 hotmail.com
You can lookup the dns on sites like network-tools.com and add entries in /etc/hosts to do the dns lookup locally. Not a long term solution, but it can help rule out the culprits.
On dialup long ago, I had to fiddle with the MTU size for some sites. Some required a full 1500 (default) others only worked with 576 (dialup size). Crazy times and only seemed to affect poorly configured servers.
I have not had any direct experience with it, but I have read here of issues such as yours being resolved by turning of IPv6 in the network configuration; again, though, I have no personal experience, so take that with a grain or two of salt. Here's an article from the Ubuntu wiki (your user agent icon says you are using Ubuntu) that might help:
Chrome has had a problem for awhile. Sites you try to load from a link from another site don't load normally. You can get them to load by clicking on the maximize/restore button. Maximize it if it's not already mazimmized, or unmax it if it is. You can then put it back to where it was. It's a pain, and seems to have been fixed in the latest dev channel builds. Not sure about beta or stable.
www.site.TLD and site.TLD should be swappable. Granted that some sites misconfigure things so only one or the other works. But many browsers will prefix www. on the name and try again if it doesn't work the other way. And postfix .com in a few cases as well.
Your ping resolved the IP address so DNS is working, but you had 100% packet loss. A site doesn't have to respond to icmp packets. Although most of the big company ones do. And I can ping that one with the same IP you resolved. You got an IP for the site, so the DNS part is working. There could be some routing issue, or some firewall rules that are preventing things from working as expected. Perhaps traceroute or other things might help identify the issue.
The problem is now intermittent and easily solved by rebooting my 3G gizmo until Hotmail finally shows its face. Knowing very little about IP, DNS etc but enough to know about having to have a unique addresses, I suspect that all your suggestions about IP address allocations and things way over my head, are correct.