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Bitly is one of the oldest and largest link shorteners, meaning you can trust that it won't go away anytime soon.
Pro Widely trusted
When people see a bit.ly link, they don't usually think, "ooh sketchy link".
Pro Customizable domains
You can set up bitly to use a custom domain, so you don't have to develop or maintain your own.
Pro Flexible and easy to use API
The bitly API provides jsonp callbacks, XML, CORS, and data metrics. The API is simple, and easy to use with good documentation. It is clearly thought out and is up to date with support for new API technologies.
Pro Shortest and multiple short domains
Bitly provides bit.ly bitly.com and j.mp
If character count matters, you cannot get a domain shorter than j.mp
Pro Protection from malicious sites
Anti spam measure and tools mean people that follow your bitly links can be confident that they won't lead to a dangerous site. Bitly links cannot be changed, meaning a trusted link will stay safe.
Con 500$ on enterprise
Con Cannot edit the destination URL as a free user
This is one of the main purposes of using a URL shortener.
Con Limited clicks for free users
10k Clicks a month, if you want to add an branded domain then you only have 500 clicks a month for that. You want more? $950 per month for their business plan.
Con Errors often
It will often claim that it couldn't shorten a url.