When comparing iMessage vs Skype, the Slant community recommends iMessage for most people. In the question“What are the best messaging apps for iOS?” iMessage is ranked 3rd while Skype is ranked 18th.
Ranked in these QuestionsQuestion Ranking
Pro Secure end-to-end encryption
Pro Cross-platform within Apple ecosystem
iMessage is available on iPhone, iPod, iPad, and Mac.
Pro Supports voice messages
Short voice recordings/messages can be quickly sent, and messages can be easily dictated into written messages as well.
Pro Free and unlimited messages over Wi-Fi and data
Messages clearly indicates whether messages are being sent over iMessage (blue) or SMS (green) where messaging rates apply. iMessages do not count as SMS messages with your carrier, instead they use a negligible amount of data to send over Wi-Fi and cellular data networks.
Pro Clear indicators for message delivery and receipt
The app indicates when messages have been sent, when they have been read, and when someone is typing.
Pro Comes pre-installed
No need to download or sign up for a new service
Pro Seamlesss switching between SMS messages
Pro Friends don't need to "sign up"
You can just message them using their existing phone number or Apple ID and they will get your message.
Pro Clean UI
UI is minimalistic, and clear. And there is a plethora of stuff on the left of text box if you wanna use them.
Pro Apps and games for iMessage are available
For example, you can play games like pool or you can show someone a destination to go to .
Pro Easily connect with others due to how popular the service is
There's a good chance that whoever you're trying to reach has Skype already set up and familiar with it, avoiding the hassle of installing and getting to know new software.
Pro Screen sharing
You can show your whole desktop, a select part of the screen or a specific window over Skype.
There's software for Windows, Mac & Linux and apps are available on iPhone, Android, and Windows Phone.
Pro Group video for free
You can hold video calls with up to 10 people.
Pro Available on Linux
A stripped down, minimalist version of Skype is available for Linux.
Pro File sharing
Skype allows you to send any files (MP3s, images, text, etc.) by simply dragging and dropping then in the chat window making it simple to share things with colleagues.
Pro Cheap fixed phone number
Starting at $5/mo you can get a Skype number.
Pro Send SMS and make regular calls
With Skype Credit bought or a subscription, you can send SMS and make direct calls.
Pro Group chat with archive / records
Pro Powerful 1:1 chat and also group chat
Con Not cross-platform
iMessage is not available on anything but Apple devices.
Con iCloud sync of message is not stable
Sometimes, the messages on different devices with the same ID will be different, the syncing function work poorly.
Con Slow and unreliable
Con Plagued by bugs on all platforms
Crashes and other bugs are prevalent on Android, Windows and other platforms.
Con Not a feasible alternative as a professional team chat
Missing key feature such as centralized mgmt, centralized billing, data retention policies, ...
Con Poor quality when screensharing
It is not possible to manually set resolution or bitrate, and Skype often defaults to a resolution so low that text is unreadable. It is also not possible to transfer control over mouse and keyboard.
Con Slow filesharing speed
Con Owned by Microsoft
Con Obnoxiously large ads
Ads take up over 25% of the usable space.
Con Poor Linux support
The version available for linux users is quite outdated, and does not support some of the newer functionality, such as the free group video calling and screen sharing.
Con Requires both ends to be online (if neither end is using a cloud-enabled device)
Messages are sent and received only when both ends are online, if neither end is using a cloud-enabled device. In this case, if you are online 9-17 and your recipient is online 18-3, messages will never be delivered.
Con MIcrosoft (Skype's owner) actively assists eavesdroppers
On the other hand, if you lose your copy of one of your conversations, you may be able to get a copy of it from your government with a little bit of luck and a public records request.
Con Subpar video quality with more than 5 users
Skype has significant problems with multiple users and video quality. Skype recommends that a max of 5 users group chat as video quality is severely affected. Even webcams tested with other chat services showed lower quality when used with Skype.