When comparing Python Weekly vs CheckiO, the Slant community recommends CheckiO for most people. In the question“What are the best resources to learn Python?” CheckiO is ranked 18th while Python Weekly is ranked 32nd. The most important reason people chose CheckiO is:
Users can publish their solutions for different problems and other users can review the code and give their opinions on how they would have solved the problem. Sometimes, some of the most active users get their code reviewed by Guido Van Rossum (the creator of the Python language) himself.
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Pros
Pro Has a jobs section
Both the newsletter and a section of the site covers jobs that are available for Python developers.
Pro Keeps you updated on all things Python
The newsletter is a includes curated news and articles as well as keeps readers up to date on various tools, libraries and events that might be relevant to Python users.

Pro Community backed solution reviews
Users can publish their solutions for different problems and other users can review the code and give their opinions on how they would have solved the problem.
Sometimes, some of the most active users get their code reviewed by Guido Van Rossum (the creator of the Python language) himself.
Pro Available in multiple languages
CheckiO crowdsources translations for problems. Currently problems have been translated in 10 languages. So it's highly possible that eventually more languages will be supported.

Pro Ability to create new challenges
New missions can be created and uploaded using GitHub. After that is done, it's suggested to CheckiO and if it fills all the requirements after being reviewed by a CheckiO team member, it's pulled into the game.

Pro Challenges from GitHub, O'Reilly, Dropbox and Hubspot.
Cons
Con Not for beginners
While this is a great resource for Python devs to keep up to date with the scene, it's no a great resource for learning Python as a beginner. The resource provides no structure or courses.
Con Not for absolute beginners
CheckiO does not teach syntax, instead it teaches how to solve problems using a particular programming language therefore some basic programming knowledge is required to start.
