Option 1: Order on the Django/Python layer

The items are first sorted by user_id, and only in case of a tie, it takes the one with the latest date. But that means that you eventually get for each user a Chats object, ordered by the user_id.

I think here your only option is to sort it at the Django/Python level, so wrap it into a list, and sort by the date:

from operator import attrgetter

items = list(Chats.objects.order_by('user_id', '-date').distinct('user_id'))
items.sort(key=attrgetter('date'), reverse=True)
# work with items

and then render the items in the template.

Option 2: Annotate the User model instead

Another option is to annotate the User model and thus work with a QuerySet of User objects:

from django.db.models import Max, OuterRef, Subquery

User.objects.filter(
    chats__isnull=False
).annotate(
    last_date=Max('chats__date'),
    last_message=Subquery(
        Chat.objects.filter(user_id=OuterRef('pk')).order_by('-date').value('chat')[:1]
    )
).order_by('-last_date')

Here the User objects will have an extra attribute .last_date with the latest date time of the object, and .last_message with that message.

Note: It is normally better to make use of the settings.AUTH_USER_MODEL [Django-doc] to refer to the user model, than to use the User model [Django-doc] directly. For more information you can see the referencing the User model section of the documentation.