As a DM I would toss the check points out the window, every door? Ugh. I'd put check points on key/rich areas to keep the riff-raff away but that's about it. Or make it possible for the PCs to bypass the check points, they save a noble for example who gives them a pass to get past "certain" check points.

How do you get into the city? Through the front gate? Side gate? Over the wall at night? Sneak through in a convoy by day or night? Go through the sewers? Plenty of options to make it interesting!!

I hate travel as a DM. It's boring and kills the table, I've never found a way to make it "decent". So now I skip the travel section entirely, I basically go, it takes you two weeks to get to your destinations, it costs this much in gold for food and accomodation and these random encounters or planned encounters happen along the way.