San Jose, Costa Rica to Chinandega, Nicaragua

Not sure abou the convenience of buses asapect of your question but if you want a more pleasant city to stay in then go to Granada.

Managua would be OK if you choose a good hostel for the night where you can just relax and eat some dinner and are not bothered about having a look around.

I think Lana has already been in Nicaragua and knows the ropes, if I recall correctly.

If you are not in a big rush Lana, you can see some sights and always catch a bus hourly from Liberia to Nica border, then a bus to Rivas, and points north. Just a thought, if you want to travel in daylight. I agree, getting into Managua at night on a bus in that city would be a tad stressful.

Good Luck and keep us posted.

Tim

Just curious, why Chinandega? I spent a few nights there, and in comparison to other off-the-gringo-trail cities, I didn't much care for it. Not to mention some pretty bad stories from other travelers ... but, if you want to go there (avoid the neighborhood/city El Viejo), I'd suggest not arriving in Managua at night. Stay in Rivas, and catch a direct bus to Managua early, then an express to Chinandega from there. That would be the quickest and safest option.
Masaya and Esteli are two much more appealing cities off the gringo trail, IMHO. And if you're just looking for something in that area, Leon is a much better destination than Chinandega. Again, IMHO.
Not that Chinandega is horrible or anything ...

Granada is definitely the better option than Managua just to stay the night, but has the disadvantages of being a wee bit out of the way, and not having direct buses to Chinandega. The fastest way to get to CH, while avoiding Managua, may be to stay in Rivas, as mentioned above, and get on an early bus to Managua and from there on the expreso minibus to Chinandega. Or stay in Masaya (more interesting than Rivas) and take a direct early morning expreso chicken bus to Chinandega, with no need to change buses in Managua.

If you want to stay in Granada, you can take an expreso minibus to Managua (UCA) in the morning, and change there for the minibus to CH. There may not be many minibuses to CH later in the day though, so you can also take any minibus to León and change again there for CH.
To get to Granada, you'll have change buses at the turn-off to Granada/Masaya just past Nandaime on the road from the border to Managua, or at Nandaime itself, and wait for a bus to Granada.

I say stay in Granada (way less terminal-to-hotel-to-terminal hassle than staying in Managua), then the 1 hr minibus ride to managua in the morning. Leave Granada at 8am and you'll be on the bus to Chinandega by 10. Easy!

Dunno which version of the LP you have, but I was kinda surprised by the amount of coverage that the Nic & El Sal book gave to Chinandega... it really is just a stopover to more interesting places in the region, but in that book it has a map and all these different hotels when (as others have pointed out) there's really very little reason your average traveler would be there for longer than a night...

I don't see any downside to staying in Granada, in fact I think transportation will be easier that way. Considering the long journey it isn't that far out of the way, especially if your bus to Managua stops there anyway. It's like a 20 min detour off the regular route. You get off the bus in Granada and depending on where it drops you you walk or short cab to your hotel. Then in the morning you most likely walk to where the microbuses leave for Managua (they say UCA, becaues they go to the bus stop across from la universidad centroamericana in Managua, and they leave about a block away from the parque central in Granada) and once at the UCA stop you just get on the microbus 20 feet away that goes to Chinandega. It is (usually) faster and more comfortable than the regular buses.

However, If you go straight to Managua you have to taxi to your hotel and then in the morning taxi to UCA, or if you spend the night elsewhere and take a bus from Rivas to Managua you will end up at Mercado Huembes and have to take a cab either to Mercado Isreal Levites where the regular buses leave for Chinandega or to la UCA for the microbus (uca is closer to huembe than levites). Considering the level of concern people have about moving around in Managua I wouldn't suggest this unless you feel comfortable with it.

I'm getting picked up in Chinandega to go to Monty's Surf Camp in Jiquillio where I'm working for the summer. I think that I am going to spend the night in Managua. I have a friend who informed me that there is a decent TICA BUS HOTEL for cheap right at the terminal. From there in the morning, I believe I'll need to take a taxi to the Israel station and then to Chinandega. Thanks for everyone's help!