I would guess a chipmunk would prefer to be moved during the day, rather than after they have gone to bed. I have noticed with some if there is a strange noise during the night it can cause them to get up, and they seem unsettled.
Alans trips with his chipmunks are the exception I think, and possibly most chipmunks could get used to travelling. Mostly though they will stay in whatever nest or hideaway you give them.
Unless you have bred the chips and they never get ill and need a trip to the vets, they don’t normally get to travel. They are very much territorial animals so their world is the world is the one they have scented out and have various stashes of food around, much like in the wild.
If your chippies aren’t used to travel and are normally shy I would suggest covering their travelling cage up. Some chippies are very outgoing, and like Alan says seem to like looking around during the trip.
If I’m taking a chippie in the car I try not to add to their stress, so I keep the radio off, not sure but I think it may help the nervous ones. I also will put my hand in their cage during the trip if they are very used to me handling them, just to try to reassure them. I wouldn’t do that with a really nervous chippie, as they tend to make for cover and keep really still. But even if they are the nervous type, always let them hear the sound of your voice, say their names, if you’re the person who feeds them. That must give them some reassurance.
At the destination if settling in to a new home I would just open the travelling cage once it’s inside their new aviary and let them make their own way out when they thought it was safe, rather than tipping them out.
The most worrying thing on a trip for me is if they don’t make a move, all sorts of things go through your mind, like have they had a heart attack or something. So it can be more stressful for the owner than the chippies.
