Road Trip from Chicago Suburbs to Maine with a 2.5 Year Old and a 3 Month Old

That sounds like a long trip! I wouldn't worry too much about the little guy. At that age it's pretty easy to travel b/c they really will sleep most of the way. I'm not a huge fan of getting in the back seat with my kids during road trips, but on such a long trip you maybe want to consider doing it for a couple of the stints in between feedings. I wouldn't sit back there the whole time, but since he's so little and rear facing you may want to consider sitting there for a just a bit to play with him during his normal awake time so he doesn't sleep the entire time and then stay up all night.

Other than that, I'd say plan on taking your swimming suits and swim as much as possible in the hotel pool to wear out your 2.5 y/o. If possible, I'd even swim for an hour or so BEFORE you leave the hotel in the morning so it increases the likelyhood of him sleeping while on the road!

Good luck!

It sounds like you have some good plans. When our kids were little and we traveled a distance, we would leave early in the morning (like at 3 or 4 in the morning). The kids would sleep in the car, and then around breakfast time they would wake up, and we would stop. In the afternoon we would find a camping area or motel and stop for the day. We would also try to find an activity or two to stop and do along the road. I also made a goodie bag which the kids could draw a special gift from each day. Include favorite toys, snacks, and drinks. Have a great trip.

You seem to have a good plan.
And yes, make frequents stops to stretch, nurse, get out of the car, as needed.
Plan on being flexible. Because the kids are young.
If you can, sit in the backseat with your kids.

My daughter was a little older when we made a huge trip like this. the lights from the night driving bothered her. like when a car passed us and made shadows on the window and roof. you might want to think about covering his seat with a dark blanket to blocks some of that if it ends up being and issue sounds dumb but we didn'trealize why she was screaming right away.

No experience on that particular issue but it sounds like you've got all the bases covered. As long as you're flexible, it should go fine. My only thought would be about traveling at night. We did this when my kids were little (my younger one was VERY difficult) and it worked great. Adults just traded out driving duties so neither of us was wiped out. With your little one being SO little, I'd take advantage of those longer stretches of sleep. Good luck-have a great time!

I could have written this question! We are driving from Orlando to Blue Ridge, GA at the end of this month it's a 9 hour car drive and we have to check in between 3-5pm. When we leave we will have a 2 year 4 month and a 3month 2days little girls. When my oldest was 4 months old we drove to Ill and it wasn't to bad, we did stop overnight and I would pump in the car and feed her bottles so that we didn't have to stop as often. This time I will bring my hand pump, but I'm sure we will be stopping for the two year old.
We plan on leaving at 3am so that they hopefully will sleep in the car for at least a little while. That will also give us 3 hours of wiggle room before having to be there. This way we can hopefully go until at least 7 before stopping for breakfast. I am going to go to the dollar store and pack a little backpack full of new toys and treats for my two year old. She has a little Dora tray that attatches to the car seat so she can eat and color on it. It's soft foam so it's fine incase of an accident, but it is study enough to lean on. I am a huge fan of color wonder markers in the car, they work only on the special paper. They also have like little coloring pads that are great for the car, papers won't get everywhere because they are attached and they are smaller than regular paper or coloring books.
I also plan on moving the car seats around so that I can go back and sit between them if needed. I don't plan on spending the entire time back there, but I'm sure it will help keep them entertained.
Good luck and have fun on your trip!

Is flying totally out of the question? We have driven from Chicago to PA several times and this year by the time we factored in gas/food/hotels it was actually cheaper to fly. Not sure where in Maine they are but you can sometimes get good deals on Southwest to Manchester, NH.