I've taken many cross country trips on maxi-scooters and motorcycles. I just bough my 2013 C 650 GT in Long Beach, California and rode it to San Diego then cross country through Nevada, Utah, Colorado, Kansas, Missouri and Illinois to Chicago.
IMHO, things you need for a cross country ride (not necessarily in order) are:
1. Good rain gear, nothing is as miserable as riding cold and wet.
2. Good gear in general (quality riding pants/at least kevlar jeans, quality riding jacket, at least some way to go down to mesh in warm months, quality helmet, varying riding gloves, good protection and ones that will keep you drier and warmer as well as not to hot for warm weather, shoes or boots that offer some foot and ankle protection. ACCIDENTS CAN ALWAYS HAPPEN.
3. Extra pair of glasses if you need glasses,
4. Either a helmet that has sun shield or dark shield or sun glasses.
5. Sun screen if you burn easily and mosquito repellent.
6. A cooling vest is nice for Kentucky in the summer.
7. A few tools, (something that works the torx if it's your BMW, screw drivers, robo grip (plier), air gauge, lots of people like to bring a tire repair and small air compressor but I've generally not brought them, motorcycle size jumper cables, but I've not always brought them.
8. Small first aid kit, at least including a couple different bandage sizes and antiseptic or antibiotic cream
9. Normal items like cell phone, music player, GPS or your cell phone has GPS.
10. Either maps for all the states you'll be in or an atlas book. GPS doesn't replace the value of maps.
11. If you're packing some of the items into a bag to go on the luggage rack either that bag should be a true waterproof bag or bring several contractor's bags to put over the bag attached to the bike.
12. Clothes that can layer in case of cold or a heated jacket liner.
Not on the subject of what to bring, but on safe riding. Taking plenty of breaks so that you stay alert is a very good idea. Two hours is a very long time for the average motorcyclist to keep up their attention to the high level they should have. Especially if you haven't made many or any of these trips before 15 minutes off the bike for every hour on the bike is a good idea. On the same subject remember the effects of the wind and weather on your body. If it's sunny and hot your body is loosing hydration not only to the heat but to the wind. You need to keep drinking fluids even if you don't feel that thirsty. The same kind of effect comes from windchill. 32 degrees on a day with no wind will produce a windchill effect of 10 below zero if you're on a bike going 60 MPH. If you're riding in gear/clothes that don't keep your core temperature up you'll quickly sink into a more debilitated physical and mental condition. The same kind of effect will happen to your body in high heat. If it's 95 degrees and sunny your body is using up it's hydration faster then you're going to replace it and your core temperature will rise to a dangerous level quickly with the hot wind of riding. If you don't have a cooling vest take your riding jacket and gloves into a bathroom and pour water all over them. This will protect your skin from having it's hydration leeched away as fast and it will keep your core temperature from rising as fast.
If you have any doubt about your physical condition or feel listless or drowsy it's time to get off the bike for a break. If it's raining hard and you have lost faith in your visibility through the helmet shield it's time to take a break.
Always check the oil, inspect the tires and check their inflation and do a visual once over of the bike. Also if anything seems wrong with the bike question whether taking it on the road is a good idea, especially if you're going by yourself.
Something like AAA is a good idea. I have AAA Platinum which covers motorcycles and RVs as well as cars. They also give you free maps.
I live in Chicago, like you, and you know we just don't have any good riding roads around here. So my riding buddies and I will head up to either the Baraboo area or the Kettle Moraine area in Wisconsin for a Saturday or Sunday day trip. Depending on our routing we'll ride between 300 and 450 miles on one of those day trips. One or two of those kind of day trips are a good idea before taking off for a true highway trip. If you feel that you ever want to go along on a ride like that with our group, drop me a note.
Different people have different ideas about routing a trip like the one you're talking about. Some people will avoid the interstate highways at almost all times. I'm of the view that I use the interstate highways through the boring places and go to the country roads in the interesting places. As an example of what I'm saying my riding buddies and I make a number of weekend trips each year to to the Tri-State (Indiana-Kentucky-Ohio) area to ride the hills and turns around the Ohio River. We will generally leave Chicago on the interstate following the interstates I 90 or 94 to I 65 til we get past Indianapolis. Then we'll either get off I 65 at Columbus, IN and take the country roads or take I 74 out of Indianapolis to Greensburg, IN and country roads after that. This gets you through the boring parts fastest and leaves the most time for the good roads. Also we'll generally stay on the interstate or major roads after dark. After dark the interstates are a lot safer because you're much less likely to hit wildlife. When making this kind of trip one of the greatest risks is hitting wildlife especially deer.
Two years ago I hit a deer up in Kettle Moraine, WI with my Burgman Executive coming hot through a turn (maybe still going 45 when I hit the adult deer) and am very lucky that the damages were only a soar knee and some fiberglass on the bike. In the last five years or so that I've been doing cross country riding I've come very close to hitting deer more then 10 times, I stopped in Wyoming when I saw an Elk in the road and he put his horns down to charge when I saw that I took off again fast, I've had near misses from cows in western open range states hit a Coyote and several small possum or raccoon types. On this last trip from California I was in Colorado having just come down over Independence Pass and they actually warned me (Sign that said wildlife present motorcyclist use extreme caution lit with yellow lights), but it was dusk and I was tired. So like a fool I passed the two cars in front of me that were going 50 in a 60 on US 24 through the mountain forest. The next thing I knew a full grown male Elk ran 10 feet in front of my bike with me going around 60. I was just lucky to get away with being that stupid.
I've also had a two foot by two foot sage brush blow into my Silverwing about five years ago, on US 54 in New Mexico, scratch up the bike and gashed my calf. I should also give honorable mention to having low sided on an FJR at 65 a couple years ago very late at night on I 90 a few miles west of O'Hare due to my front wheel getting tangled up in a piece of truck tire tread.
Saying all of this I'm not trying to scare you from cross country riding, I'll do it at any opportunity. The combination of the adventure of the road, the road with my music going into my helmet, people you get to meet, and beauty of the countryside call to me like a siren. At the same time in seven years and over a hundred thousand miles of adventure/road trips I've been down twice. Once a couple years ago on I 90 and this spring on the Blue Ridge Parkway in Virginia. This spring on the BRP I was racing the mountain top turns on an FJR against my friend with a BMW R 1200 R and I took what was probably my 200th curve late in the day going around 75. As I got into the turn a little hot there was grass clippings that I slid my rear wheel on and I did a high side. The bike was wrecked, I slid on the pavement hitting down at 50-60 and came to a stop. I was wearing good gear from toe to head. The crash wrecked my gear, Firstgear TPG pants, Olympia Transition Jacket, Scorpion EXO 1100 Full face helmet and Olympia riding mesh gloves. As the dust settled I realized that my parts were all still there and my riding buddy was looking down at me. I took a minute to collect myself and got on to my feet. I was pretty lucky, I never had to go to a hospital. I twisted an ankle that just finishing healing, cut the side of my hand where the glove had pulled off, and cut my knees against the hard knee pads in my riding pants, and cut my nose on the face shield of the helmet. Six weeks later the cuts are all healed, my ankle is about 90% and my insurance paid for the bike and gear. Without the gear I'd have been facing skin grafts, and possibly broken bones as well as probable head injuries. Instead my insurance money bought me the BMW C 650 GT and new gear with money to spare and I got to do a fly and ride to Long Beach, CA.
Good luck with your trip plans and definitely have fun.
BTW, one other pointer that the IBA has for endurance riders. Never add things to your bike right before a trip! Aftermarket horns, lights, electrical devices or anything that could affect the way the bike runs without the chance to test them around town for a bit should stay off till your back home.
