The picture is of The Badlands National Park in South Dakota.....
This is ironic, you being from Chicago! We started our trip by taking I-90 east to Madison, Wisconsin, and then Hwy 12 to Spring Grove, Illinois where my brother lives, him being a Chicago beast!
We watched his son get married, and then all four of us mounted up, rode Hwy 11 to 34 (?) The Great River Road which we rode north to Lacrosse and headed West on I-90 again, which is one of the most scenic freeways in America. You could do a lot worse on a cross-country route. West on Highway 2 is good, too.
If you decide to go West of the Mississippi, the following route might do you well: I-90 to Wall, South Dakota (be sure to visit Wall Drug -- damndest drug store in the world!), then tour the Badlands National Park. Continue on to The Black Hills and Custer State Park. Ride every road there, including especially Iron Mountain Road, The Needles Highway, The Wildlife Route through Custer State Park (watch out for buffalo!), the Spearfish Canyon road, and be sure to visit Mt. Rushmore, Leadville, and Sturgis. Get back on I-90 and go to Devil's Tower, Wyoming. Camp in the KOA and put up your tent so the Rock fills the back window. In the morning, watch for the first light striking the tower. Will make a believer out of ya!
Get back on I-90 and head west on what was once the Bozeman trail... If you are an old West Buff, visit the sites of old Fort Phil Kearny and the sight of the Fetterman Massacre. Then go on to the Little Bighorn Battlefield Monument. Ride the road along Last Stand Ridge after listening to the Park Rangers describe the battle. Visit Reno's hill and gaze at the meagre trenches the soldiers scraped out with pocket knife, canteen half, and tin cups, and try and imagine how that was....
Go on to Red Lodge, Montana, and wait for a clear morning and then ride Beartooth Pass and Chief Joseph Scenic Byway into Cody. You'll never be the same. Leave Cody, and enter Yellowstone N.P. (heavy construction at the beginning of the park tour), ride around it and exit South to The Grand Tetons. Again, you will be changed forever...........trust me!
At Jackson's Hole, say good bye to whoever you are with, and get home to Chicago however you can. Then box everything up, sell it, and move to Red Lodge as we are thinking of doing! Whew! Sorry, didn't mean to get carried away! But to tour the American West on a Goldwing is a possible dream -- a dream unavailable to most of the people in the world. Do it! Do it now!