On your way from Bozeman to Cleveland, stop by Minneapolis.
Not only is Downtown pretty legit, but from Downtown you can catch the lightrail to the Mall of America (the biggest mall in America.) You can do a bunch of shopping, see a movie, or just walk around and chill.
Then, go to Chicago and check out their Downtown scene. They don't have the biggest mall of America, but the shopping strips there are nice. Overpriced, but nice.
Hope this helps man. You might even want to skip Bozeman completely. Montana is boring, my dude.