Milwaukee, WI to somewhere in MT - help

My sister and I are planning a 7-10 day road trip. Starting in Milwaukee, WI and hopefully ending up somewhere in Montana. We are a little low on cash and hope to stay away from Tourist hot spots...but still want to see lots of cool stuff along the way. We had planned to take non-interstate roadways on the way there and the interstate on the way back. Any ideas of what to see, eat, stay, etc. We will be packing tents and camping gear. The main focus of this trip is to relax and see the sights. thanks for your help!! oh...this first "real" road trip (we went to SC a few years ago but drove straight through....at night).

Welcome aboard the RoadTrip America forum.

At its best what this forum does is let those new to the road have the advantage of the knowledge earned by those who have been there. For starters, read the reports from others who have driven this section of the country, here, here, and here. These should give you lots of ideas, but speak up is there's something else specifically in the way of cool sites you're looking for

AZBuck

The two obvious places I would target would be Yellowstone and/or Glacier N.P. Either could be reached in a pretty easy 7-10 day trip from Milwaukee. Both are certainly tourist hot spots, but they are that way for a reason.

If those don't appeal to you, you could try more of a tour of the Dakotas, and see western Montana. If you want to go the 2 lane route, you could take US 14 and follow the Little House on the Prairie Route (See the middle link from AZ Buck's advice for someone else who recently took that trip), then cut down into Badlands NP and over into the Black Hills stopping at Custer State Park. From there head into Wyoming, stopping by Devils Tower, before taking the backroads north into Montana. Hop on I-94, and start heading back, taking a quick swing through Teddy Roosevelt NP before heading back home.