Chicago, Illinois

The Willis Tower is something that should be on everyone’s Route 66 list. Although the name might not ring a bell. That's because it was formerly known as the Sears Tower.

Built in 1973, it became the tallest building in the Western hemisphere for 25 years until a new building at the World Trade Center in New York City overtook it.

Stop by the The Sky Deck on the 103rd floor where you can view the entire city from up above.

After that go on the ledge, which is underneath the Skydeck. This is a 1300 foot tall glass elevator that takes you outside of the building, and slowly down to the ground so you can see Chicago like never before.