I love train travel. I think it's the best way to travel anywhere, and the US doesn't take advantage of it. However, Northwest Indiana has a great trainline to take you into Chicago. I've been traveling to Chicago this way for years and nothing beats it!
In Chicago, the best view of the city is from the John Hancock Tower. From the top you can see the Willis Tower, Navy Pier and Lake Michigan stretching to the horizon. But it's expensive! This is how you can get to the top without buying a ticket.
First time to the city? Returning on a tight schedule? Stopping by on a road trip? This city is the highlight of the Midwest in my opinion. Check out some of my top sights in Chi-town.