New York to Chicago to Houston – what to see in-between?

Hi, all!

In October , I am going to the US for the first time for about a month, possibly more. It appears to be cheapest to fly to New York from London, a place that I have always wanted to visit.

After three or four days in N.Y., I need to go to Chicago to see a friend and the fact Chicago is another place I have always wanted to visit . Then I also have a friend in Houston. From Houston, I’ll likely fly back to London towards the end of the month.

I want to know whether there are places I should visit in-between Chicago and Houston that would be worthwhile. I am more of an urban traveller, I love cities, coffee/food but also love walking and would happily walk anywhere. Preferable transport would be a trains or an overnight bus rather than flying .

I’m not really focused too much on the budget as I have been saving up for a while. For Chicago and Houston, I will stay with my friends and then for the rest of the journey I plan to stay in a variety of places from AirBnB to hotels to motels. I don’t really drink either, which should save a considerable amount of money.

If you have any suggestions, please let me know! Thank you!

New York to Chicago to Houston – what to see in-between?