Houston to Chicago

We are planning our first family roadtrip over July 4th week. I'm looking for fun family side trips to make the drive more fun. Places to stop or just really great scenery. DH and I will be traveling with a couple of 13 year olds and an 8 month old. Any suggestions would be appreciated. I think we will stay overnight once on the way there and once on the way back.

I was thinking that we would drive longer the first day....but I would like to stay over night someplace where we could maybe do something fun before getting started the next day.

Welcome aboard the RoadTrip America Forums!

Houston to Chicago is just 1100 miles by the most direct route possible, and a large chunk of that is on US-59 through many small towns in east Texas. To be honest, I don't see where you're going to find time for 'fun' stops along the way if you plan to make this drive in only 2 days. You might be able to make use of some state parks near the highways for picnic lunches and a little time for the kids to blow off some steam, but that's going to be about it. I would try to stop at least twice a day for some out-of-car time. Similarly, your halfway point is roughly in the Bootheel region of Missouri, a lovely area but not exactly a tourist mecca. I wish I could be of more help, but the reality of your time constraints limits what you can do and where you have to be when.

AZBuck

It goes right by Jefferson, Texas. See this post about my trip to Jefferson a few years ago. There were lots of people there with kids. I even picked up a twelve year old stalker for a while.

I actually really enjoy driving Highway 59 when I get the opportunity. It's on my list of Highways I'd like to explore further.

I don't know about the rest of Texas, but East Texas has really bought into the Main Street program the state has been trying and many of the towns are attempting to become tourist attractions as I found on this roadtrip.

It should at least give you some places to get out of the car and stretch your legs. A lot of the towns are introducing cute little restaurants and shops.

Have fun!