Driving directly from Cincinnati to Iowa we take highway 74 through Indianapolis, Bloomington IL, Peoria, and into Rock Island where you pick up highway 80. It is a total of 550 miles from our house in NE Cincinnati to Grinnell. My favorite mapping program is

(Got cut off) www.mapblast.com. The driving times are most realistic, and then add times for your own number of stops.

The older I get, the LESS I like driving if I actually want to "get somewhere"! I'm now the ripe old age of 35 and prefer to fly whenever possible mainly because U.S. interstates are quite variable in quality and congestion, trucks and RVs can make for a harrowing trip and nasty bathrooms in a Stuckey's just isn't that appealing anymore. Last month we waited too late and couldn't get airline seats between New Orleans (home) and Houston so we drove. Result: my car has a broken windshield (thank you Tyson's Chicken truck) and a big paint chip missing in the hood (compliments of a USPS truck). Oh, and let's not forgot the long stretches of "road construction" on busy I-10 where the road is down to one lane...and there is NO construction equipment or workers to be found!

I'd LOVE to do a "backroads" leisurely drive one day, though...I just need to find the right place to do it!

Jay - I think the idea is wonderful and even though along the way you may encounter a few hair pulling moments, years from now you, your wife and especially your daughter will look back on the vacation with fond memories. When I was younger, those were the only kinds of vacations my parents and I took. Now with a husband in the military, we move a lot and make the transfers into "mini vacations" as well.

As far as suggestions for Chicago, I can relate to the "relatives are like French cheese" comment. ;-) But there are so many things to see there, that if you could spend a few extra days there, it would be well worth it. Your daughter would definitely enjoy the Shedd Aquarium, Lincoln and/or Brookfield Zoo. If she (or you and wife) aren't afraid of heights, a trip to the top of the Sears Tower would be a breathtaking treat.

In Indiana, it would take you out of your way a bit (east on route 6 to the town of Nappanee, about 2 hours from I-65), but a place called Amish Acres is a step back in time - nice farm land along the way, yummy homemade food, unique handmade gifts at the shops, etc. I do think there's a comparable community somewhere in Iowa off of I-80, though, so you may already know about the Amish.

You brought back major memories with the mention of Stuckey's stops! The last time I took the I-80 route across Indiana, Illinois and Iowa, I saw them, but that's been several years ago.

Ditto to the walk-a-bility of Indianapolis and the suggestions already posted for that city.

Have fun planning your vacation! Take along plenty of things to keep your daughter occupied in the car and take lots of mini breaks and you'll all be fine!

P.S. A side note to Patrick - Your U.S./Canada trip plans sound wonderful. I've been reading with pleasure your posts on the Europe board about your recent time there. If I may ask, what do you do for a living that you can take so much time off? I'm incredibly jealous! Enjoy your planning, as well!

Got for it!! Who cares what your friends think? I bet you'll be the envy of every one of them. There is a whole big, beautiful country out there waiting to be explored.

On a trip from Ann Arbor to Denver, my children and I were able to stop at a restored pony express station in Nebraska. My 7th grader had just studied it the previous year.

I think you have more options open to you when you drive.
Go and have fun!!

Sounds like a lot of fun. I'd make sure you pack a lot of books, etc. for your daughter. You are right about keeping your schedule loose. No use passing up that one site you'll never get a chance to see again.