Choosing Landmarks to Visit on a Road Trip

If you haven't decided where to head north, I'd suggest doing so somewhere around the Mississippi. If you are serious about going to Springfield, IL, you could head up I-39 and that will take you within a few minutes of Starved Rock, near Utica, IL.. From there you have two main choices as I see it. One, head on up I-39 to Route 20, and take Route 20 into Galena, IL. It's a very historic town that is fairly charming, especially for a short visit. There are some great shops, some with local artists/photographers work on display, others with local food items, a couple wine/beer places, etc. Some of the historic homes and buildings (including Pres. Grant's home). From Galena it is a short ride over to the "Field of Dreams" that the_jazz mentioned, and you can head north into MN from that point.

Alternatively, from Starved Rock area you can head west on I-80. You could stop in Clinton, IA, which has a historic downtown, some nice shops (though nowhere near what Galena has), and the shop from the "American Pickers" TV show. You can follow the river north from Clinton, still make the stop in Galena and "Field of Dreams", and head on your way up into MN. As far as the stretch in Northern IL and along the MI, those would be my suggestions.

 

As far as coverage goes, I have AT&T and when we passed through South Dakota and Montana in 2010, there was zero reception for a good 500+ miles of our journey. Checking those coverage maps are crucial when you're driving through vast swaths of unfamiliar highway alone.

 

Levite's over the top indictment of Wall Drug is uh... absolutely correct.

About ten years ago, a friend and I (and a couple hundred others) spent a lovely January night and most of the next day on the floor of the National Guard Armory in Ogallala, Nebraska after they closed I-80 during a blizzard.
Also, buy a pair of tire chains before you leave home. There may be passes in the Rockies, even on Interstates, where they will require you to use tire chains. And have a roadblock to enforce it. And there will be "friendly" locals selling chains for probably four times what they would cost you in Columbus.

From Ogden you will go through 300-400 miles of mountains before you get to what passes for (but really isn't) the flat part. Blizzards are maybe actually worse on the high plains than in the mountains.

I used to structure my frequent road trips from Boston to Dodge City based on avoiding Chicago at rush hours.
Or, from Springfield you could head West. There's a beautifully graceful bridge on I-72 about a hundred miles West of Springfield. And then Hannibal Lecter Missouri with a lot of Tom Sawyer and Mark Twain history. Then head North on The Great River Road, a well marked scenic byway that mostly hugs the Mississippi River, and also gets you to Dubuque and Minnesota.

Lindy
I wanna go on a road trip. Maybe in January.