What’s it like driving between Washington, DC and Chicago? What types of roads, scenery, etc. do you find? If you’ve driven a similar long-haul route, such as Chicago to Baltimore, I’d also love to hear your take.
I’ve always flown - I’ve never driven this route.
I live about half-way between, and have driven several times to each of Chicago and DC.
The roads are good all the way, though they can be very crowded at both ends, around Chicago and around DC.
The scenery can be divided into two parts: Appalachia (western Pennsylvania, western Maryland, West Virginia and southwestern Ohio) and Mid West (the rest of Ohio and Indiana). Appalachia can get quite mountainous, and always has interesting scenery; the Mid West is flat, and mostly corn fields and soybean fields.
You could drive on the interstates, and miss a lot of the interesting parts, or you could drive on the main roads, and see the towns and cities on the way. Here’s my suggestion for avoiding the interstates: US 50 to Athens OH (which will take you through scenic West Virginia), US 33 to Fort Wayne IN, and US 30 to the outskirts of Chicago. That route is all good to very good roads, with four-lanes for about 70% of the distance – and US 33 and US 30 is my favourite way of driving to Chicago from here.
Too late to edit: I meant that southeastern Ohio is part of Appalachia.
Ohio can be tough if you aren’t used to it; especially on Rte 30 or anything north. Its straight, flat, and pretty but also pretty much the same. If you are doing the trip in one shot/day, be aware of highway hypnosis.
Then you cross the border into Indiana, and – more of the same. 
I driven from southern and central Virginia to Michigan several times. Once with two cats who cried for the entire 10 hour trip.
Virginia: I use 522 (Zachary Taylor highway) N, which if I were coming from DC, I would pick up in Front Royal off of 66. This is a very pretty drive. The speed limit is slower, but since it is more direct than the interstates, time-wise it’s a wash, so I choose the prettier route. It pretty much joins 70N when it crosses into PA, then I get on the PA Turnpike at Breezewood.
Pennsylvania: traffic is bad, the driving can be harrowing depending on what you’re used to, because of frequent construction resulting in narrow lanes on mountain highways and really short on-off ramps. I always gas up & get food in Breezewood, so I wont have to get on or off anything in Pennsylvania, but I can get alarmed easily while driving. Parts are very pretty. Follow 76/70 (PA Turnpike) till they split, then follow 76 to Ohio, pick up 80 in Ohio (Ohio Turnpike).
Ohio: snoooooooze. Oh MY GOD its boring. Stab-yourself-in-the-face-just-for-something-to-do boring.
ETA: I have done the rte 50 once - it IS pretty – really pretty – BUT it takes FOREVER. Also it is very hilly, if you have any question about your car’s brakes or transmission – don’t do it.
I live in Madison, WI and hail from Columbia, MD…so I’m pretty familiar with the trip. Habe driven it 10 or 12 times over the years There are two basic routes:
Turnpike Hell: quicker, less fun. Basically Chicago --> Ohio TP --> Pennsylvania TP and down through PA in MD…I’d probably come down I70 and then pick up 270 to Rockville/DC
Just Drive: longer, more scenic. For me, I head south to Bloomington, IL and hang a left to Indy. You’d probably head south from Chicago directly to Indy (65–>70) through Columbus and then head south just after Wheeling, WV (79 --> 68) to Morgantown. This route takes 68 due east, then joins 70. From there, either 270 S to DC or 695–>95 S to Columbia/B’more/Annapolis depending on final.
Lotsa tolls and shitty roads on the northern route, about 90 minutes more travel time on the southern route. Madtown > Charm City usually takes me 13-14 hrs, you’re looking at 11-12. PLAN your route to account for rush hours and peak travel. DC and Chi rush SUCKS, and you can get screwed up in Columbus, Indy and Dayton.
I live in the Chicago suburbs and my wife’s family is in the DC suburbs (Alexandria area).
It was a 13 hour drive (with breaks) and from Illinois to Pennsylvania is a whole lot of flat farmland. This didn’t bother me too much as basically everything outside of the city & burbs is flat farmland so I’m used to it but it sure isn’t entertaining.
Hitting Pennsylvania was nicer with some hills then the mountains. Pittsburgh coming from the west was actually rather picturesque (the view returning wasn’t so much; I don’t recall if we took a different road or what). The mountain tunnels were pretty cool for a flatlander like myself.
Virginia was green and rolling, reminding me somewhat of lower Michigan. Small towns and farms but with more landscape than downstate Illinois (or Indiana or Ohio).
It wasn’t a bad trip aside from a sick kid in the car. No real traffic issues until we hit the DC area. I’d do it again without any qualms but I wouldn’t exactly look forward to it.
Have done it a few times; not much to add beyond what others have said. The eastern part of the drive can be fairly scenic (hills, mountains, some forests); the western part is largely flat farmland. Traffic is likely to stink at both endpoints.
Not terribly exciting, really. Most of the route is turnpike - good roads, but limited exits and of course there are the rest areas that have the assorted so-so food for the captive audience.
The tunnels in western PA are sort of interesting - I’d been through them as a very young child and thought they were cool even back then.
Having a screaming infant in the back seat (as we did) both slows down and speeds up your trip. When the baby screams, you press that much harder on the gas pedal out of frustration / annoyance / the need to get to the next rest stop to see what she’s screaming about. But then you have the rest stop… which eats up all your time savings :smack:.
All in all, I don’t recommend that sort of driving accessory :).
As a service to out of state folks we have a division of specialists who will pop out of nowhere with flashy lights to keep you alert. Keep your speed down and do not feed the bears.
Breezewood, PA. Saddest town in the USA.