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.