There are several ways but one of the best routes for driving to Virginia Beach from Chicago is via Pittsburgh by way of Washington DC, but this route is really stressful because of the PA Turnpike. It's best to drive through Morgantown (WV) and Hagerstown (MD) down I-81 toward Charlottesville (along I-64). Then, Richmond to Newport News and Virginia Beach. That's probably the most scenic and easiest option to get to Virginia Beach from Chicago.
I have done this trip a couple of times passing through Frederick MD..it's about 900 miles. Try avoiding DC by taking US 15 south from Frederick, entering Virginia, and staying on US 15 south all the way past I-66 to US 29 south.
You can also bus it to Virginia Beach. These are the companies that travel from Chicago to Virginia Beach or that have stops in the vicinity of Virginia Beach: Amtrak Thruway Motorcoach, Coach USA, Dillon's Bus Service, First Transit, Greyhound, Megabus, MV Transportation, Home Ride and Pike Ride.