Oak Park to Leesburg: Route 66 to DC Suburbs Road Trip

Departing from Oak Park, Illinois—home to Frank Lloyd Wright's Prairie School masterpieces—you'll traverse 700 miles east to Leesburg, Virginia, a historic town in the DC exurbs. This route parallels the old National Road (US 40) and crosses the Appalachian Mountains via the scenic I-70 corridor through Maryland.

Your journey typically takes 10.5 to 12 hours of pure driving, but plan for a full day with rests. The reward: a transition from Midwestern flatlands to rolling Piedmont hills, with distinct regional cultures in between.

Crossing the Allegheny Mountains, you'll encounter the Chesapeake & Ohio Canal National Historical Park near Hancock, Maryland—a serene detour for hiking or biking along the old towpath. Further east, the Appalachian Trail intersects the route near Harpers Ferry, West Virginia, a UNESCO World Heritage Site (part of the Appalachian Trail system) renowned for its Civil War history.

In Ohio, the flat farmland gives way to rolling hills, and you'll pass through the Amish country around Millersburg, where you can buy handmade cheeses and quilts at local markets.

Culinary infrastructure is robust: From Chicago-style deep dish in Oak Park to Pennsylvania Dutch shoofly pie in Lancaster, the route offers regional specialties. Chain restaurants dominate at exits, but local diners like the Dutch Cupboard in Bedford, PA, provide authentic fare.

For a deeper dive into discovering unusual stops, check out how to find the best stops and hidden gems between cities.

Fatigue is a major concern on long drives; plan to stop every two hours or so. The I-70 corridor has numerous rest areas in Ohio and Pennsylvania, like the Beaver Creek Rest Area near Columbus, offering picnic tables and restrooms.

• Family-friendly stops: The Children's Museum of Indianapolis is a 3-hour detour, but a 1-hour detour to the Ohio Caverns near West Liberty offers guided tours suitable for kids.
• Pet-friendly framework: Most hotels along the route allow pets; many rest areas have designated pet exercise areas.

Hidden off-route spots: Bicycle Heaven in Pittsburgh (a quirky museum) and the Flight 93 National Memorial in Shanksville, PA, are poignant and unique.

Weather-wise, expect hot summers and cold winters; spring brings thunderstorms, and fall foliage peaks in mid-October through the mountains. Check forecasts before departure.

Your primary path follows I-90 east from Chicago to the Indiana Toll Road, then I-80/I-90 across Ohio and Pennsylvania, before picking up I-70 in Hancock, Maryland, and finally I-270 south toward Leesburg. This route is well-maintained, with ample fuel stations and services.

• Fuel costs: Expect $90–$120 for a sedan, depending on fuel efficiency and current gas prices.
• Tolls: The Indiana Toll Road costs about $20 for a passenger car; the Pennsylvania Turnpike adds $40–$60.
• Road quality: Excellent on interstates; watch for construction zones in Ohio and Pennsylvania.

For real-time traffic and road conditions, dial 511 or use state DOT apps. The route is generally safe, but be prepared for mountain grades in Pennsylvania and Maryland.

If you're wondering is it worth driving Oak Park, IL to Leesburg, VA, the answer is a resounding yes—the journey offers diverse landscapes and hidden gems.