Is it better to fly or drive?

Flying is much faster, but driving allows for a scenic trip through the Midwest.

How long is the flight?

The flight time is approximately 2 hours.

Yes, there are many toll roads in the Midwest.

What is the best route?

I-65 North is the primary highway for this trip.

Yes, it is a standard interstate route.

Winston-Salem

Chicago

Flight Driving

Winston-Salem to Chicago

Updated: 28 May 2026

The distance from Winston-Salem to Chicago is approximately 700 miles. You can drive via I-77 and I-65, which takes about 11-12 hours, or fly from Piedmont Triad International Airport (GSO) to Chicago O'Hare International Airport (ORD). Flying is significantly faster, with a flight time of about 2 hours, while driving is a long-haul journey that requires careful planning.

Total Distance: 1,130 km driving distance; 950 km straight-line air distance.

Fastest Way

Flying is the fastest method, with a total travel time of about 5 hours including airport procedures.

Cheapest Way

Driving is generally cheaper for groups, while flying is more cost-effective for solo travelers.

Compare Winston-Salem to Chicago Routes

	Flight Connecting	Driving Direct
Duration	2 hours	11 hours 30 mins
Avg Price	$150-$350	$130-$170 in fuel
Operator	American Airlines / United	Personal Vehicle
Route	GSO to ORD	I-77 N to I-65 N
Tip	Book early to secure the best rates for this popular route.	Plan an overnight stop in the Louisville or Indianapolis area.

Travel Tips

Traffic
Chicago traffic can be heavy; use public transit (the L) whenever possible.
Parking
Parking in Chicago is very expensive; use public transit or ride-sharing services.
Walking
Chicago is a very walkable city; bring comfortable shoes.
Weather
Be prepared for cold weather if traveling during the winter months.
Safety
Stay in well-lit, populated areas, especially at night.