Is it better to fly or drive?

Flying is much faster for this long distance.

How long is the drive?

The drive is approximately 14 hours.

What is the best airport?

O'Hare International Airport (ORD) is the main hub.

Yes, expect tolls on major highways in the Midwest.

Yes, tourist areas are generally safe, but remain aware of your surroundings.

South Boston

Chicago

Flight Driving

South Boston to Chicago

Updated: 28 May 2026

The journey from South Boston to Chicago is best made by flying from Raleigh-Durham International Airport (RDU) to O'Hare International Airport (ORD). Alternatively, you can drive, which takes about 13 to 14 hours via I-64 and I-65. Chicago is a major hub with excellent public transportation, making it easy to explore without a car. Be prepared for cold winters and windy conditions near Lake Michigan.

Total Distance: 1,200 km driving distance; 1,000 km straight-line air distance.

Fastest Way

Flying from RDU is the fastest way to reach Chicago.

Cheapest Way

Driving is cheaper for groups, but flying is much faster.

Compare South Boston to Chicago Routes

	Flight Direct from RDU	Driving Direct
Duration	2 hours 30 mins	14 hours
Avg Price	$180-$350	$150-$220 in fuel
Operator	United Airlines	Personal Vehicle
Route	RDU to ORD.	I-64 West to I-65 North.
Tip	Book early for the best fares.	Plan for an overnight stop to avoid fatigue.

Travel Tips

Public Transit
Use the 'L' train system to get around the city efficiently.
Weather
Dress in layers, as Chicago weather can change quickly.
Deep Dish Pizza
Try the famous Chicago-style deep dish pizza at a local restaurant.
Walking
Chicago is a very walkable city, especially in the downtown area.
Parking
Parking is expensive; use public transit whenever possible.