Is flying better than driving?

Yes, flying is much faster and less exhausting for this distance.

How much is parking in Chicago?

Expect to pay 30 to 50 dollars per day in downtown garages.

Yes, there are many tolls on the highways; use an I-PASS or E-ZPass.

How long is the flight?

Approximately 2.5 hours from Norfolk.

Yes, Amtrak offers service, but it is very slow and requires a transfer.

Chesapeake

Chicago

Flight Driving

Chesapeake to Chicago

Updated: 28 May 2026

The journey from Chesapeake to Chicago covers 1,200 kilometers. By car, the trip takes 13 to 15 hours via I-64 and I-65, which is a long-distance drive. Alternatively, you can fly from Norfolk International Airport (ORF) to O'Hare International Airport (ORD) or Midway (MDW), which is much faster. Chicago is a major city known for its architecture, museums, and deep-dish pizza. Planning your travel mode is critical for this long-distance trip.

Total Distance: 1,200 km driving, 1,050 km air distance.

Fastest Way

Flying is the fastest method, taking only 2.5 hours in the air.

Cheapest Way

Driving is cheaper for groups, while flying is much faster for solo travelers.

Compare Chesapeake to Chicago Routes

	Flight Direct	Driving Direct
Duration	2.5 hours	14 hours
Avg Price	150-300 USD	130-200 USD
Operator	United/American Airlines	Personal Vehicle
Route	ORF to ORD/MDW.	I-64 to I-65 North.
Tip	Book flights in advance to secure lower fares.	This is a very long drive; plan for at least one overnight stop.

Travel Tips

Flight Advantage
Flying saves you a full day of driving; use the Norfolk airport for convenience.
Driving Strategy
If driving, plan for at least one overnight stop in Kentucky or Indiana.
Car Rental
If you fly, you will likely need to use public transit or ride-sharing in Chicago.
Architecture
Take an architecture boat tour to see the city's famous skyline from the river.
Weather
Chicago winters are very cold; pack warm clothing if traveling in winter.