Is there a train to Chicago?

Yes, you can take an Amtrak train from DC to Chicago.

Expect to pay $30-$60 in tolls for a round trip.

Is the flight better?

Yes, it avoids the stress of driving and traffic.

Where does the flight arrive?

Flights arrive at O'Hare International Airport.

How long is the drive?

Usually 12 hours, but traffic can easily double this.

Annapolis

Chicago

Flight Driving

Annapolis to Chicago

Updated: 28 May 2026

The trip from Annapolis to Chicago is approximately 700 miles. You can drive via I-70 West to I-80 West, which takes about 11 to 13 hours. Alternatively, you can fly from BWI Airport to O'Hare International Airport. Chicago is a major cultural and economic hub known for its architecture, museums, and vibrant food scene.

Total Distance: Driving distance 1,126 km, straight-line air distance 950 km.

Fastest Way

Flying is the fastest method, taking about 2 hours in the air.

Cheapest Way

Flying is often the most cost-effective and fastest way to reach Chicago.

Compare Annapolis to Chicago Routes

	Flight Direct	Driving Direct
Duration	2 hours	12 hours
Avg Price	$150 - $350	$150 - $250 in fuel
Operator	United Airlines	Personal Vehicle
Route	BWI to ORD.	I-70 W to I-80 W through Pennsylvania, Ohio, and Indiana.
Tip	Flying is significantly faster and often cheaper than driving.	Be prepared for heavy traffic and multiple tolls along the entire route.

Travel Tips

Tolls
Use E-ZPass to handle the many tolls on the I-80 corridor.
Parking
Parking in Chicago is expensive; use parking apps to find better rates.
Public Transit
Use the 'L' (Chicago Subway) to get around the city quickly and cheaply.
Walking
Chicago is best explored on foot; bring comfortable walking shoes.
Booking
Book your flights well in advance to get the best prices.

Safety Tips

Traffic
Be extremely cautious when driving in Chicago traffic; it is aggressive.
Personal Safety
Stay aware of your surroundings in crowded tourist areas.
Emergency
Keep emergency numbers saved and know the location of your hotel.
Public Transit Safety
Stick to well-lit 'L' stations at night.