Yes, Amtrak offers service from Boston to Chicago, but it requires a connection from Maine.

How long is the drive?

The drive takes approximately 19 hours of pure driving time.

Are there direct flights?

No, there are no direct flights from Bangor to Chicago.

What is the best time to visit?

Summer and early fall offer the best weather for exploring the city.

Like any major city, stay aware of your surroundings in downtown areas.

Newport

Chicago

Flight Driving

Newport to Chicago

Updated: 30 May 2026

The journey from Newport, Maine, to Chicago, Illinois, covers approximately 1,200 miles. Driving involves taking I-95 South to I-90 West, which provides a direct path through Massachusetts, New York, and across the Great Lakes region. Flying from Bangor International Airport (BGR) to Chicago O'Hare (ORD) typically requires a connection. You will travel from the Atlantic coast through the industrial heartland of the Northeast and into the Midwest. This route is famous for its scenic drive through the Berkshires and along the shores of Lake Erie. Expect significant toll costs on the New York State Thruway.

Total Distance: 1,900 km driving distance; 1,600 km straight-line air distance.

Fastest Way

Flight from Bangor (BGR) to Chicago (ORD) takes 5 hours including layovers.

Cheapest Way

Driving is the most economical for groups.

Compare Newport to Chicago Routes

	Flight Connecting	Driving Direct
Duration	5 hours	19 hours
Avg Price	$200 - $450	$200 - $350 in fuel
Operator	United Airlines	Personal Vehicle
Route	BGR to ORD via EWR or IAD.	I-95 S to I-90 W.
Tip	O'Hare is a major hub, offering many connection options.	The New York State Thruway is the most efficient path but includes tolls.

Travel Tips

Tolls
Use an E-ZPass to save time and money on the I-90 toll roads.
Traffic
Avoid driving into Chicago during the morning and evening rush hours.
Parking
Use public transit or parking apps to find affordable spots in downtown Chicago.
Weather
Be prepared for sudden weather changes near the Great Lakes.
Booking
Book your Chicago hotel in advance to secure better rates.

Safety Tips

Winter Driving
Be extremely cautious of lake-effect snow on I-90 during winter months.
Vehicle Prep
Check your lights and wipers before the long drive.
Emergency Kit
Keep a winter emergency kit in your car at all times.
Navigation
Use a reliable GPS to navigate the complex highway interchanges in Chicago.