Amtrak's Empire Builder runs from Chicago to Portland.

How long is the drive?

It is a 45-hour drive covering 4,700 kilometers.

What is the best airport?

Portland International Airport (PDX) is the main hub.

Is Portland walkable?

Yes, the city is very pedestrian and bike-friendly.

What is the weather like?

Mild and rainy for most of the year.

Middletown

Portland

Flight Driving

Middletown to Portland

Updated: 28 May 2026

The journey from Middletown to Portland is a cross-country trip of approximately 4,700 kilometers. Flying is the most practical option, typically involving a connection in a major hub like Chicago, Denver, or San Francisco. Driving is a massive undertaking, usually taking 4-5 days along I-80 and I-84. Portland is known for its lush greenery, coffee culture, and proximity to the Pacific Coast. Prepare for a significant time zone change.

Total Distance: Driving distance 4,700 km; straight-line air distance 4,000 km.

Fastest Way

Flight from Newark (EWR) to Portland (PDX) is the fastest.

Cheapest Way

Driving is only cheaper if you have a large group to split fuel costs.

Compare Middletown to Portland Routes

	Flight Connecting	Driving Direct
Duration	8 hours	45 hours
Avg Price	$450 - $900	$500 - $800 in fuel
Operator	Alaska Airlines	Personal Vehicle
Route	EWR to PDX	I-80 W to I-84 W
Tip	PDX is an easy airport to navigate with great light rail access.	This is a major road trip; plan stops in Chicago, Denver, and Boise.

Travel Tips

Public Transit
Use the MAX Light Rail to get around the city without a car.
Coffee
Portland is famous for its coffee; visit local roasters in the Pearl District.
Rain
Pack a waterproof jacket as it rains frequently, even in summer.
Tax
Enjoy tax-free shopping throughout the state of Oregon.
Day Trips
Drive to the Columbia River Gorge to see Multnomah Falls.

Safety Tips

Driving
Be prepared for mountain driving on I-84 through the Blue Mountains.
Urban Safety
Be aware of your surroundings in downtown areas at night.
Emergency Prep
Carry tire chains if traveling in the Pacific Northwest during winter.
Navigation
Download offline maps as cell service can be spotty in remote areas.