How long does it take to fly?

The flight time is about 4 hours and 30 minutes.

Is the train ride worth it?

The train ride is very scenic but takes about 46 hours.

What is the best way to travel?

Flying is the fastest and most practical way.

Are there direct flights?

Yes, there are direct flights from Portland (PDX) to Chicago (ORD).

How do I get to the train station?

You will need to drive or take a shuttle to Portland Union Station.

Tillamook

Chicago

Train Flight

Tillamook to Chicago

Updated: 28 May 2026

The journey from Tillamook to Chicago spans over 3,000 kilometers. The most practical way to travel is by driving to Portland (PDX) and taking a flight to Chicago (ORD or MDW). Alternatively, you can take a train from Portland on the Empire Builder line. This is a major cross-country journey requiring significant planning.

Total Distance: 3,300 km driving distance; 2,800 km straight-line air distance.

Fastest Way

Flying from Portland (PDX) is the fastest way to reach Chicago.

Cheapest Way

Booking a flight in advance is often cheaper than a sleeper train.

Compare Tillamook to Chicago Routes

	Train Direct from Portland	Flight Direct from PDX
Duration	46 hours	4 hours 30 mins (flight time)
Avg Price	$200-$500	$300-$600
Operator	Amtrak Empire Builder	United Airlines, Alaska Airlines
Route	Drive to Portland Union Station, take train to Chicago Union Station.	Drive to PDX, fly to ORD.
Tip	The train journey is scenic but very long.	Book flights well in advance for better prices.