Is the train worth it?

Yes, the scenery through the Rockies is spectacular.

How do I get to Seattle?

Take the Whidbey Island ferry or drive south on I-5.

Are there direct flights?

Yes, multiple airlines offer direct flights from SEA to ORD.

What is the best time to visit?

Late spring and early fall offer the most pleasant weather.

Like any major city, it is safe if you stay in tourist-friendly areas.

Anacortes

Chicago

Train Flight

Anacortes to Chicago

Updated: 30 May 2026

To reach Chicago from Anacortes, you must first travel to Seattle. From there, you can take the iconic Amtrak Empire Builder train, which offers a stunning 46-hour journey across the northern United States. Alternatively, you can fly from Seattle-Tacoma International Airport (SEA) to O'Hare (ORD) or Midway (MDW) in about 4 hours. This route connects the Pacific Northwest with the heart of the Midwest.

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

Fastest Way

Flying from SEA to ORD takes only 4 hours of flight time.

Cheapest Way

Flying is often cheaper and significantly faster than the train.

Compare Anacortes to Chicago Routes

	Train Direct	Flight Direct
Duration	46 hours	4 hours
Avg Price	$200-$600	$250-$500
Operator	Amtrak Empire Builder	Alaska Airlines / United
Route	Seattle King Street Station to Chicago Union Station.	SEA to ORD.
Tip	Book a sleeper car for a comfortable multi-day experience.	Take the Light Rail from downtown Seattle to the airport.

Travel Tips

Train Booking
Book your Amtrak tickets months in advance for the best prices.
Airport Transit
Use the Link Light Rail to get from Seattle to the airport efficiently.
Packing
Chicago weather is unpredictable; bring layers regardless of the season.
Dining
Don't leave without trying authentic Chicago-style deep-dish pizza.
Safety
Stay aware of your surroundings in busy tourist areas like the Loop.

Safety Tips

Train Safety
Keep your belongings secure in your sleeper cabin at all times.
Airport Security
Arrive at SEA at least 2 hours before your domestic flight.
City Safety
Stick to well-lit, populated streets when walking at night.
Health
Stay hydrated during the long train ride to avoid altitude-related fatigue.