How far is Chicago from Sisters?

It is approximately 3,000 kilometers by road.

Is there a direct flight?

No, you must connect through a hub like Denver or San Francisco.

How long is the train ride?

The Amtrak Empire Builder takes about 46 hours from Portland.

What is the best way to travel?

Flying is best for time, while the train is best for scenery.

Do I need a car in Chicago?

No, Chicago has an excellent public transportation system.

Sisters

Chicago

Train Flight

Sisters to Chicago

Updated: 28 May 2026

Traveling from Sisters to Chicago requires a multi-modal approach. You will first drive 20 minutes to Redmond Municipal Airport (RDM) for a connecting flight to Chicago O'Hare (ORD). Alternatively, you can drive to Portland (PDX) to catch the Amtrak Empire Builder, which offers a scenic, multi-day rail journey to Chicago Union Station. Flying is significantly faster, while the train provides a unique cross-country experience. Chicago is a major transit hub, making it accessible from most regional airports.

Total Distance: 3,000 km driving distance, 2,700 km straight-line air distance.

Fastest Way

Flying from Redmond (RDM) to Chicago (ORD) is the fastest, taking roughly 6 hours total.

Cheapest Way

Amtrak coach seating is often the cheapest option if booked well in advance.

Compare Sisters to Chicago Routes

	Train Direct from Portland	Flight Connecting
Duration	46 hours	6 hours
Avg Price	$250-$500	$350-$600
Operator	Amtrak Empire Builder	United Airlines
Route	Portland Union Station to Chicago Union Station.	RDM to ORD via Denver or San Francisco.
Tip	Book a sleeper car for a more comfortable long-haul experience.	Book at least three weeks in advance for the best fares.

Travel Tips

Airport Choice
Use Redmond (RDM) for convenience, but check Portland (PDX) for more direct flight options.
Train Comfort
Bring a blanket and noise-canceling headphones for the long Amtrak journey.
Chicago Transit
Use the 'L' train system to get around Chicago; it is faster than driving in city traffic.
Dining
Try deep-dish pizza at a local institution like Lou Malnati's or Giordano's.
Weather Prep
Chicago weather changes rapidly; always carry a light jacket even in summer.

Safety Tips

Urban Awareness
Stay alert in crowded tourist areas and keep your belongings secure.
Public Transit
Stick to well-lit, populated stations when using the 'L' at night.
Ride-sharing
Use reputable apps like Uber or Lyft when traveling late at night.
Emergency Numbers
Keep the local emergency number saved in your phone.