What companies run services between Portland, OR and Chicago?

The following travel company offer services from Portland, OR to Chicago: Travel with Alaska Airlines to go to Chicago by plane. For a good deal on tickets, you can find Alaska Airlines Portland, OR to Chicago tickets on Omio for $176 (€157).

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How to travel from Portland, OR to Chicago

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Travel options
from Portland, OR to Chicago

How to get from Portland, OR to Chicago by train, bus or flight.

Our recommendation

The best way to travel from Portland, OR to Chicago is by taking a flight because it’s the best combination of price and speed.

06:40AM4h00

Portland, OR

06:40AMChicago

€1531One-way

0 transfers

Cheapest

06:40AM4h00

Portland, OR

06:40AMChicago

€1531One-way

0 transfers

Fastest

06:40AM4h00

Portland, OR

06:40AMChicago

€1531One-way

0 transfers

Other options

Bus

Flight

02:25AM88h50

Portland, OR

02:25AMChicago

€2751One-way

0 transfers

04:41AM12h51

Portland, OR

04:41AMChicago

€2251One-way

0 transfers

03:43AM13h19

Portland, OR

03:43AMChicago

€3351One-way

0 transfers

Find all the dates and times for this journey by train, bus, flight, and ferry .

Compare prices and tickets Prices for trains, buses and flights

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Travel Information to Chicago from Portland, OR

	Distance	1750 miles (2822 km)
	Available travel modes	Flight
	Fastest mode	Flight • $176 (€157) • 4 h 24 min
	Popular travel companies	Alaska Airlines

Travel 1750 miles (2822 km) by flight to Chicago from Portland, OR. Alaska Airlines is the main travel company operating this journey. Travelers can even take a direct from Portland, OR to Chicago.

More than 1,000 travel companies trust us to sell their tickets all in one place.

All travel companies: Airlines and Train from Portland, OR to Chicago

You can travel by train or flight for as low as $64 (€57). When you search for schedules and tickets, Omio will show you the best trip.

Train Companies

Airlines

Amtrak is the main travel company in the United States and operates medium and long-distance intercity services in 46 American states and 3 Canadian provinces. With over 300 Amtrak travel running daily, you can travel by travel across America and explore destinations near and far. Take the Acela travel for high-speed services connecting popular cities in the Northeast, the Coast Starlight to travel up and down the stunning West Coast or the Empire Builder to travel from Chicago to the Midwest and the Pacific Northwest among others. Amtrak offers different class options to suit any traveler’s budget with classes like Coach, Business, First and the Sleeper Class, where you can book a Roomette, Bedroom, and Bedroom suite among others for night travel. When you book your travel journey from Portland, OR to Chicago, you can choose between ticket types like Saver, Value, Flexible, Business and Premium.

American Airlines is one of the leading airlines in the USA and the world; they offer Main Cabin, Business and First Class tickets for your travel to Chicago from Portland, OR.

FAQs: Travel from Portland, OR to Chicago

FAQs: Travel to Chicago easily. Whether you want fast, cheap or something entirely different, our travel experts have collected everything you need to know so you can find the best option from Portland, OR to Chicago.

You can go from Portland, OR to Chicago by flight.

The distance from Portland, OR to Chicago is approximately 1750 miles (2822 km).

These are the most popular departure and arrival points when traveling from Portland, OR to Chicago:

The following travel company offer services from Portland, OR to Chicago:

Travel with Alaska Airlines to go to Chicago by plane. For a good deal on tickets, you can find Alaska Airlines Portland, OR to Chicago tickets on Omio for $176 (€157).

Looking to extend your trip from Portland, OR to Chicago? Many Omio customers who go from Portland, OR to Chicago usually extend their vacation to explore other popular destinations like New York City, Indianapolis, IN or Detroit, MI. If you're looking to explore New York City, Indianapolis, IN or Detroit, MI from Chicago, let Omio find you the best connections available at an affordable price.

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