Train tickets from Portland, OR to Chicago

Next departures

Next departures for Portland to Chicago on November 13
Operated byVehicle typeDeparture timeDeparture locationTrip durationArrival timeArrival locationRecommendedPrice and booking link
Amtrak
Union Station
Chicago (Union Station), ILCheapestFastest
Amtrak
Union Station
Chicago (Union Station), ILNo tags
Amtrak
Union Station
Chicago (Union Station), ILNo tags
Amtrak
Union Station
Chicago (Union Station), ILNo tags
Amtrak
Union Station
Chicago (Union Station), ILNo tags
Amtrak
Union Station
Chicago (Union Station), ILNo tags
Amtrak
Union Station
Chicago (Union Station), ILNo tags
Amtrak
Union Station
Chicago (Union Station), ILNo tags

Last refresh of the prices: Yesterday at 7:35 PM PST.

Compare 2 ways to go from Portland to Chicago

We recommend taking the train

Among the sustainable travel choices, the train stands out as a good way to reach Chicago. The journey takes about 2 days, 4 hours 5 minutes, and with fares starting at just $191, it presents an excellent value for a comfortable ride.

5train per day
2d 4hAverage Duration
2823 kmDistance
257kgCO₂ emissions
Average Price$161 - $984Average Duration3d 6h
71kg CO₂e
Average Price$191 - $2,408Average Duration2d 4h
257kg CO₂e

Frequently asked questions on the trip Portland, OR - Chicago

  1. How much does a cheap train ticket from Portland to Chicago cost?

    The average train ticket price from Portland to Chicago is $339. The best way to find cheap train tickets from Portland to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!

  2. How long is the trip from Portland to Chicago?

    A train trip between Portland and Chicago is around 2d 4h, although the fastest train will take about 1d 22h. This is the time it takes to travel the 2827 km that separates the two cities.

  3. How many daily trains are there between Portland and Chicago?

    The number of trains from Portland to Chicago can differ depending on the day of the week. On average, there are 5. Some trains are direct while others include transferring trains. Simplify your train trip from Portland to Chicago by comparing and selecting the train that fits your travel style and budget on Busbud.

  4. Which train companies travel from Portland to Chicago?

    When taking the train from Portland to Chicago, you can travel comfortably and safely with Amtrak.

Find cheapest prices for trains

Price is for a one-way ticket for one passenger and based on past searches.

Best price found
11-10
$417
11-11
$510
Today
$520
11-13
$417
11-14
$417
11-15
$338
11-16
$417
11-17
$338
busbud logoThe cheapest trip from Portland, OR to Chicago was searched and found on Nov 15, 2025 with a price of $338

To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Portland, OR to Chicago, as early as possible.

You can expect to pay from $338 to $3,425 for a train ticket from Portland, OR to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $338 which is on 2025-11-15.

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