Find coaches from Portland, OR to Chicago

Next bus departures

Next departures from Portland to Chicago on 13 November
Operated byVehicle typeDeparture timeDeparture locationTrip durationArrival timeArrival locationRecommendedPrice and booking link
Greyhound Lines, Inc. + FlixBus
Bus
Portland Curbside Bus Stop
Chicago 95Th & Dan RyanCheapest
Greyhound Lines, Inc.Bus
Portland Curbside Bus Stop
Downtown Greyhound StationFastest
Greyhound Lines, Inc.Bus
Portland Curbside Bus Stop
537-517 W. Jackson BlvdNo tags
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
537-517 W. Jackson BlvdNo tags

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

Compare 2 ways to travel 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 R 2 325, it presents an excellent value for a comfortable ride.

5train per day
2d 4hAverage duration
2823 kmDistance
257kgCO₂ emissions
Bus
Average priceR 1 956 - R 12 003Average duration3d 6h
71kg CO₂e
Train
Average priceR 2 325 - R 29 396Average duration2d 4h
257kg CO₂e

Frequently asked questions about travelling from Portland, OR to Chicago by bus

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

    The bus ticket price from Portland to Chicago starts at R 1 956. The best way to find cheap bus 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 bus ride from Portland to Chicago?

    The average travel time between Portland and Chicago is around 3d 6h, although the fastest bus will take about 2d 13h. This is the time it takes to travel the 2827 km that separates the two cities.

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

    The number of buses from Portland to Chicago can differ depending on the day of the week. On average, there are 7 on this route. Some buses run direct routes, while others have layovers. Simplify your bus trip from Portland to Chicago by comparing and selecting the bus that fits your travel style and budget on Busbud.

  4. Which bus companies travel from Portland to Chicago?

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

  5. What are the departure and arrival stations when taking the bus from Portland to Chicago?

    Buses travelling between Portland and Chicago leave from Portland Union Station or Portland Airport and arrive at Downtown Greyhound Station, Chicago O'Hare International Airport, Polk St & Canal St.

Find cheapest prices for buses

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

Best price found
10/11
R 6 710
11/11
R 5 799
Today
R 6 175
13/11
R 7 489
14/11
R 4 143
15/11
R 3 188
16/11
R 4 572
17/11
R 4 485
busbud logoThe cheapest trip from Portland, OR to Chicago was searched and found on 15 Nov 2025 with a price of R 3 188

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

You can expect to pay from R 3 188 to R 8 672 for a bus ticket from Portland, OR to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at R 3 188, which is on 2025-11-15.

What's the cheapest way to go from Portland, OR to Chicago?

busbud logoThe bus is the cheapest travel choice for this destination

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