Bus Tickets from Portland, OR to Chicago

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TodayAug 18
from US$354
TomorrowAug 19
from US$293
WedAug 20
from US$276
ThuAug 21
from US$255
FriAug 22
from US$227
SatAug 23
from US$251
SunAug 24
from US$185
MonAug 25
from US$239

Cheap buses leaving tomorrow

One passenger / one way

  • This trip is recommended because it is the: Cheapest
    Departure time: August 19 at
    Departure city: Portland
    Departure location: Portland Curbside Bus Stop
    Arrival time: August 23 at
    Destination city: Chicago
    Destination location: Chicago 95Th & Dan Ryan
    Operated by: FlixBus + Greyhound Lines, Inc.
    FlixBus + Greyhound Lines, Inc.
    Vehicle: BusDuration:
  • This trip is recommended because it is the: Fastest
    Departure time: August 19 at
    Departure city: Portland
    Departure location: Portland Curbside Bus Stop
    Arrival time: August 22 at
    Destination city: Chicago
    Destination location: 537-517 W. Jackson Blvd
    Operated by: Greyhound Lines, Inc.Greyhound Lines, Inc.
    Vehicle: BusDuration:
  • Departure time: August 19 at
    Departure city: Portland
    Departure location: Portland Curbside Bus Stop
    Arrival time: August 23 at
    Destination city: Chicago
    Destination location: Downtown Greyhound Station
    Operated by: FlixBus + Greyhound Lines, Inc.
    FlixBus + Greyhound Lines, Inc.
    Vehicle: BusDuration:
  • Departure time: August 19 at
    Departure city: Portland
    Departure location: Portland Curbside Bus Stop
    Arrival time: August 22 at
    Destination city: Chicago
    Destination location: 537-517 W. Jackson Blvd
    Operated by: Greyhound Lines, Inc.Greyhound Lines, Inc.
    Vehicle: BusDuration:
  • Departure time: August 19 at
    Departure city: Portland
    Departure location: Portland Curbside Bus Stop
    Arrival time: August 23 at
    Destination city: Chicago
    Destination location: 537-517 W. Jackson Blvd
    Operated by: FlixBus + Greyhound Lines, Inc.
    FlixBus + Greyhound Lines, Inc.
    Vehicle: BusDuration:

Accepted payments

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Compare 2 ways to go from Portland to Chicago

Bus
Average PriceUS$123 - US$536Average Duration3d 7h
71kg CO₂e5 out of 5 stars
CheapestMost eco-friendly
Train
Average PriceUS$133 - US$1,780Average Duration2d 4h
257kg CO₂e1 out of 5 stars
Fastest
busbud logoBusbud recommends taking the train from Portland to Chicago

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 US$133, it presents an excellent value for a comfortable ride.

5train per day
2d 4hAverage Duration
US$133Cheapest ticket
257kgCO₂ emissions

Bus Portland, OR to Chicago: Trip Overview

Average Ticket PriceUS$210
Average Bus Trip Duration3d 7h
Number of daily buses6
Earliest bus departure1:00am
Distance2823 km
Latest bus departure8:00pm

Portland to Chicago Bus

Busbud shows you the best bus ticket fares and bus schedules so you can easily plan and book a trip by bus from Portland to Chicago.

We make sure you can find a bus service from Portland to Chicago from the most reliable bus companies operating this trip.

Discover how much the bus trip from Portland to Chicago will cost you. Use our filters and sorting features to find the cheapest bus tickets or luxury buses.

Frequently asked questions on the trip Portland, OR - Chicago

  1. What is the travel distance from Portland to Chicago?

    The distance between Portland and Chicago is around 2827 km (1753 miles).

  2. What are the departure and arrival locations for buses traveling from Portland to Chicago?

    Buses traveling this route start their trip at Portland Union Station, in Portland, and end it at Downtown Greyhound Station, in Chicago.

Find cheapest prices for buses

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

Best price found
08-16
US$484
08-17
US$482
Today
US$482
08-19
US$329
08-20
US$393
08-21
US$248
08-22
US$238
08-23
US$243
busbud logoThe cheapest trip from Portland, OR to Chicago was searched and found on Aug 22, 2025 with a price of US$238

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 US$238 to US$484 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 US$238 which is on 2025-08-22.

About Bus Travel

Bus Travel Tips

If you're abroad, study some local language. Not only could it get you out of a pickle during your bus trip from Portland to Chicago but it'll also be endearing to native speakers who will surely appreciate your effort.

Start sightseeing the minute your bus leaves the station. If you're on the night bus from Portland to Chicago, get comfy and count the stars.

Buses have one of the smallest carbon footprints of motorized transport modes. A bus going from Portland to Chicago will emit less CO2 than a car or an airplane.

Tune out to the fine sounds of your best music playlist on your bus trip from Portland to Chicago while indulging in miles on end of beautiful scenic views.

Did you know?

Did you know some bus companies in Germany offer to their passenger low-costs snacks and regional beer based on their destination? Prosit!

Did you know that 80% of the buses in North America are equipped with WiFi and power outlets ? And 60% of bus travellers have used their electronic device on board during 2014.

The bus driver with the longest career in the world drove more than 2,000,000 miles and is a happy World Record holder.

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

busbud logoThe bus is the cheapest travel choice for this destination

Will you be returning to Portland, OR by bus?

Bus from Portland, OR to Chicago

You can also go to Chicago by train

Train from Portland, OR to Chicago

Why choose Busbud?

The Best Way To Book Bus and Train Tickets

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