How to travel from Portland, OR to Chicago, IL

Mon, May 25
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1,000+ more
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Travel Information

Compare train, bus, and flight for Portland, OR to Chicago, IL

Omio recommends booking the train as it is the most popular option from Portland, OR to Chicago, IL among Omio's users. If you are prioritising price take the bus with prices starting from $136. For those with little time consider booking a flight which can get you there in 4h 17m. In case you are seeking to minimise your carbon footprint the train is your best bet as it emits only 0.8 - 2.5kg. The ticket price range depends on the travel mode: a bus costs an average of $136, and a train costs an average of $175.

Distance: 1754 miles (2823 km)

Compare train with

Most popular
Train
Flight
Bus
Driving

$403

Average price

$365

Average price

$321

Average price

Cheapest

$435

Average price

(fuel + tolls)

48h 5m

Average total duration

47h 35m

Onboard

+

30m

Additional time*

7h 17m

Average total duration

Fastest

4h 17m

Onboard

+

3h 0m

Additional time*

73h 20m

Average total duration

72h 50m

Onboard

+

30m

Additional time*

30h 52m

Average total duration

(door-to-door)

0.8 - 2.5kg

CO2 emissions

Lowest

8.5 - 16.9kg

CO2 emissions

2.8 - 7.1kg

CO2 emissions

-

CO2 emissions

Amtrak

Most popular train company

American Airlines

Most popular airline

Greyhound

Most popular bus company

Your own car or car rental

Direct Options

Direct Options

Direct Options

Direct Options

Additional time: Average total travel duration to departure point, security checks and transfers.

The cheapest way to travel from Portland, OR to Chicago, IL is a bus with an average price of $321 (€260).

This is compared to other travel options from Portland, OR to Chicago, IL:

A bus is $44 (€36) less than a flight for this route with tickets for a flight from Portland, OR to Chicago, IL costing on average $365 (€296).

A bus is $82 (€67) less than a train for this route with tickets for a train from Portland, OR to Chicago, IL costing on average $403 (€326).

The fastest way to travel from Portland, OR to Chicago, IL is by flight with an average journey time of 4h 17m.

Other travel options to Chicago, IL take longer:

Train takes on average 47h 35m.

Bus takes on average 72h 50m.

It's helpful to compare your options as there are 3 ways to travel between Portland, OR and Chicago, IL including taking a train, bus, and flight.
We recommend using the train as it is the most popular way to get from Portland, OR to Chicago, IL among Omio's users.

Travel options
from Portland, OR to Chicago, IL

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

Our recommendation

bus

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

  • FlixBusFlixBus+Greyhound · ·
    9:10 AM68h50
    Portland, NW Station Way (Station Place Parking Garage), OR
    8:00 AMChicago, Union Station (Amtrak), IL
    $1701One-way
    4 transfers

Cheapest

  • FlixBusFlixBus+Greyhound · ·
    9:10 AM68h50
    Portland, NW Station Way (Station Place Parking Garage), OR
    8:00 AMChicago, Union Station (Amtrak), IL
    $1701One-way
    4 transfers

Fastest

  • American AirlinesAA2977
    10:59 PM4h03
    Portland International Airport
    5:02 AMO'Hare International Airport
    $3421One-way
    0 transfers

Other options

  • Amtrak28 Empire Builder
    4:45 PM46h00
    Portland Union Station, Portland, OR
    4:45 PMChicago Union Station, Chicago, IL
    $3321One-way
    0 transfers
  • Amtrak500 Amtrak Cascades · 8 Empire Builder
    6:45 AM56h00
    Portland Union Station, Portland, OR
    4:45 PMChicago Union Station, Chicago, IL
    $3611One-way
    1 transfer
  • Amtrak28 Empire Builder · 1340 Borealis
    4:45 PM48h41
    Portland Union Station, Portland, OR
    7:26 PMChicago Union Station, Chicago, IL
    $3711One-way
    1 transfer
  • Greyhound · · ·
    1:50 AM60h35
    Portland, NW Station Way (Station Place Parking Garage), OR
    4:25 PMChicago, Greyhound Bus Station
    $1761One-way
    3 transfers
  • FlixBusFlixBus+Greyhound · ·
    8:00 PM78h20
    Portland, NW Station Way (Station Place Parking Garage), OR
    4:20 AMChicago, Greyhound Bus Station
    $2291One-way
    4 transfers
  • FlixBusFlixBus+Greyhound · ·
    8:00 PM82h00
    Portland, NW Station Way (Station Place Parking Garage), OR
    8:00 AMChicago, Union Station (Amtrak), IL
    $2611One-way
    4 transfers
  • American AirlinesAA2933
    6:15 AM4h16
    Portland International Airport
    12:31 PMO'Hare International Airport
    $3421One-way
    0 transfers
  • American AirlinesAA3303
    1:45 PM4h26
    Portland International Airport
    8:11 PMO'Hare International Airport
    $3421One-way
    0 transfers
  • American AirlinesAA2216 · AA2988
    6:37 AM7h07
    Portland International Airport
    3:44 PMO'Hare International Airport
    $3521One-way
    1 transfer

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

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FAQs: Travel from Portland, OR to Chicago, IL

Travel to Chicago, IL 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, IL.

FAQs
There are 3 options to travel between Portland, OR and Chicago, IL including taking a train, bus, and flight.
The cheapest way to travel from Portland, OR to Chicago, IL is a bus with an average price of $321 (€260).

This is compared to other travel options from Portland, OR to Chicago, IL:

A bus is $44 (€36) less than a flight for this route with tickets for a flight from Portland, OR to Chicago, IL costing on average $365 (€296).

A bus is $82 (€67) less than a train for this route with tickets for a train from Portland, OR to Chicago, IL costing on average $403 (€326).

The fastest way to travel from Portland, OR to Chicago, IL is by flight with an average journey time of 4h 17m.

Other travel options to Chicago, IL take longer:

Train takes on average 47h 35m.

Bus takes on average 72h 50m.

The distance from Portland, OR to Chicago, IL is approximately 1754 miles (2823 km).
The average frequency per day from Portland, OR to Chicago, IL is:
  • Around 46 flights per day.
  • Around 7 trains per day.
  • Around 4 buses per day.

However, we recommend checking specific travel dates for your route between Portland, OR and Chicago, IL as scheduled services by train, bus, and flight can vary by season or day of the week.

These are the most popular departure and arrival points from Portland, OR to Chicago, IL:
  • Flights mostly depart from Portland International Airport and arrive in O'Hare International Airport.
  • Trains mostly depart from Portland Union Station, Portland, OR and arrive in Chicago Union Station, Chicago, IL.
  • Buses mostly depart from Portland, NW Station Way (Station Place Parking Garage), OR and arrive in Chicago, Union Station (Amtrak), IL.
If finding a good deal is your main consideration for your trip from Portland, OR to Chicago, IL, then we'll help you find the best value travel companies for you:
  • Travel with Greyhound to go to Chicago, IL by bus.
  • Travel with American Airlines, Spirit Airlines, Alaska Airlines to go to Chicago, IL by flight.
  • Travel with Amtrak to go to Chicago, IL by train.
Yes, there are direct services available from Portland, OR to Chicago, IL with the following travel companies:
  • 5 direct flights per day with American Airlines, Alaska Airlines.
  • 1 direct trains per day with Amtrak.
Omio customers who travel from Portland, OR to Chicago, IL often also extend their vacation to go to San Francisco, CA, New York, NY, Indianapolis, IN, Milwaukee, WI, Minneapolis, MN. Omio can help you plan your trip by finding the best connections between Chicago, IL and these popular destinations at a great price.
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