There are 5 ways to get from Portland to Chicago by plane, train, bus or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner.

Recommended option

Fly to Chicago O'Hare  •  6 h 1 min

  1. Fly from Portland (PDX) to Chicago O'Hare (ORD) PDX - ORD

$104 - $438

4 alternative options

Fly to Chicago Midway  •  6 h 5 min

  1. Fly from Portland (PDX) to Chicago Midway (MDW) PDX - MDW

$174 - $556

Train  •  45 h 10 min

  1. Take the train from Portland Union Station to Chicago Union Station Empire Builder

$270 - $850

Bus  •  2 days 4 h

  1. Take the bus from Portland, Or to Denver, Co
  2. Take the bus from Denver, CO to Des Moines, IA
  3. Take the bus from Des Moines, IA to Chicago, IL

$262 - $526

Drive  •  33 h 3 min

  1. Drive from Portland to Chicago 2134 miles

$200 - $310

Questions & Answers

The cheapest way to get from Portland to Chicago is to fly which costs $100 - $440 and takes 6 h 1 min.

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The quickest way to get from Portland to Chicago is to fly which costs $100 - $440 and takes 6 h 1 min.

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No, there is no direct bus from Portland to Chicago. However, there are services departing from Portland, Or and arriving at Chicago, IL via Denver, CO and Des Moines, IA. The journey, including transfers, takes approximately 2 days 4 h.

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Yes, there is a direct train departing from Portland Union Station station and arriving at Chicago Union Station station. Services depart twice daily, and operate every day. The journey takes approximately 45 h 10 min.

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The distance between Portland and Chicago is 1765 miles. The road distance is 2134 miles.

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The best way to get from Portland to Chicago without a car is to train which takes 45 h 10 min and costs $270 - $850.

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It takes approximately 6 h 1 min to get from Portland to Chicago, including transfers.

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Portland to Chicago bus services, operated by Greyhound USA, depart from Portland, Or station.

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Portland to Chicago train services, operated by Amtrak, arrive at Portland Union Station.

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The best way to get from Portland to Chicago is to fly which takes 6 h 1 min and costs $100 - $440. Alternatively, you can train, which costs $270 - $850 and takes 45 h 10 min, you could also bus, which costs $260 - $550 and takes 2 days 4 h.

Mode details

Map of how to get from Portland to Chicago.
Launch map view
  • Distance: 1764.8 miles
  • Duration: 6 h 1 min

What companies run services between Portland, OR, USA and Chicago, IL, USA?

United Airlines, Alaska Airlines, Inc. and three other airlines fly from Portland to Chicago hourly. Alternatively, Amtrak operates a train from Portland to Chicago twice daily. Tickets cost $270 - $850 and the journey takes 45 h 10 min.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Portland to Chicago Midway
Ave. Duration
3 h 58 min
When
Every day
Estimated price
$280 - $900
Flights from Portland to Chicago Midway via St. Louis
Ave. Duration
5 h 46 min
When
Every day
Estimated price
$280 - $900
Flights from Portland to Chicago Midway via Kansas City
Ave. Duration
5 h 55 min
When
Monday to Friday
Estimated price
$280 - $900
Flights from Portland to Chicago Midway via Denver
Ave. Duration
6 h 11 min
When
Monday to Saturday
Estimated price
$280 - $900
Flights from Portland to Chicago Midway via Las Vegas
Ave. Duration
6 h 20 min
When
Saturday
Estimated price
$280 - $900
Delta
Website
delta.com
Flights from Portland to Chicago O'Hare via Minneapolis
Ave. Duration
5 h 51 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$220 - $1,100
Flights from Portland to Chicago O'Hare via Salt Lake City
Ave. Duration
5 h 52 min
When
Every day
Estimated price
$220 - $1,100
Flights from Portland to Chicago O'Hare via Seattle
Ave. Duration
5 h 58 min
When
Monday to Friday
Estimated price
$220 - $1,100
Flights from Portland to Chicago Midway via Minneapolis
Ave. Duration
6 h 17 min
When
Monday to Friday
Estimated price
$240 - $850
United Airlines
Website
united.com
Flights from Portland to Chicago O'Hare
Ave. Duration
3 h 52 min
When
Every day
Estimated price
$240 - $950
American Airlines
Website
aa.com
Flights from Portland to Chicago O'Hare
Ave. Duration
4 h 5 min
When
Every day
Estimated price
$210 - $950
Alaska Airlines, Inc.
Website
alaskaair.com
Flights from Portland to Chicago O'Hare
Ave. Duration
3 h 54 min
When
Every day
Estimated price
$210 - $800
Train operators
Amtrak

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Portland Union Station to Chicago Union Station
Ave. Duration
45 h 10 min
Frequency
Twice daily
Estimated price
$270 - $850
Website
amtrak.com
Coach Seat
$270 - $410
Flexi Coach Seat
$490 - $700
Business Coach Seat
$550 - $850
Room
$1,000 - $1,500
Bus operators
Greyhound USA

Greyhound is a leading bus company based in Dallas, Texas, serving over 3800 destinations across North America, Mexico and Canada. Greyhound carries around 18 million passengers a year who travel 5.4 billion miles (8.6 billion km) a year on their fleet of around 1700 vehicles. For travel flexibility, you can board or get off a Greyhound bus at official Greyhound stations, partner stations and curbside stops. There are around 230 Greyhound stations across the US where you can both catch your bus and buy tickets, that are also available on the official website and via the mobile app.

Rome2rio's guide to Greyhound USA
Contact Details
Phone
+1 214-849-8100/1-800-231-2222
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from Portland, Or to Denver, Co
Ave. Duration
28 h 55 min
Frequency
Hourly
Estimated price
$120 - $320
Website
greyhound.com
Economy
$120 - $210
Flexible
$240 - $320
Burlington Trailways
Website
burlingtontrailways.com
Bus from Denver, CO to Des Moines, IA
Ave. Duration
14 h 15 min
Frequency
Once daily
Estimated price
$90 - $130
Schedules at
burlingtontrailways.com
Book at
burlingtontrailways.com
Bus from Des Moines, IA to Chicago, IL
Ave. Duration
6 h 50 min
Frequency
Every 3 hours
Estimated price
$45 - $80
Schedules at
burlingtontrailways.com
Book at
burlingtontrailways.com

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More Questions & Answers

The quickest flight from Portland Airport to Chicago O'Hare Airport is the direct flight which takes 3 h 38 min.

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Portland to Chicago bus services, operated by Burlington Trailways, arrive at Chicago, IL station.

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Chicago is 2 h ahead of Portland. It is currently 8:24 AM in Portland and 10:24 AM in Chicago.

Portland to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.

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Yes, the driving distance between Portland to Chicago is 2134 miles. It takes approximately 33 h 3 min to drive from Portland to Chicago.

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Alaska Airlines, Inc., American Airlines, United Airlines and Delta offer flights from Portland Airport to Chicago O'Hare Airport.

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Book your Portland to Chicago train tickets online with Rome2rio.

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There are 574+ hotels available in Chicago. Prices start at $104 USD per night.

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The best way to get from Portland to Portland Airport is to tram which takes 35 min and costs $3.

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