There are 8 ways to get from Chicago to Oregon 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 Chicago Midway to Portland  •  6 h 23 min

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

$175 - $557

Cheapest option

Fly Chicago O'Hare to Portland  •  6 h 36 min

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

$105 - $438

6 alternative options

Fly Chicago O'Hare to Eugene  •  8 h 17 min

  1. Fly from Chicago O'Hare (ORD) to Eugene (EUG) ORD - EUG

$197 - $460

Fly Chicago O'Hare to Medford  •  9 h 38 min

  1. Fly from Chicago O'Hare (ORD) to Medford (MFR) ORD - MFR

$224 - $957

Fly Chicago O'Hare to Redmond  •  10 h 6 min

  1. Fly from Chicago O'Hare (ORD) to Redmond (RDM) ORD - RDM

$225 - $964

Train  •  45 h 55 min

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

$270 - $850

Bus  •  47 h 52 min

  1. Take the bus from Chicago, Il to Minneapolis, Mn
  2. Take the bus from Minneapolis, MN to Missoula, MT 933
  3. Take the bus from Missoula, Mt to Spokane, Wa
  4. Take the bus from Spokane, Wa to Portland, Or

$318 - $572

Drive  •  33 h 3 min

  1. Drive from Chicago to Portland 2133.1 miles

$200 - $310

Questions & Answers

The cheapest way to get from Chicago to Oregon is to fly which costs $100 - $440 and takes 6 h 36 min.

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The quickest way to get from Chicago to Oregon is to fly which costs $170 - $600 and takes 6 h 23 min.

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No, there is no direct bus from Chicago to Oregon. However, there are services departing from Chicago, Il and arriving at Portland, Or via Hennepin Ave & Maple St, Minneapolis, MN, Missoula, Mt and Spokane, Wa. The journey, including transfers, takes approximately 47 h 52 min.

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Yes, there is a direct train departing from Chicago Union Station station and arriving at Portland Union Station station. Services depart twice daily, and operate every day. The journey takes approximately 45 h 55 min.

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The distance between Chicago and Oregon is 1680 miles. The road distance is 2133.1 miles.

Get driving directions

The best way to get from Chicago to Oregon without a car is to train which takes 45 h 55 min and costs $270 - $850.

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It takes approximately 6 h 23 min to get from Chicago to Oregon, including transfers.

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Chicago to Oregon bus services, operated by Greyhound USA, depart from Chicago, Il station.

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

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The best way to get from Chicago to Oregon is to fly which takes 6 h 23 min and costs $170 - $600. Alternatively, you can train, which costs $270 - $850 and takes 45 h 55 min, you could also bus, which costs $310 - $600 and takes 47 h 52 min.

Mode details

Map of how to get from Chicago to Oregon.
Launch map view
  • Distance: 1679.8 miles
  • Duration: 6 h 23 min

What companies run services between Chicago, IL, USA and Oregon, USA?

Southwest Airlines and Delta fly from Chicago to Portland hourly. Alternatively, Amtrak operates a train from Chicago to Portland twice daily. Tickets cost $270 - $850 and the journey takes 45 h 55 min.

Airlines
United Airlines
Website
united.com
Flights from Chicago O'Hare to Portland
Ave. Duration
4 h 24 min
When
Every day
Estimated price
$240 - $950
Flights from Chicago O'Hare to Portland via Denver
Ave. Duration
6 h 5 min
When
Monday, Thursday, Friday and Sunday
Estimated price
$240 - $950
Flights from Chicago O'Hare to Eugene via Denver
Ave. Duration
7 h 18 min
When
Every day
Estimated price
$210 - $650
Flights from Chicago O'Hare to Eugene via San Francisco
Ave. Duration
8 h 14 min
When
Every day
Estimated price
$210 - $650
Flights from Chicago O'Hare to Medford via Denver
Ave. Duration
7 h 13 min
When
Every day
Estimated price
$240 - $1,000
Flights from Chicago O'Hare to Medford via San Francisco
Ave. Duration
7 h 45 min
When
Every day
Estimated price
$260 - $1,100
Flights from Chicago O'Hare to Medford via Los Angeles
Ave. Duration
8 h 48 min
When
Every day
Estimated price
$270 - $1,100
Flights from Chicago O'Hare to Medford via Madison, Denver
Ave. Duration
8 h 32 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$240 - $1,000
Flights from Chicago O'Hare to Medford via St. Louis, Denver
Ave. Duration
8 h 45 min
When
Every day
Estimated price
$250 - $1,100
Flights from Chicago O'Hare to Redmond via Denver
Ave. Duration
7 h 8 min
When
Every day
Estimated price
$220 - $950
Flights from Chicago O'Hare to Redmond via San Francisco
Ave. Duration
7 h 59 min
When
Every day
Estimated price
$250 - $1,100
Flights from Chicago O'Hare to Redmond via Los Angeles
Ave. Duration
8 h 21 min
When
Every day
Estimated price
$260 - $1,100
Flights from Chicago O'Hare to Redmond via Madison, Denver
Ave. Duration
8 h 5 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$230 - $950
Flights from Chicago O'Hare to Redmond via Grand Rapids, Denver
Ave. Duration
8 h 22 min
When
Every day
Estimated price
$240 - $1,000
Alaska Airlines, Inc.
Website
alaskaair.com
Flights from Chicago O'Hare to Portland
Ave. Duration
4 h 27 min
When
Every day
Estimated price
$210 - $800
Flights from Chicago O'Hare to Portland via Seattle
Ave. Duration
6 h 11 min
When
Every day
Estimated price
$210 - $800
Flights from Chicago O'Hare to Eugene via Portland
Ave. Duration
8 h 13 min
When
Every day
Estimated price
$150 - $470
Flights from Chicago O'Hare to Eugene via Seattle
Ave. Duration
8 h 6 min
When
Every day
Estimated price
$150 - $470
Flights from Chicago O'Hare to Medford via Seattle
Ave. Duration
7 h 2 min
When
Every day
Estimated price
$250 - $1,100
Flights from Chicago O'Hare to Medford via Portland
Ave. Duration
7 h 17 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$240 - $1,000
Flights from Chicago O'Hare to Redmond via Seattle
Ave. Duration
7 h 56 min
When
Every day
Estimated price
$230 - $950
Flights from Chicago O'Hare to Redmond via Portland
Ave. Duration
8 h 52 min
When
Every day
Estimated price
$220 - $950
Delta
Website
delta.com
Flights from Chicago Midway to Portland via Minneapolis
Ave. Duration
6 h 35 min
When
Every day
Estimated price
$240 - $850
Flights from Chicago O'Hare to Portland via Minneapolis
Ave. Duration
6 h 8 min
When
Every day
Estimated price
$220 - $1,100
Flights from Chicago O'Hare to Portland via Salt Lake City
Ave. Duration
6 h 13 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$220 - $1,100
Flights from Chicago O'Hare to Eugene via Salt Lake City
Ave. Duration
7 h 57 min
When
Every day
Estimated price
$230 - $550
Flights from Chicago O'Hare to Eugene via Seattle
Ave. Duration
6 h 42 min
When
Monday to Friday
Estimated price
$230 - $550
Flights from Chicago O'Hare to Medford via Salt Lake City
Ave. Duration
9 h 33 min
When
Every day
Estimated price
$220 - $950
Flights from Chicago O'Hare to Medford via Seattle
Ave. Duration
9 h 47 min
When
Every day
Estimated price
$230 - $1,000
Flights from Chicago O'Hare to Redmond via Seattle
Ave. Duration
7 h 55 min
When
Every day
Estimated price
$220 - $950
Flights from Chicago O'Hare to Redmond via Salt Lake City
Ave. Duration
8 h 25 min
When
Every day
Estimated price
$210 - $900
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to Portland
Ave. Duration
4 h 17 min
When
Every day
Estimated price
$280 - $900
Flights from Chicago Midway to Portland via St. Louis
Ave. Duration
6 h 5 min
When
Monday to Friday
Estimated price
$280 - $900
Flights from Chicago Midway to Portland via Denver
Ave. Duration
6 h 27 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$280 - $900
Flights from Chicago Midway to Portland via Kansas City
Ave. Duration
6 h 45 min
When
Saturday
Estimated price
$280 - $900
Flights from Chicago Midway to Portland via Phoenix
Ave. Duration
7 h 10 min
When
Saturday
Estimated price
$280 - $900
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Portland
Ave. Duration
4 h 16 min
When
Every day
Estimated price
$210 - $950
Flights from Chicago O'Hare to Eugene via Phoenix
Ave. Duration
8 h 15 min
When
Every day
Estimated price
$220 - $600
Flights from Chicago O'Hare to Eugene via Los Angeles
Ave. Duration
9 h 18 min
When
Every day
Estimated price
$220 - $600
Flights from Chicago O'Hare to Medford via Phoenix
Ave. Duration
7 h 8 min
When
Every day
Estimated price
$270 - $1,000
Flights from Chicago O'Hare to Redmond via Phoenix
Ave. Duration
7 h 57 min
When
Every day
Estimated price
$260 - $950
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 Chicago Union Station to Portland Union Station
Ave. Duration
45 h 55 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 Chicago, Il to Minneapolis, Mn
Ave. Duration
8 h 9 min
Frequency
Hourly
Estimated price
$40 - $110
Website
greyhound.com
Economy
$40 - $70
Flexible
$80 - $110
Bus from Missoula, Mt to Spokane, Wa
Ave. Duration
4 h 20 min
Frequency
Every 3 hours
Estimated price
$26 - $65
Website
greyhound.com
Economy
$26 - $40
Flexible
$45 - $65
Bus from Spokane, Wa to Portland, Or
Ave. Duration
6 h 30 min
Frequency
Every 2 hours
Estimated price
$35 - $95
Website
greyhound.com
Economy
$35 - $60
Flexible
$70 - $95
Jefferson Lines
Phone
800-451-5333
Email
info@jeffersonlines.com
Website
jeffersonlines.com
Bus from Minneapolis, MN to Missoula, MT
Ave. Duration
25 h 45 min
Frequency
Every 3 hours
Estimated price
$210 - $300
Book at
jeffersonlines.com

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More Questions & Answers

The quickest flight from Chicago Midway Airport to Portland Airport is the direct flight which takes 4 h 15 min.

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Chicago to Oregon bus services, operated by Greyhound USA, arrive at Portland, Or station.

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Oregon is 2 h behind Chicago. It is currently 12:34 PM in Chicago and 10:34 AM in Oregon.

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

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Yes, the driving distance between Chicago to Oregon is 2133 miles. It takes approximately 33 h 3 min to drive from Chicago to Oregon.

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Delta and Southwest Airlines offer flights from Chicago Midway Airport to Portland Airport.

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Book your Chicago to Oregon train tickets online with Rome2rio.

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The best way to get from Chicago to Chicago Midway Airport is to subway which takes 23 min and costs $2 - $4.

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