There are 9 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 22 min

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

$175 - $557

Cheapest option

Fly Chicago O'Hare to Portland  •  6 h 34 min

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

$105 - $438

7 alternative options

Fly Chicago O'Hare to Eugene  •  8 h 5 min

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

$197 - $460

Fly Chicago O'Hare to Redmond  •  9 h 36 min

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

$225 - $969

Train to Milwaukee, fly to Portland  •  8 h 21 min

  1. Take the train from Chicago Union Station Amtrak to Milwaukee Intermodal Station Amtrak
  2. Fly from Milwaukee (MKE) to Portland (PDX) MKE - PDX

$193 - $427

Fly Chicago Midway to Medford  •  9 h 12 min

  1. Fly from Chicago Midway (MDW) to Medford (MFR) MDW - MFR

$264 - $1,206

Train  •  45 h 55 min

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

$270 - $850

Bus  •  47 h 51 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

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 once daily. Tickets cost $270 - $850 and the journey takes 45 h 55 min.

Airlines
Delta
Website
delta.com
Flights from Chicago Midway to Portland via Minneapolis
Ave. Duration
6 h 9 min
When
Every day
Estimated price
$240 - $850
Flights from Chicago Midway to Portland via Detroit
Ave. Duration
6 h 58 min
When
Monday, Thursday and Friday
Estimated price
$240 - $850
Flights from Chicago O'Hare to Portland via Minneapolis
Ave. Duration
6 h 4 min
When
Every day
Estimated price
$220 - $1,100
Flights from Chicago O'Hare to Portland via Salt Lake City
Ave. Duration
6 h 16 min
When
Monday, Saturday and Sunday
Estimated price
$220 - $1,100
Flights from Chicago O'Hare to Eugene via Salt Lake City
Ave. Duration
6 h 30 min
When
Monday to Saturday
Estimated price
$230 - $550
Flights from Chicago O'Hare to Eugene via Seattle
Ave. Duration
7 h 46 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$230 - $550
Flights from Chicago O'Hare to Redmond via Salt Lake City
Ave. Duration
6 h 9 min
When
Monday to Saturday
Estimated price
$210 - $900
Flights from Chicago O'Hare to Redmond via Seattle
Ave. Duration
6 h 31 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$220 - $950
Flights from Milwaukee to Portland via Minneapolis
Ave. Duration
6 h 7 min
When
Every day
Estimated price
$250 - $750
Flights from Milwaukee to Portland via Salt Lake City
Ave. Duration
6 h 38 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$250 - $750
Flights from Chicago Midway to Medford via Minneapolis, Salt Lake City
Ave. Duration
10 h 16 min
When
Every day
Estimated price
$260 - $1,200
Flights from Chicago Midway to Medford via Detroit, Salt Lake City
Ave. Duration
10 h 44 min
When
Every day
Estimated price
$290 - $1,200
Flights from Chicago Midway to Medford via Kansas City, Salt Lake City
Ave. Duration
7 h 39 min
When
Monday to Friday
Estimated price
$260 - $1,200
Flights from Chicago Midway to Medford via Denver, Salt Lake City
Ave. Duration
7 h 48 min
When
Saturday
Estimated price
$320 - $1,200
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 20 min
When
Every day
Estimated price
$240 - $950
Flights from Chicago O'Hare to Eugene via Denver
Ave. Duration
6 h 45 min
When
Every day
Estimated price
$210 - $650
Flights from Chicago O'Hare to Eugene via San Francisco
Ave. Duration
8 h 18 min
When
Every day
Estimated price
$210 - $650
Flights from Chicago O'Hare to Redmond via Denver
Ave. Duration
6 h 52 min
When
Every day
Estimated price
$220 - $950
Flights from Chicago O'Hare to Redmond via San Francisco
Ave. Duration
7 h 54 min
When
Every day
Estimated price
$250 - $1,100
Flights from Chicago O'Hare to Redmond via Los Angeles
Ave. Duration
8 h 10 min
When
Every day
Estimated price
$260 - $1,100
Flights from Milwaukee to Portland via Chicago O'Hare
Ave. Duration
6 h 19 min
When
Every day
Estimated price
$280 - $950
Flights from Milwaukee to Portland via Denver
Ave. Duration
6 h 33 min
When
Every day
Estimated price
$280 - $950
Flights from Chicago Midway to Medford via Denver
Ave. Duration
6 h 39 min
When
Saturday and Sunday
Estimated price
$280 - $1,200
Flights from Chicago Midway to Medford via San Francisco
Ave. Duration
7 h 2 min
When
Saturday and Sunday
Estimated price
$350 - $1,300
Flights from Chicago Midway to Medford via Los Angeles
Ave. Duration
7 h 35 min
When
Saturday and Sunday
Estimated price
$370 - $1,300
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to Portland
Ave. Duration
4 h 18 min
When
Every day
Estimated price
$280 - $900
Flights from Chicago Midway to Portland via Denver
Ave. Duration
6 h 13 min
When
Monday to Saturday
Estimated price
$280 - $900
Flights from Chicago Midway to Portland via St. Louis
Ave. Duration
6 h 15 min
When
Sunday
Estimated price
$280 - $900
Flights from Chicago Midway to Portland via Kansas City
Ave. Duration
6 h 35 min
When
Saturday
Estimated price
$280 - $900
Flights from Milwaukee to Portland via Denver
Ave. Duration
6 h 11 min
When
Every day
Estimated price
$270 - $800
Flights from Milwaukee to Portland via St. Louis
Ave. Duration
6 h 25 min
When
Saturday and Sunday
Estimated price
$270 - $800
Alaska Airlines, Inc.
Website
alaskaair.com
Flights from Chicago O'Hare to Portland
Ave. Duration
4 h 21 min
When
Every day
Estimated price
$210 - $800
Flights from Chicago O'Hare to Portland via Seattle
Ave. Duration
6 h 9 min
When
Every day
Estimated price
$210 - $800
Flights from Chicago O'Hare to Eugene via Seattle
Ave. Duration
7 h 22 min
When
Every day
Estimated price
$150 - $470
Flights from Chicago O'Hare to Eugene via Portland
Ave. Duration
8 h 9 min
When
Every day
Estimated price
$150 - $470
Flights from Chicago O'Hare to Redmond via Portland
Ave. Duration
6 h 40 min
When
Every day
Estimated price
$220 - $950
Flights from Chicago O'Hare to Redmond via Seattle
Ave. Duration
8 h 33 min
When
Every day
Estimated price
$230 - $950
Flights from Milwaukee to Portland
Ave. Duration
4 h 35 min
When
Every day
Estimated price
$220 - $850
Flights from Chicago Midway to Medford via Seattle
Ave. Duration
7 h 47 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$340 - $1,200
Flights from Chicago Midway to Medford via Portland
Ave. Duration
7 h 2 min
When
Saturday
Estimated price
$330 - $1,200
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Portland
Ave. Duration
4 h 15 min
When
Every day
Estimated price
$210 - $950
Flights from Chicago O'Hare to Eugene via Phoenix
Ave. Duration
8 h 24 min
When
Every day
Estimated price
$220 - $600
Flights from Chicago O'Hare to Eugene via Los Angeles
Ave. Duration
9 h 20 min
When
Every day
Estimated price
$220 - $600
Flights from Chicago O'Hare to Eugene via Portland
Ave. Duration
7 h 39 min
When
Every day
Estimated price
$220 - $600
Flights from Chicago O'Hare to Redmond via Phoenix
Ave. Duration
7 h 46 min
When
Every day
Estimated price
$260 - $950
Flights from Chicago Midway to Medford via Portland
Ave. Duration
7 h 2 min
When
Saturday
Estimated price
$330 - $1,200
Flights from Chicago Midway to Medford via Phoenix
Ave. Duration
7 h 5 min
When
Saturday
Estimated price
$360 - $1,300
Spirit Airlines
Website
spirit.com
Flights from Chicago O'Hare to Portland
Ave. Duration
4 h 20 min
When
Every day
Estimated price
$160 - $700
Allegiant Air
Website
allegiantair.com
Flights from Chicago Midway to Medford via Las Vegas
Ave. Duration
8 h 6 min
When
Thursday
Estimated price
$340 - $1,200
Train operators
Amtrak
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Chicago Union Station Amtrak to Milwaukee Intermodal Station Amtrak
Ave. Duration
1 h 29 min
Frequency
Hourly
Estimated price
$28 - $60
Website
amtrak.com
Coach Seat
$28 - $45
Flexi Coach Seat
$50 - $75
Business Coach Seat
$40 - $60
Room
$150 - $210
Train from Chicago Union Station Amtrak to Portland Union Station Amtrak
Ave. Duration
45 h 55 min
Frequency
Once 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
Phone
+1 214-849-8100
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
Schedules at
jeffersonlines.com

Want to know more about travelling around United States

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Questions & Answers

The distance between Chicago and Oregon is 2688 km. The road distance is 3413 km.

The cheapest way to get from Chicago to Oregon is to fly which costs $100 - $440 and takes 6 h 34 min.

The quickest way to get from Chicago to Oregon is to fly which takes 6 h 22 min and costs $170 - $600.

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

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 51 min.

It takes approximately 6 h 22 min to get from Chicago to Oregon, including transfers.