There are 6 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 15 min

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

$104 - $438

5 alternative options

Fly to Chicago Midway  •  6 h 9 min

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

$174 - $556

Fly to Milwaukee, train  •  8 h 33 min

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

$192 - $428

Train  •  45 h 10 min

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

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

United Airlines, Alaska Airlines, Inc. and four other airlines fly from Portland to Chicago hourly. Alternatively, Amtrak operates a train from Portland to Chicago once 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
4 h 1 min
When
Every day
Estimated price
$280 - $900
Flights from Portland to Chicago Midway via Kansas City
Ave. Duration
5 h 53 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$280 - $900
Flights from Portland to Chicago Midway via St. Louis
Ave. Duration
6 h 2 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$280 - $900
Flights from Portland to Chicago Midway via Denver
Ave. Duration
6 h 6 min
When
Monday to Saturday
Estimated price
$280 - $900
Flights from Portland to Milwaukee via Denver
Ave. Duration
5 h 47 min
When
Every day
Estimated price
$270 - $800
Flights from Portland to Milwaukee via St. Louis
Ave. Duration
5 h 57 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$270 - $800
Delta
Website
delta.com
Flights from Portland to Chicago O'Hare via Minneapolis
Ave. Duration
5 h 47 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 46 min
When
Every day
Estimated price
$220 - $1,100
Flights from Portland to Chicago Midway via Minneapolis
Ave. Duration
6 h
When
Every day
Estimated price
$240 - $850
Flights from Portland to Milwaukee via Minneapolis
Ave. Duration
5 h 29 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$250 - $750
Flights from Portland to Milwaukee via Salt Lake City
Ave. Duration
5 h 52 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$250 - $750
United Airlines
Website
united.com
Flights from Portland to Chicago O'Hare
Ave. Duration
3 h 57 min
When
Every day
Estimated price
$240 - $950
Flights from Portland to Chicago O'Hare via Denver
Ave. Duration
5 h 52 min
When
Every day
Estimated price
$240 - $950
Flights from Portland to Milwaukee via Chicago O'Hare
Ave. Duration
5 h 52 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$280 - $950
Flights from Portland to Milwaukee via Denver
Ave. Duration
6 h 2 min
When
Every day
Estimated price
$280 - $950
Alaska Airlines, Inc.
Website
alaskaair.com
Flights from Portland to Chicago O'Hare
Ave. Duration
4 h 5 min
When
Every day
Estimated price
$210 - $800
Flights from Portland to Chicago O'Hare via Seattle
Ave. Duration
5 h 58 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$210 - $800
Flights from Portland to Milwaukee
Ave. Duration
3 h 47 min
When
Every day
Estimated price
$220 - $850
Flights from Portland to Milwaukee via Seattle
Ave. Duration
5 h 45 min
When
Tuesday, Wednesday and Saturday
Estimated price
$220 - $850
American Airlines
Website
aa.com
Flights from Portland to Chicago O'Hare
Ave. Duration
4 h 11 min
When
Every day
Estimated price
$210 - $950
Spirit Airlines
Website
spirit.com
Flights from Portland to Chicago O'Hare
Ave. Duration
4 h 6 min
When
Every day
Estimated price
$160 - $700
Train operators
Amtrak
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Milwaukee Intermodal Station Amtrak to Chicago Union Station Amtrak
Ave. Duration
1 h 29 min
Frequency
Every 4 hours
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 Portland Union Station Amtrak to Chicago Union Station Amtrak
Ave. Duration
45 h 10 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 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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Questions & Answers

The distance between Portland and Chicago is 2824 km. The road distance is 3414 km.

The cheapest way to get from Portland to Chicago is to fly which costs $100 - $440 and takes 6 h 15 min.

The quickest way to get from Portland to Chicago is to fly which takes 6 h 9 min and costs $170 - $600.

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

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.

It takes approximately 6 h 15 min to get from Portland to Chicago, including transfers.