Bus Portland, OR to Chicago: Compare prices and save money

Compare all timetables for the bus from Portland, OR to Chicago

Here is a selection of the cheapest bus trips from the schedule from Portland, OR to Chicago from various bus operators like Greyhound US or FlixBus for the next days.

today

tomorrow

$301

Tuesday

Wednesday

Thursday

$329

Friday

$231

Saturday

Cheapest bus trips tomorrow
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	60h 20m	2:00 AM	Portland, OR	Union Bus Station	4:20 PM	Chicago	Downtown Bus Station	Economy	$301	A Bus from Greyhound US goes from Union Bus Station, Portland, OR (USA) at 12/15/2025 2:00:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/17/2025 4:20:00 PM. 50 Economy ticket for $301 per person are available. Travel duration is 60h 20m
FlixBus	78h 10m	8:00 PM	Portland, OR	Union Bus Station	4:10 AM	Chicago	Downtown Bus Station	Economy	$311	A Bus from FlixBus goes from Union Bus Station, Portland, OR (USA) at 12/15/2025 8:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/19/2025 4:10:00 AM. 50 Economy ticket for $311 per person are available. Travel duration is 78h 10m
Greyhound US	76h 0m	2:00 AM	Portland, OR	Union Bus Station	8:00 AM	Chicago	Union Station	Economy	$320	A Bus from Greyhound US goes from Union Bus Station, Portland, OR (USA) at 12/15/2025 2:00:00 AM to Union Station, Chicago (USA) arriving at 12/18/2025 8:00:00 AM. 50 Economy ticket for $320 per person are available. Travel duration is 76h 0m
FlixBus	82h 0m	8:00 PM	Portland, OR	Union Bus Station	8:00 AM	Chicago	Union Station	Economy	$324	A Bus from FlixBus goes from Union Bus Station, Portland, OR (USA) at 12/15/2025 8:00:00 PM to Union Station, Chicago (USA) arriving at 12/19/2025 8:00:00 AM. 50 Economy ticket for $324 per person are available. Travel duration is 82h 0m

Did you know that if you travel from Portland, OR to Chicago via Davenport, IA, you can save more than $46? You can find the corresponding connections below.
- FlixBus
  
  78h 55m
  
  0
  
  2:00 AM
  
  Portland, OR
  Union Bus Station
  
  1:05 PM
  
  Davenport, IA
  Ground Transporation Center
  
  0
  
  Economy
  
  $224
  
  A Bus from FlixBus goes from Union Bus Station, Portland, OR (USA) at 12/15/2025 2:00:00 AM to Ground Transporation Center, Davenport, IA (USA) arriving at 12/17/2025 1:05:00 PM. 50 Economy ticket for $224 per person are available. Travel duration is 57h 5m
- Busbud
  
  4h 25m
  
  0
  
  6:30 AM
  
  Davenport, IA
  Ground Transporation Center
  
  10:55 AM
  
  Chicago
  Downtown Bus Station
  
  0
  
  Economy
  
  $31
  
  A Bus from Busbud goes from Ground Transporation Center, Davenport, IA (USA) at 12/18/2025 6:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/18/2025 10:55:00 AM. 50 Economy ticket for $31 per person are available. Travel duration is 4h 25m
Travel time is 16h 35m longer, but you will save $46

Cheapest bus trips Thursday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	60h 20m	2:00 AM	Portland, OR	Union Bus Station	4:20 PM	Chicago	Downtown Bus Station	Economy	$329	A Bus from Greyhound US goes from Union Bus Station, Portland, OR (USA) at 12/18/2025 2:00:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/20/2025 4:20:00 PM. 50 Economy ticket for $329 per person are available. Travel duration is 60h 20m
FlixBus	78h 10m	8:00 PM	Portland, OR	Union Bus Station	4:10 AM	Chicago	Downtown Bus Station	Economy	$416	A Bus from FlixBus goes from Union Bus Station, Portland, OR (USA) at 12/18/2025 8:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/22/2025 4:10:00 AM. 50 Economy ticket for $416 per person are available. Travel duration is 78h 10m
Greyhound US	76h 0m	2:00 AM	Portland, OR	Union Bus Station	8:00 AM	Chicago	Union Station	Economy	$417	A Bus from Greyhound US goes from Union Bus Station, Portland, OR (USA) at 12/18/2025 2:00:00 AM to Union Station, Chicago (USA) arriving at 12/21/2025 8:00:00 AM. 50 Economy ticket for $417 per person are available. Travel duration is 76h 0m
FlixBus	82h 0m	8:00 PM	Portland, OR	Union Bus Station	8:00 AM	Chicago	Union Station	Economy	$417	A Bus from FlixBus goes from Union Bus Station, Portland, OR (USA) at 12/18/2025 8:00:00 PM to Union Station, Chicago (USA) arriving at 12/22/2025 8:00:00 AM. 50 Economy ticket for $417 per person are available. Travel duration is 82h 0m

Did you know that if you travel from Portland, OR to Chicago via Davenport, IA, you can save more than $74? You can find the corresponding connections below.
- FlixBus
  
  78h 55m
  
  0
  
  2:00 AM
  
  Portland, OR
  Union Bus Station
  
  1:05 PM
  
  Davenport, IA
  Ground Transporation Center
  
  0
  
  Economy
  
  $224
  
  A Bus from FlixBus goes from Union Bus Station, Portland, OR (USA) at 12/15/2025 2:00:00 AM to Ground Transporation Center, Davenport, IA (USA) arriving at 12/17/2025 1:05:00 PM. 50 Economy ticket for $224 per person are available. Travel duration is 57h 5m
- Busbud
  
  4h 25m
  
  0
  
  6:30 AM
  
  Davenport, IA
  Ground Transporation Center
  
  10:55 AM
  
  Chicago
  Downtown Bus Station
  
  0
  
  Economy
  
  $31
  
  A Bus from Busbud goes from Ground Transporation Center, Davenport, IA (USA) at 12/18/2025 6:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/18/2025 10:55:00 AM. 50 Economy ticket for $31 per person are available. Travel duration is 4h 25m
Travel time is 16h 35m longer, but you will save $74

Cheapest bus trips Friday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	62h 35m	2:00 AM	Portland, OR	Union Bus Station	6:35 PM	Chicago	95th Red Line Station	Economy	$231	A Bus from Greyhound US goes from Union Bus Station, Portland, OR (USA) at 12/19/2025 2:00:00 AM to 95th Red Line Station, Chicago (USA) arriving at 12/21/2025 6:35:00 PM. 50 Economy ticket for $231 per person are available. Travel duration is 62h 35m
Greyhound US	60h 20m	2:00 AM	Portland, OR	Union Bus Station	4:20 PM	Chicago	Downtown Bus Station	Economy	$345	A Bus from Greyhound US goes from Union Bus Station, Portland, OR (USA) at 12/19/2025 2:00:00 AM to Downtown Bus Station, Chicago (USA) arriving at 12/21/2025 4:20:00 PM. 50 Economy ticket for $345 per person are available. Travel duration is 60h 20m
Greyhound US	76h 0m	2:00 AM	Portland, OR	Union Bus Station	8:00 AM	Chicago	Union Station	Economy	$418	A Bus from Greyhound US goes from Union Bus Station, Portland, OR (USA) at 12/19/2025 2:00:00 AM to Union Station, Chicago (USA) arriving at 12/22/2025 8:00:00 AM. 50 Economy ticket for $418 per person are available. Travel duration is 76h 0m
FlixBus	78h 10m	8:00 PM	Portland, OR	Union Bus Station	4:10 AM	Chicago	Downtown Bus Station	Economy	$445	A Bus from FlixBus goes from Union Bus Station, Portland, OR (USA) at 12/19/2025 8:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 12/23/2025 4:10:00 AM. 50 Economy ticket for $445 per person are available. Travel duration is 78h 10m
FlixBus	82h 0m	8:00 PM	Portland, OR	Union Bus Station	8:00 AM	Chicago	Union Station	Economy	$448	A Bus from FlixBus goes from Union Bus Station, Portland, OR (USA) at 12/19/2025 8:00:00 PM to Union Station, Chicago (USA) arriving at 12/23/2025 8:00:00 AM. 50 Economy ticket for $448 per person are available. Travel duration is 82h 0m

Best Price Offer: The price for the cheapest bus from Portland, OR to Chicago is $227 on 12/21/2025. Flexible travelers save on ticket prices.

Frequency of bus connections between Portland, OR and Chicago

See here how frequent the connections between Portland, OR and Chicago are, during different times and days of the week.

Friday is the busiest day, with more than 5 daily buses from Portland, OR to Chicago. Monday has instead the fewest connections, with only 4 daily coaches between Portland, OR and Chicago.

The busiest time of the day is the Night, with 7 buses from Portland, OR to Chicago, while Evening sees the fewest connections between Portland, OR and Chicago, with 6 offers.

Facts about the bus from Portland, OR to Chicago

Compare all providers like Greyhound US and FlixBus that travel 4 times every day by bus from Portland, OR to Chicago in one click! Book your bus ticket from Portland, OR to Chicago starting from $227!

Cheapest Bus	$227
Fastest Bus	62h 20m
Earliest Bus	2:00 AM
Latest Bus	8:00 PM
Daily Bus Routes	4 Ø
Distance	1,754.6 miles
Bus Companies	Greyhound US and FlixBus

Cheapest bus connections from Portland, OR to Chicago

Every day, 4 buses from 2 bus companies leave Portland, OR for Chicago: in the table below, you will find the cheapest prices for a bus ticket for this route, starting from 12/14/2025 and for the following days.

Sunday

Monday

Tuesday

Wednesday

Thursday

Friday

Saturday

Sunday 12/14

Monday 12/15

$301

Tuesday 12/16

Wednesday 12/17

Thursday 12/18

$329

Friday 12/19

$231

Saturday 12/20

Sunday 12/21

$227

Monday 12/22

Tuesday 12/23

$248

Wednesday 12/24

Thursday 12/25

Friday 12/26

Saturday 12/27

Sunday 12/28

Monday 12/29

Tuesday 12/30

Wednesday 12/31

Thursday 01/01

Friday 01/02

Saturday 01/03

Sunday 01/04

Monday 01/05

Tuesday 01/06

Wednesday 01/07

Thursday 01/08

Friday 01/09

Saturday 01/10

The cheapest time to travel from Portland, OR to Chicago

See here on which day and which time of the day you can find the cheapest bus ticket from Portland, OR to Chicago, for the next 30 days.

With a price starting from $231, Friday is the cheapest day for a bus from Portland, OR to Chicago. Thursday instead is the most expensive day with prices starting from $329.

Night is the cheapest day time for bus tickets from Portland, OR to Chicago, with $227. Evening is the most expensive time of the day with prices starting from $311.

How to save money travelling from Portland, OR to Chicago

Travel can be expensive, but it doesn't need to be! Do you want to avoid paying a terrible price for your trip? Then follow these quick steps to save money:

Book the ticket from Portland, OR to Chicago in advance! The earlier you book, the cheaper usually the price is. Also, you will be sure to have a place on the bus from Portland, OR to Chicago, compared instead if you buy it at the last moment, or directly at the station.

If you can, avoid travelling at peak times. Instead of weekend, try travelling during the week. Travelling in the evening or at night it’s also cheaper, and later buses from Portland, OR to Chicago are also emptier.

Beloved bus companies from Portland, OR to Chicago

These are the most booked bus companies between Portland, OR to Chicago from our users.

Greyhound US from Portland, OR to Chicago

Here you will find the key facts about the Greyhound US bus route Portland, OR to Chicago:

Cheapest Price	$231
Fastest Bus	62h 20m
Earliest Bus	2:00 AM
Last Bus	2:00 AM
Daily Connections	2 Ø
Found on	12/11/2025

All bus stations and stops in Portland, OR and Chicago

In the map below, you can see where to find all bus stations in Portland, OR and Chicago.

Union Bus Station

NW 6th Ave 800

Greyhound Bus Station

NW Station Way 1090

NW Station Way

NW Station Way 1090

Portland Bolt Lloyd Center

NE 13th Ave 1060

SE 102nd & Washington Bus Stop

95th Red Line Station

W. 95th St 14

Downtown Bus Station

West Harrison Street 630-670

Union Station

S Canal St 225

Cumberland CTA

N Cumberland Ave 5800

Canal & Van Buren

S Canal St 310-320

Service and Comfort on the bus from Portland, OR to Chicago

Want to know which seat classes are available on the buses from Portland, OR to Chicago? Or which bus companies serve the route Portland, OR to Chicago? Below you will find answers to your questions.

FAQs about the Portland, OR to Chicago bus

How much does a Portland, OR Chicago bus trip cost?

This depends on, among other things, the day and time of travel. The cheapest trip is available from $227 and takes 64h 35m to reach Chicago. Compare offers to save money!

How much could I save by comparing buses from Portland, OR to Chicago?

This route is offered by 2 companies with a range of ticket prices between $227 and $448. Thus, we recommend booking your ticket as early as possible to make sure you get the cheapest bus ticket to Chicago.

On average, how many connections are available from Portland, OR to Chicago each day?

Every day, the Portland, OR to Chicago bus route is served by approximately 4 connections. With our search, you can compare bus times to find the perfect trip.

How long does a bus journey from Portland, OR to Chicago take?

The fastest bus from Portland, OR to Chicago is offered by Greyhound US and takes 62h 20m. Bus tickets for this connection cost $301. In this context, bear in mind that the journey can take longer due to traffic.

What time is the first bus from Portland, OR to Chicago?

The earliest bus arriving in Chicago from Portland, OR starts at 2:00 AM. However, information regarding departure times may differ on weekends and holidays. Simply use our search to find exact times for your planned travel date.

What time is the last bus from Portland, OR to Chicago?

The latest bus trip departing from Portland, OR for Chicago starts at 8:00 PM. Please note that departure times may differ on weekends and holidays. So just use our search to find the exact times for your planned travel date.

Which bus companies operate the Portland, OR Chicago route?

When traveling by bus from Portland, OR to Chicago, passengers can travel with Greyhound US and FlixBus. With our search, you can compare all available bus tickets to book the one that works for you.

Is there a direct bus between Portland, OR and Chicago?

You can check all the direct connections between Portland, OR and Chicago by using our search and looking at the Changes section in our filters. These are some of the companies which offer a direct bus: Greyhound US and FlixBus.

What can I take with me on the Portland, OR to Chicago bus route?

Depending on which provider you travel with, what you're allowed to bring with you can vary. Generally, you can take a suitcase and hand luggage with you on the Portland, OR Chicago bus route free of charge. Simply use our search to find a bus that is best suited to your needs for your planned travel date.

What equipment is available for the Portland, OR Chicago bus route?

The equipment on board differs depending on the provider. However, many long-distance buses have WiFi so you can tell your friends your exact location during the journey. To make traveling even more pleasant, air conditioning systems provide ventilation. It is best to use our search to get precise information about the equipment of the bus from Portland, OR to Chicago on your planned travel date.

Available seat classes which are offered on the bus route Portland, OR to Chicago

Economy

The cheapest option available for your ticket, it usually comes with reclinable seats and AC.

More bus routes to Portland, OR and to Chicago

Here’s an overview of the most popular bus routes to Portland, OR and to Chicago. Simply click on the connection of your choice, and you will find all the details about your bus route!