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

Thursday

Friday

$124

Saturday

$122

Sunday

Monday

$126

Cheapest bus trips Friday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	60h 25m	2:00 AM	Portland, OR	Greyhound Bus Station	4:25 PM	Chicago	Downtown Bus Station	Economy	$124	A Bus from Greyhound US goes from Greyhound Bus Station, Portland, OR (USA) at 5/8/2026 2:00:00 AM to Downtown Bus Station, Chicago (USA) arriving at 5/10/2026 4:25:00 PM. 50 Economy ticket for $124 per person are available. Travel duration is 60h 25m
FlixBus	78h 20m	8:00 PM	Portland, OR	Greyhound Bus Station	4:20 AM	Chicago	Downtown Bus Station	Economy	$127	A Bus from FlixBus goes from Greyhound Bus Station, Portland, OR (USA) at 5/8/2026 8:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 5/12/2026 4:20:00 AM. 50 Economy ticket for $127 per person are available. Travel duration is 78h 20m
FlixBus	82h 0m	8:00 PM	Portland, OR	Greyhound Bus Station	8:00 AM	Chicago	Canal & Van Buren	Economy	$130	A Bus from FlixBus goes from Greyhound Bus Station, Portland, OR (USA) at 5/8/2026 8:00:00 PM to Canal & Van Buren, Chicago (USA) arriving at 5/12/2026 8:00:00 AM. 50 Economy ticket for $130 per person are available. Travel duration is 82h 0m
Greyhound US	76h 0m	2:00 AM	Portland, OR	Greyhound Bus Station	8:00 AM	Chicago	Canal & Van Buren	Economy	$141	A Bus from Greyhound US goes from Greyhound Bus Station, Portland, OR (USA) at 5/8/2026 2:00:00 AM to Canal & Van Buren, Chicago (USA) arriving at 5/11/2026 8:00:00 AM. 50 Economy ticket for $141 per person are available. Travel duration is 76h 0m
FlixBus	79h 20m	8:00 PM	Portland, OR	Greyhound Bus Station	5:20 AM	Chicago	95th Red Line Station	Economy	$216	A Bus from FlixBus goes from Greyhound Bus Station, Portland, OR (USA) at 5/8/2026 8:00:00 PM to 95th Red Line Station, Chicago (USA) arriving at 5/12/2026 5:20:00 AM. 50 Economy ticket for $216 per person are available. Travel duration is 79h 20m

Cheapest bus trips Saturday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	60h 25m	2:00 AM	Portland, OR	Greyhound Bus Station	4:25 PM	Chicago	Downtown Bus Station	Economy	$122	A Bus from Greyhound US goes from Greyhound Bus Station, Portland, OR (USA) at 5/9/2026 2:00:00 AM to Downtown Bus Station, Chicago (USA) arriving at 5/11/2026 4:25:00 PM. 50 Economy ticket for $122 per person are available. Travel duration is 60h 25m
Greyhound US	76h 0m	2:00 AM	Portland, OR	Greyhound Bus Station	8:00 AM	Chicago	Canal & Van Buren	Economy	$134	A Bus from Greyhound US goes from Greyhound Bus Station, Portland, OR (USA) at 5/9/2026 2:00:00 AM to Canal & Van Buren, Chicago (USA) arriving at 5/12/2026 8:00:00 AM. 50 Economy ticket for $134 per person are available. Travel duration is 76h 0m
FlixBus	78h 20m	8:00 PM	Portland, OR	Union Bus Station	4:20 AM	Chicago	Downtown Bus Station	Economy	$143	A Bus from FlixBus goes from Union Bus Station, Portland, OR (USA) at 5/9/2026 8:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 5/13/2026 4:20:00 AM. 50 Economy ticket for $143 per person are available. Travel duration is 78h 20m
FlixBus	82h 0m	8:00 PM	Portland, OR	Union Bus Station	8:00 AM	Chicago	Union Station	Economy	$147	A Bus from FlixBus goes from Union Bus Station, Portland, OR (USA) at 5/9/2026 8:00:00 PM to Union Station, Chicago (USA) arriving at 5/13/2026 8:00:00 AM. 50 Economy ticket for $147 per person are available. Travel duration is 82h 0m
Greyhound US	62h 35m	2:00 AM	Portland, OR	Greyhound Bus Station	6:35 PM	Chicago	95th Red Line Station	Economy	$217	A Bus from Greyhound US goes from Greyhound Bus Station, Portland, OR (USA) at 5/9/2026 2:00:00 AM to 95th Red Line Station, Chicago (USA) arriving at 5/11/2026 6:35:00 PM. 50 Economy ticket for $217 per person are available. Travel duration is 62h 35m

Cheapest bus trips Monday
BertCompanyCountOneCompanyName	Duration	Departure time	From	Departure	Arrival time	To	Destination	Seat classes	Price
Greyhound US	60h 25m	2:00 AM	Portland, OR	Greyhound Bus Station	4:25 PM	Chicago	Downtown Bus Station	Economy	$126	A Bus from Greyhound US goes from Greyhound Bus Station, Portland, OR (USA) at 5/11/2026 2:00:00 AM to Downtown Bus Station, Chicago (USA) arriving at 5/13/2026 4:25:00 PM. 50 Economy ticket for $126 per person are available. Travel duration is 60h 25m
FlixBus	82h 0m	8:00 PM	Portland, OR	Greyhound Bus Station	8:00 AM	Chicago	Canal & Van Buren	Economy	$133	A Bus from FlixBus goes from Greyhound Bus Station, Portland, OR (USA) at 5/11/2026 8:00:00 PM to Canal & Van Buren, Chicago (USA) arriving at 5/15/2026 8:00:00 AM. 50 Economy ticket for $133 per person are available. Travel duration is 82h 0m
Greyhound US	76h 0m	2:00 AM	Portland, OR	Greyhound Bus Station	8:00 AM	Chicago	Canal & Van Buren	Economy	$134	A Bus from Greyhound US goes from Greyhound Bus Station, Portland, OR (USA) at 5/11/2026 2:00:00 AM to Canal & Van Buren, Chicago (USA) arriving at 5/14/2026 8:00:00 AM. 50 Economy ticket for $134 per person are available. Travel duration is 76h 0m
FlixBus	78h 20m	8:00 PM	Portland, OR	Union Bus Station	4:20 AM	Chicago	Downtown Bus Station	Economy	$143	A Bus from FlixBus goes from Union Bus Station, Portland, OR (USA) at 5/11/2026 8:00:00 PM to Downtown Bus Station, Chicago (USA) arriving at 5/15/2026 4:20:00 AM. 50 Economy ticket for $143 per person are available. Travel duration is 78h 20m
FlixBus	79h 20m	8:00 PM	Portland, OR	Greyhound Bus Station	5:20 AM	Chicago	95th Red Line Station	Economy	$218	A Bus from FlixBus goes from Greyhound Bus Station, Portland, OR (USA) at 5/11/2026 8:00:00 PM to 95th Red Line Station, Chicago (USA) arriving at 5/15/2026 5:20:00 AM. 50 Economy ticket for $218 per person are available. Travel duration is 79h 20m

Best Price Offer: The price for the cheapest bus from Portland, OR to Chicago is $114 on 5/13/2026. 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.

Monday is the busiest day, with more than 11 daily buses from Portland, OR to Chicago. Friday has instead the fewest connections, with only 10 daily coaches between Portland, OR and Chicago.

The busiest time of the day is the Night, with 17 buses from Portland, OR to Chicago, while Evening sees the fewest connections between Portland, OR and Chicago, with 15 offers.

Facts about the bus from Portland, OR to Chicago

Compare all providers like Greyhound US and FlixBus that travel 10 times every day by bus from Portland, OR to Chicago in one click! Book your bus ticket from Portland, OR to Chicago starting from $114!

Cheapest Bus	$114
Fastest Bus	62h 25m
Earliest Bus	2:00 AM
Latest Bus	8:00 PM
Daily Bus Routes	10 Ø
Distance	1,754.6 miles
Bus Companies	Greyhound US and FlixBus

Cheapest bus connections from Portland, OR to Chicago

Every day, 10 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 05/05/2026 and for the following days.

Sunday

Monday

Tuesday

Wednesday

Thursday

Friday

Saturday

Sunday 05/03

Monday 05/04

Tuesday 05/05

Wednesday 05/06

Thursday 05/07

Friday 05/08

$130

Saturday 05/09

$122

Sunday 05/10

Monday 05/11

$126

Tuesday 05/12

$225

Wednesday 05/13

$114

Thursday 05/14

$224

Friday 05/15

$137

Saturday 05/16

$126

Sunday 05/17

$226

Monday 05/18

$135

Tuesday 05/19

$226

Wednesday 05/20

$226

Thursday 05/21

Friday 05/22

$155

Saturday 05/23

$234

Sunday 05/24

$133

Monday 05/25

Tuesday 05/26

$114

Wednesday 05/27

$128

Thursday 05/28

$130

Friday 05/29

$232

Saturday 05/30

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 $122, Saturday is the cheapest day for a bus from Portland, OR to Chicago. Monday instead is the most expensive day with prices starting from $126.

Night is the cheapest day time for bus tickets from Portland, OR to Chicago, with $114. Evening is the most expensive time of the day with prices starting from $127.

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.

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

Oregon Convention Center

NE Martin Luther King Jr Blvd 777

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 $114 and takes 62h 25m 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 $114 and $243. 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 10 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 25m. Bus tickets for this connection cost $124. 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.

How does CheckMyBus find the best bus deals from Portland, OR to Chicago?

CheckMyBus collaborates directly with companies around the world to provide you with the best options when searching for a trip. We retrieve their first-hand data to show you real-time prices, schedules, and seat availability for 10 daily trips between Portland, OR and Chicago. With the most up-to-date information from verified sources, you can fairly compare all available options and choose the trip that suits you best.

How does CheckMyBus technology work for trips from Portland, OR to Chicago?

Prices and availability for 10 trips between Portland, OR and Chicago change constantly. To provide you with the most up-to-date information, we connect directly with bus operators, Online Travel Agencies (OTAs), and Global Distribution Systems (GDS) via real-time interfaces (APIs). The data collected from these sources undergoes strict quality checks, is processed within our infrastructure, and is then presented to you on our search results pages. Visit our About Us page to learn more.

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!