- Must visit
Art Institute of Chicago
Major art museum with global collections, notable Impressionist works, and a landmark setting beside Millennium Park.
Cheapest price on 09 Oct
£188
Average ticket price on 09 Oct
£536
Fastest journey on 09 Oct
1 d 22 h
Average journey duration on 09 Oct
2 d 5 h 36 m
Trains on 09 Oct
4
Distance
2823 km
The best way to find a cheap train ticket from Portland, OR to Chicago, IL is to book your journey as far in advance as possible and to avoid travelling at rush hour.
The average ticket from Portland, OR to Chicago, IL will cost around £536 if you buy it on the day, but you can find cheap train tickets today for only £188.
On Fri 09 Oct, we found 4 trains from Portland, OR to Chicago, IL, including 4 direct services.
These direct trains cover the 2823 km distance in an average of 2 d 5 h 36 m but if you time it right, some trains will get you there in just 1 d 22 h .
The slowest trains will take 2 d 22 h 17 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.








Trains from Portland, OR to Chicago, IL run on average 5 times per day, taking around 51h 0m. Cheap train tickets for this journey start at £148 but you can travel from only £73 by flight.
There are 1 trains per day. The earliest train runs at 06:45, the last at 17:09. The fastest train covers the 2823 km distance in 45h 2m.
Distance 2823 km |
Average train duration 51h 0m |
Cheapest ticket price £148 |
Trains per day 5 |
Direct trains 1 |
Fastest train 45h 2m |
First train 6:45 |
Last train 17:09 |
Cheapest Month Nov |
Cheapest Day Sun |
High Season Jan - Mar |
Low Season Apr - Jun |
Busiest Day Wed |
Least Busy Day Wed |
Best time to book 14 days |
The table below shows live departures for Portland, OR to Chicago, IL trains for today, Wednesday 7 October. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Changes | Tickets |
|---|---|---|---|---|---|
![]() | 14:45 Portland, OR | 56h00 | 22:45 Chicago, IL | 0 changesdirect | |
![]() | 22:22 Portland, OR | 70h17 | 20:39 Chicago, IL | 0 changesdirect | |
![]() | 23:45 Portland, OR | 46h00 | 21:45 Chicago, IL | 0 changesdirect | |
| Thursday 8 October | |||||
![]() | 0:45 Portland, OR | 46h00 | 22:45 Chicago, IL | 0 changesdirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
Major art museum with global collections, notable Impressionist works, and a landmark setting beside Millennium Park.
Science museum in Jackson Park with hands-on exhibits, a U-505 submarine, and broad appeal for families and curious adults.
Natural history museum on the Museum Campus, known for dinosaur fossils, gem displays, and wide-ranging science exhibits.
Lively lakefront park with Cloud Gate, gardens, public art, and frequent events at the heart of central Chicago.
Bustling avenue for architecture, shopping, river views, and easy walking between landmark buildings and major attractions.
Scenic pedestrian route along the Chicago River with terraces, bridges, boat access, and excellent close-up architecture views.
Deep-dish pizza is a Chicago classic with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked in a deep pan.
Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers and celery salt.
Italian beef is thinly sliced roast beef on a roll, often dipped in savoury juices and topped with sweet peppers or giardiniera.
Elegant fine-dining restaurant rooted in Midwestern ingredients, with polished service and a refined contemporary dining room.
Historic pizzeria known for classic Chicago deep-dish in a lively, casual setting near the Magnificent Mile.
Long-running counter-service spot famed for Italian beef sandwiches, dipped rolls and spicy giardiniera in a no-frills setting.
Expensive by US city standards: hotels, dining and attractions add up, though buses and the 'L' help keep daily costs manageable.
Tip 18-20% in restaurants, 15-20% for taxis, and $1-2 per drink or coffee in cafés if table service is given.
Find answers to the most common questions about traveling from Portland, OR to Chicago, IL by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

Most Portland, OR to Chicago, IL trains use the Portland Union Station to Union Station station pair. Use this guide to compare Portland, OR and Chicago, IL train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Portland Union Station has practical services for this route, including Wifi, Lockers, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lost and Found Office, Ticket Office, Bike Parking, Bike Rental, Car Rental, Information Desk and Luggage Carts.
Food options include: Wilf's Restaurant & Bar, Al-Amir Lebanese Restaurant
Free. ATMs are available in the train station.
Ticket office support is available at Portland Union Station. Information desks are located in the main hall.
Luggage storage is available at Portland Union Station. Lost and found is available at the station.
Available at Portland Union Station: Parking, Taxis, WC.
Available at Portland Union Station: Bike Parking, Bike Rental, Car Rental.
Accessibility facilities are available at Portland Union Station: Elevators, ramps, restrooms.
Nearby hotels include Embassy Suites by Hilton Portland Downtown, The Benson, a Coast Hotel, Courtyard by Marriott Portland City Center.
Union Station is 3 km from Chicago city centre. Public transport options include:
Union Station has practical services for this route, including Wifi, Lockers, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lounge, Lost and Found Office, Ticket Office, Bike Parking, Car Rental, Information Desk and Luggage Carts.
Food options include: The Chicago Firehouse Restaurant, Lou Mitchell's
Free. ATMs are available in the train station.
Ticket office support is available at Union Station. Information desks are located in the main hall.
Luggage storage is available at Union Station. Lost and found is available at the station.
Available at Union Station: Parking, Taxis, WC.
Available at Union Station: Bike Parking, Car Rental.
Accessibility facilities are available at Union Station: Elevators, ramps, restrooms.
Nearby hotels include The Kimpton Gray Hotel, JW Marriott Chicago, W Chicago - City Center.
Here are some other resources that might have the information you need