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Trip Summary
There are usually 5 daily train trips available from Portland to Chicago. Traveling by train from Portland to Chicago usually takes 30 hours and 19 minutes, but the fastest Amtrak train can make the trip in 25 hours and 42 minutes.
| Distance | 888 mi (1429 km) |
| Fastest train | 25h 42m |
| Lowest price | $123.00 |
| Most frequent service | Amtrak |
| Train lines | 1 |
Price trends for trains from Portland to Chicago
Average prices by travel date
Monthly average prices
Prices as travel date approaches
Which train should you take from Portland to Chicago?
Amtrak is the one and only train line which connects Portland to Chicago. However, there are 5 trains per day to choose from.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 5 | 1d 6h 20m | $303.13 |
Amtrak is the largest passenger railroad service in America, offering daily intercity trains to hundreds of destinations across the contiguous United States, as well as several cities in Canada. Every Amtrak train comes equipped with comfortable seats with extra legroom, as well as several four-seat areas with tables in the middle. In addition, each car has a freshly cleaned restroom, free WiFi and power outlets at every seat. There are also snack bars where you can purchase drinks or food during your journey. On average, there are 5 Amtrak trains from Portland to Chicago every day, as well as 2 trips on the weekends, with prices starting from $123.
Frequently Asked Questions
Our train partners have implemented several different policies to keep you safe during the COVID-19 pandemic. From limiting vehicle capacity to enhancing cleaning protocols and upgrading air filters, train carriers are committed to maintaining a safe environment. For details on what each company is doing to ensure their fleet remains safe for travel, click here.
Although masks are no longer required on public transportation, we stand behind CDC guidelines that encourage passengers to wear a mask over their nose and mouth while on the train or in stations.
Please visit our COVID-19 Travel Guide for more information on all carrier policies and the latest travel advisories issued by every U.S. state, Canadian province, and European country.
The distance between Portland and Chicago is approximately 888 miles, or 1429 kilometers. The average train journey between these two cities takes 30 hours and 19 minutes, although the absolute fastest you could get there is 25 hours and 42 minutes.
Looking for ways to pass the time? Most trains are equipped with Wi-Fi, which means you can stream music, browse social media or get some work done during your ride. That said, in case your train has a spotty signal, or is among the few without Wi-Fi, we also recommend downloading TV shows and movies to your mobile device in advance of your trip. That way the ride will fly by whatever the Wi-Fi situation.
Friday tends to be the busiest day of the week with travelers taking trains from Portland to Chicago. Ticket price also tend to be more expensive on Friday than other days. If you are hoping to have more room on the train and even save some change check out travel options on Monday instead, as less people travel then and deals are more likely to be found.
The earliest train departs Portland at 3:00am while the last train of the day leaves at 9:00am. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.
There are 5 scheduled trains on most days. Unfortunately, none of them are direct connections, so you will need to disembark from your original train and board a connecting train during your journey. Don't forget to bring your carry-on luggage when you switch trains. In some instances, you may also be responsible for transferring your own checked baggage.
You can also take a train for your return trip from Chicago to Portland.
City Information
Portland
Image credit: Unsplash
Image credit: Unsplash
Image credit: Unsplash
Portland is Maine's largest city and, because of that, the main transportation hub in the state. From Portland, travelers can easily reach destinations such as Boston, Albany, and even Gainesville, Texas, by a combination of buses, trains, and ferries. And there’s plenty to do in the city, even if you’re traveling solo.
Since its foundation in 1786, Portland has recovered from no less than four major fires, creating a fascinating blend of old and new. The dedicated Arts District around upper Congress Street has a smattering of important museum collections, including the Portland Museum of Art, the state's oldest public art institution.
The West End hosts the majority of Portland's historic buildings, creating an olde worlde feel. However, the presence of several well-regarded schools and colleges ensures Portland remains one of the most vibrant small cities in the U.S.
After several years of hardship, the Old Port district has once again become the center of the action. Its attractive cobblestone streets and 19th-century red-brick warehouses now contain a selection of on-trend cafes, bars, and boutique stores. At the same time, it's still possible to watch the time-honored tradition of fishermen unloading their lobster pots onto the foreshore.
East of the downtown area, you'll find Munjoy Hill. It's a district with strong Irish and Italian roots, making it one of the best places in Portland to enjoy the authentic cuisine of Italy. It’s no wonder we named Portland one of our top vacation destinations in Maine.
Chicago
Known for its innovative architecture, cultural contributions to jazz and house music, and of course that irresistible deep-dish pizza, the many sights and experiences in Chicago make it one of the best urban vacation destinations for millennials and a top destination in Illinois.
You can't beat the views of the city and Lake Michigan from the SkyDeck in the Willis Tower; at over 1,300 feet, this is the highest observation deck in the U.S. Snap that classic selfie with the Bean in Millennium Park, then wander the many museums in nearby Grant Park. Navy Pier is a popular tourist hotspot for its parks, restaurants, and attractions right on Lake Michigan, and baseball fans will find paradise in Wrigleyville, home to the Chicago Cubs' Wrigley Field and sports bars galore.
Chicago's enormous parks offer plentiful opportunities for outdoor activities in gorgeous urban settings. Many companies offer kayak rentals or boat tours on the Chicago River, with special tours running on Saint Patrick's Day, when the entire river is dyed green. When you’re ready to buy some souvenirs from your epic trip, hit the big brand stores on the Magnificent Mile, or shop local in neighborhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theater, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.
Chicago is one of the biggest transportation hubs in the Midwest, and provides easy access to nearby destinations ideal for day trips, as well as international travel from two airports. Thanks to plenty of bus and train stations throughout the city, getting to the Windy City is a breeze.
Station Information
Where is the train station in Portland?
Image credit: Terry Ross
Link to image attributionMain departure station: 100 Thompsons Pt Rd
The Portland Transportation Center is located at 100 Thompsons Pt Rd, about two miles from Portland's Old Port area. Concord Coach Lines buses and Amtrak's Downeaster trains en route to Boston or Brunswick stop at this station. Inside the station, you'll find plenty of seating, restrooms, vending machines, and information desks for each travel company. In addition, there is plenty of paid parking in front of the station available to passengers.
All train stations in Portland:
100 Thompsons Pt Rd
Where is the train station in Chicago?
Image credit: Jeramey Jannene
Link to image attribution
Main arrival station: Union Station
The historic Chicago Union Station is the United States' third busiest train station and a hub for 15 Amtrak train lines with destinations throughout the country. The station also serves bus carriers like Greyhound, Indian Trails and Jefferson Lines, and offers connections to Metra commuter lines. Union Station is also just a quick walk to the nearest Chicago L lines. The current station was built in 1925, to replace the original one dating back to 1881, and today wows visitors with its impressive facade, massive columns, and opulent Great Hall. Located right in downtown and adjacent to the Chicago Loop, Union Station is equipped with many services and amenities, including phone charging stations, shops, and various food and drink options.
All train stations in Chicago:
Union Station
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