Cheap train tickets from Portland to Chicago
Find and compare the best ground travel options in one place.
Millions of travelers trust Wanderu every year to get:
Lowest Prices
We find the cheapest bus & train tickets, so you can wander for less.
Best Travel Options
We partner with 500+ carriers to bring you the most bus & train options.
Quick & Easy Booking
Book trips quickly with a simple, hassle-free checkout – online & on our app.
Fast Customer Support
We don’t monkey around. We respond within minutes to help you out.
See what travelers are saying about Wanderu:
Trip Summary
5 trains operate daily from Portland to Chicago. The train trip from Portland to Chicago is usually about 33 hours and 34 minutes long. However, traveling on the fastest Amtrak train can get you there in as little as 25 hours and 42 minutes.
| Distance | 888 mi (1429 km) |
| Fastest train | 25h 42m |
| Lowest price | $171.00 |
| Most frequent service | Amtrak |
| Train lines | 1 |
What is the price of a train ticket from Portland to Chicago?
Over the past month, a train ticket between Portland, ME and Chicago, IL cost $209.67, on average. Due to the distance between Portland and Chicago, train tickets on this route tend to be relatively pricey. Booking your trip at least 8 days in advance can help you secure tickets at the best price. For same-day bookings, you’ll likely have to pay around $245.58 more.
Monthly avg. prices
Prices as travel date approaches
By booking your train trip from Portland to Chicago on Wanderu at least 8 days ahead of time, you can save about $245.58 on your ticket. Waiting until the last minute means missing out on these savings!
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 9h 35m | $318.45 |
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 4 trips on the weekends, with prices starting from $162.
Frequently asked questions about traveling by train from Portland to Chicago
The distance between Portland and Chicago is approximately 888 miles, or 1429 kilometers. The average train journey between these two cities takes 33 hours and 34 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.
Saturday 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 Saturday 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: Chicago (Union Station), Illinois
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:
Chicago (Union Station), Illinois
Get around town with Moovit
Need a return trip from Chicago to Portland?
Search Train TicketsPlan your next adventure
More trains from Portland
- Train from Portland to Wells
$8+
- Portland to Kansas City Train
$386+
- Train from Portland to St Louis
$291+
- Train from Portland to New York
$140+
- Train from Portland to Rochester
$146+
- Train from Portland to Syracuse
$123+
- Train from Portland to Harrisburg
$248+
- Train from Portland to North Charleston
$403+
- Portland to Seattle
$610+
Continue by train from Chicago
Check out these popular routes
Wanderu is the simplest way to book bus and train travel.
With just a quick search on Wanderu, you can compare bus and train schedules and prices from hundreds of travel companies in one convenient place to find the trip that works best for you. Wanderu’s simple checkout process makes it easy to book cheap bus and train tickets hassle-free. Most importantly, as Wanderu is an official partner of all leading bus and train companies, we always have the best bus and train deals out there.