Cheap train tickets from Oakland 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:
Oakland to Chicago Train Schedule
Trip Summary
6 trains operate daily from Oakland to Chicago. The train trip from Oakland to Chicago is usually about 59 hours and 51 minutes long. However, traveling on the fastest Amtrak train can get you there in as little as 53 hours and 3 minutes.
| Distance | 1846 mi (2972 km) |
| Fastest train | 53h 3m |
| Lowest price | DKK 1,388.23 |
| Most frequent service | Amtrak |
| Train lines | 1 |
What is the price of a train ticket from Oakland to Chicago?
In the last month, the average price of a train ticket from Oakland to Chicago was DKK 1,571.17. Considering the distance between Oakland and Chicago, tickets on this route are relatively expensive. Good news! You can find the cheapest tickets if you book your trip at least 18 days prior to the travel date. You’ll likely pay around DKK 1,129.79 more if you wait to book until the last minute.
Monthly avg. prices
Prices as travel date approaches
Planning ahead pays off when it comes to booking your train trip from Oakland to Chicago. By reserving your ticket on Wanderu at least 18 days before departure, you can save around DKK 1,129.79. Don't miss out on these savings — book in advance!
Which train should you take from Oakland to Chicago?
Amtrak is the one and only train line which connects Oakland to Chicago. However, there are 6 trains per day to choose from.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 6 | 2d 11h 52m | DKK 2,188.54 |
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 6 Amtrak trains from Oakland to Chicago every day, as well as 6 trips on the weekends, with prices starting from DKK 954.
Frequently asked questions about traveling by train from Oakland to Chicago
The distance between Oakland and Chicago is approximately 1846 miles, or 2972 kilometers. The average train journey between these two cities takes 59 hours and 51 minutes, although the absolute fastest you could get there is 53 hours and 3 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.
Thursday tends to be the busiest day of the week with travelers taking trains from Oakland to Chicago. Ticket price also tend to be more expensive on Thursday than other days. If you are hoping to have more room on the train and even save some change check out travel options on Sunday instead, as less people travel then and deals are more likely to be found.
The earliest train departs Oakland at 4:00am while the last train of the day leaves at 9:00pm. 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 6 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 Oakland.
City Information
Oakland
Image credit: Unsplash
Image credit: Unsplash
Image credit: Unsplash
Oakland, CA is a port city that is beginning to step out of the shadow of San Francisco, its neighbor to the west. Every visitor should start their Oakland trip in the downtown area and Old Oakland, the city's historic quarter full of quaint old buildings. While here, don't forget to take a short detour to Oakland's famous Chinatown as well. The African American Museum and Library at Oakland tells the history of Black communities in the area and is definitely worth a stop. For those who would prefer to stay close to nature, Dr. Aurelia Reinhardt Redwood Regional Park's abundance of redwood groves will offer amazing views.
Oakland's food scene is vibrant and diverse, with a wide range of offerings for all budgets. Enssaro is a popular local name with mid-range dishes that will whet your appetite. For an excellent haute-cuisine dinner, head towards The Wolf.
It's easy to get around the Bay Area on local public transit (called the BART, for Bay Area Rapid Transit). Getting to Oakland from further afield is also a breeze thanks to many intercity bus routes in the area and Amtrak's Capitol Corridor train, which stops in Oakland. Flights arrive at the Oakland International Airport, but several additional airport options in the larger Bay Area are also available.
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 Oakland?
Image credit: David Wilson
Link to image attribution
Image credit: David Wilson
Link to image attributionMain departure station: 245 Second St
The Jack London Station in Oakland opened in 1995, replacing 16th Street Station, which was extensively damaged in the Loma Prieta earthquake in 1989. The station was named after the famous writer Jack London, as he spent much of his life in the area. It is a contemporary glass and stone structure located on the easternmost corner of Jack London Square. The square, which fronts a natural estuary leading to San Francisco Bay, was formerly the hub of Oakland's port activities, connecting the maritime and agricultural sectors. It is still an active and bustling waterfront today. Amtrak's Capitol Corridor, Coast Starlight, and Gold Runner trains serve the station. It is the 10th busiest of Amtrak's 74 California stops, boarding or de-boarding an average of 1,142 people per day.
All train stations in Oakland:
245 Second St
Across San Leandro Blvd from BART station - 700 73rd Ave
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
Get around town with Moovit
Need a return trip from Chicago to Oakland?
Search Train TicketsPlan your next adventure
More trains from Oakland
- Oakland to Phoenix
DKK 1,301+
- Oakland to Tucson Train
DKK 949+
- Oakland to Anaheim Train
DKK 585+
- Oakland to Los Angeles Train
DKK 508+
- Oakland to Marysville
DKK 230+
- Train from Oakland to Modesto
DKK 163+
- Train from Oakland to Ontario
DKK 574+
- Train from Oakland to Pasadena
DKK 496+
- Train from Oakland to Salinas
DKK 186+
- Train from Oakland to Santa Rosa
DKK 152+
- Train from Oakland to Suisun
DKK 117+
- Train from Oakland to Ukiah
DKK 206+
- Train from Oakland to Denver
DKK 1,424+
- Train from Oakland to Washington D.C.
DKK 2,925+
- Train from Oakland to Reno
DKK 530+
- Train from Oakland to Eugene
DKK 627+
- Oakland to Klamath Falls Train
DKK 441+
- Oakland to Philadelphia Train
DKK 3,453+
Continue by train from Chicago
- Train from Chicago to Los Angeles
DKK 2,016+
- Chicago to Miami
DKK 1,895+
- Chicago to Carbondale Train
DKK 387+
- Train from Chicago to Springfield
DKK 272+
- Chicago to Michigan City
DKK 195+
- Chicago to Dearborn
DKK 437+
- Chicago to Detroit Train
DKK 443+
- Chicago to Flint Train
DKK 353+
- Chicago to Kalamazoo Train
DKK 288+
- Train from Chicago to New Buffalo
DKK 126+
- Train from Chicago to Saint Paul
DKK 660+
- Train from Chicago to St Louis
DKK 350+
- Chicago to Dallas
DKK 1,091+
- Train from Chicago to Houston
DKK 2,138+
- Chicago to Columbus Train
DKK 274+
- Train from Chicago to Madison
DKK 346+
- Chicago to Milwaukee Train
DKK 180+
Check out these popular routes
- Train from Toronto to Ottawa
DKK 505+
- Montreal to Québec Train
DKK 313+
- Washington D.C. to Boston
DKK 1,508+
- Train from Washington D.C. to New York
DKK 760+
- Train from Chicago to Saint Paul
DKK 660+
- Chicago to Milwaukee Train
DKK 180+
- Train from Boston to Washington D.C.
DKK 1,554+
- Boston to Providence Train
DKK 149+
- Saint Paul to Chicago Train
DKK 633+
- New York to Montreal Train
DKK 587+
- Train from New York to Boston
DKK 857+
- Train from New York to Providence
DKK 777+
- Train from Providence to Boston
DKK 138+
- Seattle to New York Train
DKK 4,431+
- Train from Milwaukee to Chicago
DKK 186+
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.