Cheap train tickets from Oakland to Chicago

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Trip Summary

There are usually 5 daily train trips available from Oakland to Chicago. Traveling by train from Oakland to Chicago usually takes 60 hours and 26 minutes, but the fastest Amtrak train can make the trip in 52 hours and 31 minutes.

Distance: 1846 mi (2972 km)
Fastest train: 52h 31m
Lowest price: TRY 10,248.16
Trains per day: 0
Most frequent service: Amtrak
Train lines: 1

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Oakland to Chicago Train Schedule

Is it better to travel by bus or train from Oakland to Chicago?

There are usually 1 daily bus trips available from Oakland to Chicago.

	Train	Bus
Avg. Price	Avg. PriceTRY 20,276.23	Avg. PriceTRY 16,125.24Cheaper
Daily Trips	Daily Trips5	Daily Trips1
Duration	Duration60h 26mFaster	Duration61h 30m

There are several train options that can take you from Oakland to Chicago:

Amtrak tickets: TRY 10,248 one-way

See more details

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 TRY 15,128.24. 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 29 days prior to the travel date. You’ll likely pay around TRY 15,437.64 more if you wait to book until the last minute.

Average train ticket prices from Oakland to Chicago by travel date

Over the next 30 days, a one-way train trip from Oakland to Chicago will cost between TRY 11,712 and TRY 16,885. Book in advance to secure the best price in the next few weeks.

Average train ticket prices from Oakland to Chicago by month

Ticket prices for the train from Oakland to Chicago often fluctuate based on the time of year. For the best prices on this route, book in February when the average ticket price is only TRY 14,055. If you're thinking of traveling from Oakland to Chicago during July, keep in mind that train ticket prices may be higher than usual, with an average price of TRY 21,912 during this time of year. The best way to score a cheap deal, even in July, is to book your trip well in advance.

Prices as travel date approaches

By booking your train trip from Oakland to Chicago on Wanderu at least 29 days ahead of time, you can save about TRY 15,437.64 on your ticket. Waiting until the last minute means missing out on these savings!

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 5 trains per day to choose from.

Train	Daily Trips	Avg. Time	Avg. Price
Amtrak	5	60h 26m	TRY 20,276.38

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 Oakland to Chicago every day, as well as 5 trips on the weekends, with prices starting from TRY 10,248.16.

Frequently asked questions about traveling by train from Oakland to Chicago

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 Oakland. If you're not set on traveling by train, you could always take the bus from Oakland to Chicago for TRY 7,343.

Trains per day

Direct trains

The distance between Oakland and Chicago is approximately 1846 miles, or 2972 kilometers. The average train journey between these two cities takes 60 hours and 26 minutes, although the absolute fastest you could get there is 52 hours and 31 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.

Distance (mi)

1846

Distance (km)

2972

The earliest train departs Oakland at 4:35am while the last train of the day leaves at 10:00pm. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.

First train

4:35am

Last train

10:00pm

Trains from Oakland to Chicago are the most crowded on Friday. Tickets also tend to be more expensive then. If you are looking for a great deal on your train tickets or just want extra room to stretch out, consider traveling on Saturday instead, as it tends to be the least crowded day of the week.

Busiest

Friday

Least crowded

Saturday

City Information

Oakland

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?

Main 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?

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

Need a return trip from Chicago to Oakland?

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