Next departures for Oakland to Chicago on November 26
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
West Oakland BART
Downtown Greyhound Station
CheapestFastest
West Oakland BART
Downtown Greyhound Station
No tags
FlixBus + Greyhound Lines, Inc.
UC Berkeley (Crescent Lawn)
Downtown Greyhound Station
No tags
West Oakland BART
537-517 W. Jackson Blvd
No tags
FlixBus + Greyhound Lines, Inc.
UC Berkeley (Crescent Lawn)
537-517 W. Jackson Blvd
No tags
Next departures for Oakland to Chicago on November 27
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
West Oakland BART
Downtown Greyhound Station
CheapestFastest
Greyhound Lines, Inc. + FlixBus
West Oakland BART
Downtown Greyhound Station
No tags
West Oakland BART
537-517 W. Jackson Blvd
No tags
Greyhound Lines, Inc. + FlixBus
West Oakland BART
537-517 W. Jackson Blvd
No tags
Oakland/Berkeley/East Bay
537-517 W. Jackson Blvd
No tags
Next departures for Oakland to Chicago on November 28
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
West Oakland BART
Downtown Greyhound Station
CheapestFastest
Jack London Square
Chicago (Union Station), IL
No tags
Greyhound Lines, Inc. + FlixBus
West Oakland BART
Downtown Greyhound Station
No tags
West Oakland BART
537-517 W. Jackson Blvd
No tags
Emeryville Station
Chicago (Union Station), IL
No tags
Next departures for Oakland to Chicago on November 29
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
West Oakland BART
Downtown Greyhound Station
CheapestFastest
West Oakland BART
Downtown Greyhound Station
No tags
Greyhound Lines, Inc. + FlixBus
West Oakland BART
537-517 W. Jackson Blvd
No tags
West Oakland BART
537-517 W. Jackson Blvd
No tags
Greyhound Lines, Inc. + FlixBus
West Oakland BART
Chicago 95Th & Dan Ryan
No tags
Next departures for Oakland to Chicago on November 30
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
West Oakland BART
Downtown Greyhound Station
CheapestFastest
Jack London Square
Chicago (Union Station), IL
No tags
West Oakland BART
Downtown Greyhound Station
No tags
Greyhound Lines, Inc. + FlixBus
West Oakland BART
537-517 W. Jackson Blvd
No tags
Jack London Square
Chicago (Union Station), IL
No tags
Next departures for Oakland to Chicago on December 1
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
West Oakland BART
537-517 W. Jackson Blvd
Cheapest
West Oakland BART
Downtown Greyhound Station
Fastest
West Oakland BART
Downtown Greyhound Station
No tags
FlixBus + Greyhound Lines, Inc.
UC Berkeley (Crescent Lawn)
Downtown Greyhound Station
No tags
West Oakland BART
537-517 W. Jackson Blvd
No tags
Next departures for Oakland to Chicago on December 2
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
West Oakland BART
Downtown Greyhound Station
CheapestFastest
West Oakland BART
Downtown Greyhound Station
No tags
Greyhound Lines, Inc. + FlixBus
West Oakland BART
537-517 W. Jackson Blvd
No tags
West Oakland BART
537-517 W. Jackson Blvd
No tags
Greyhound Lines, Inc. + FlixBus
Oakland/Berkeley/East Bay
Downtown Greyhound Station
No tags
Last refresh of the prices: Yesterday at 11:14 PM PST.
Compare 2 ways to go from Oakland to Chicago
We recommend taking the train
Among the sustainable travel choices, the train stands out as the good way to reach Chicago. The journey takes about 2 days, 5 hours 27 minutes and with fares starting at just $125, it presents an excellent value for a comfortable ride.
Greyhound Lines offers the most comprehensive intercity bus services in the United States. They operate a modern, environmentally friendly fleet that serves more than 2400 destinations and carries nearly 16 million passengers annually. When traveling with them, you can expect free WiFi, onboard entertainment, bathrooms, power outlets and decent legroom. One of the great perks of Greyhound is that they connect big cities and smaller towns in the US, where you usually can't get to by train or plane. If you're looking for safe and affordable transportation, Greyhound is a great choice.
Based on 5607 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $239
Amtrak Oakland Chicago recent customer reviews
Wish I could go first class I know they had a ball super comfortable and an overall decent ride definitely bringing the kids next time
Flixbus is a European bus operator that offers intercity and bus travel in over 38 countries. Known for their easy-to-spot lime green buses and for offering affordable transportation between cities in Europe and the Americas, Flixbus is a good option for those looking for an affordable, reliable bus company. In their buses, you'll find free WiFi, bathrooms, and power outlets. You can also pay extra to choose your seat and get extra legroom, or even buy a snack or drink onboard directly from the driver. You can reschedule your ticket for a small fee, which varies from $1 to $5, depending on how close you are to the departure date.
Frequently asked questions about traveling from Oakland to Chicago by bus
What is the travel distance from Oakland to Chicago?
The distance separating Oakland and Chicago is 1844 miles (2974 km).
What are the departure and arrival stations when taking the bus from Oakland to Chicago?
The majority of buses traveling from Oakland to Chicago start their journey at West Oakland BART Station and wind up at Downtown Greyhound Station. These are the most popular pick-up and drop-off locations on this route, but you can find others that could fit better into your travel plans.
What are the best sights and things to do in Chicago?
Once in Chicago, you can start exploring the city and discover its surroundings. The top sights and things to do are Chicago Shakespeare Theater on Navy Pier, Lincoln Park Zoo, Lake Michigan, Museum of Science and Industry and Museum of Contemporary Art.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11/23
$296
11/24
$271
Today
$323
11/26
$273
11/27
$228
11/28
$278
11/29
$260
11/30
$322
The cheapest trip from Oakland to Chicago was searched and found on Nov 27, 2025 with a price of $228
To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Oakland to Chicago, as early as possible.
You can expect to pay from $228 to $1,716 for a bus ticket from Oakland to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $228 which is on 2025-11-27.
Usually Amtrak will charge you higher prices for tickets closer to the departure date. To find the best prices, you should be flexible on your date of travel.