Oakland, CA, USA to Chicago, IL, USA from $59: 9 ways by bus, train, flight or car
Compare Travel Options and Prices
How to Get from Oakland to Chicago: Cheapest, Fastest and Best Way
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$59 - PlaneBest price
2989 kmDistance
6h 3m Fastest
Compare Train, Bus, Flight, and Driving Options
Get detailed, step-by-step directions below for your trip from Oakland to Chicago with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.
Oakland - Chicago operators
Explore transport companies operating between Oakland and Chicago, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.
Website
southwest.com
Plane from Oakland (OAK) to Chicago Midway (MDW)
Average Duration
6h 3mEstimated price
$341-865Plane from San Francisco (SFO) to Chicago Midway (MDW)
Average Duration
6h 22mEstimated price
$61-226Plane from San Francisco (SFO) to Chicago O'Hare (ORD)
Average Duration
6h 43mEstimated price
$121-516Plane from San Jose (SJC) to Chicago Midway (MDW)
Average Duration
6h 22mEstimated price
$59-266Plane from San Jose (SJC) to Chicago O'Hare (ORD)
Average Duration
6h 2mEstimated price
$2666-8657Contact phone
+1-800-872-7245Website
amtrak.com
Train from Emeryville to Chicago Union Station
Average Duration
48h 3mEstimated price
$3413-3414Train from Oakland to Sacramento
Average Duration
1h 58mEstimated price
$2669-610Contact phone
+1-214-849-8100Website
greyhound.com
Bus from Oakland to Bakersfield Train Station
Average Duration
7h 35mEstimated price
$26690-26680Bus from Bakersfield to Las Vegas Amtrak Bus Stop
Average Duration
5h 23mEstimated price
$0-0Bus from Las Vegas S Strip Transit Terminal to St Louis Bus Station
Average Duration
33h 15mEstimated price
$0-0Bus from St Louis Bus Station to Chicago Bus Station
Average Duration
6h 39mEstimated price
$26695-26685Contact phone
+1-510-464-6000Website
bart.gov
Other from 12th Street / Oakland City Center to Milpitas
Average Duration
51mEstimated price
$2667-2668Oakland to Chicago: Overview of Bus, Train, Flight, and Car Trips
Traveling between Oakland and Chicago offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.
🚗 Embark on an epic road trip from sunny Oakland to the vibrant city of Chicago covering a distance of 2138 miles. 🌉
💰 The journey offers a range of price options between $380 to $600 for gas, snacks, and accommodations along the way. Keep an eye out for scenic pit stops and new adventures waiting to be discovered during the 32-hour drive. 🛣️
Average price
$380 - $600
🚆 Embark on a scenic train journey from Oakland to Chicago on a direct route departing from Emeryville and arriving at Chicago Union Station. This relaxing voyage takes approximately 2 days and 3 hours to reach your destination.
🌉 Traverse through beautiful landscapes and charming towns as you cover a distance of 2,412 miles on your way to Chicago. With one transfer along the route, you'll board the Train San Joaquins in Oakland Jack London for a quick 45-minute ride to Martinez before catching the California Zephyr towards Chicago Union Station.
💰 Ticket prices for this unforgettable train adventure can range from $100 to $650, offering a range of options to suit your budget and preferences. Enjoy the convenience and comfort of Amtrak services as you make lasting memories on your journey from the West Coast to the bustling city of Chicago in the heart of the Midwest.
Departure Point
Emeryville station
Arrival Point
Chicago Union Station
🛫 The quickest way to travel from Oakland to Chicago is by taking a direct flight from Oakland Airport to Chicago Midway Airport, which only takes 4 hours and 5 minutes with Southwest Airlines.
🌆 Once you arrive in Chicago, after a flight duration of 6 hours and 3 minutes, you can explore the vibrant city known for its iconic architecture, deep-dish pizza, and cultural attractions.
Departure Point
Oakland Airport
Arrival Point
Chicago Midway Airport
🌉 Covering a distance of approximately 2,665 miles, the bus trip from Oakland to Chicago takes around 2 days and 7 hours, including transfers. With Greyhound USA operating the services, passengers can enjoy a comfortable and convenient travel experience.
Departure Point
Oakland station
Arrival Point
Chicago Bus Station
Frequently asked questions
Find out more about the route from Oakland to Chicago.
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The cheapest way to travel from Oakland to Chicago is by taking a combination of train and flight. This option typically costs between $75 and $650, depending on the specific dates and airlines chosen. The total travel time for this route is around 8 hours and 6 minutes.
The fastest way to travel from Oakland to Chicago is by flying. The flight duration is approximately 6 hours and 3 minutes. Prices for flights can range from $150 to $430, depending on factors such as the airline and time of booking.
The distance between Oakland and Chicago is approximately 2989 kilometers. This distance is measured as the crow flies. If you were to travel by road, the distance would be approximately 3441 kilometers.
There are a few options to travel from Oakland to Chicago without a car. The most convenient and quickest way is to take a train, which takes approximately 2 days and 3 hours. Amtrak's California Zephyr route offers a scenic journey, passing through beautiful landscapes. The ticket prices for this trip range from $100 to $650, depending on the class and availability. Another option is to fly, which takes around 5-6 hours including layovers, with prices generally ranging from $150 to $600.
The travel time from Oakland to Chicago is approximately 6 hours and 3 minutes, including transfers. This can vary depending on the mode of transportation chosen. Flying is generally the fastest option, with non-stop flights taking around 4 hours.
The cheapest way to get from Oakland to Chicago is by taking a train and then flying. This option typically costs between $75 and $650 and will take approximately 8 hours and 6 minutes. Another option is to take a direct flight, which takes around 6 hours and 3 minutes and costs between $150 and $430. Alternatively, you could take a train, which would cost between $100 and $650 and take approximately 2 days and 3 hours, or a bus, which would take around 2 days and 9 hours and cost between $260 and $600.
There are plenty of accommodation options near Chicago. With over 1116+ hotels available, you have a wide range to choose from. Prices for hotels in Chicago start at $58 per night, making it possible to find an option that fits your budget.
Yes, you can drive from Oakland to Chicago. The driving distance is approximately 3441 km, and it would take about 32 hours and 32 minutes without any stops.
Yes, there is no direct bus between Oakland and Chicago. However, you can take a bus from Oakland to Los Angeles Union Station, then transfer to another bus to St. Louis Bus Station, and finally take a bus to Chicago Bus Station. The total journey time, including transfers, is approximately 2 days and 9 hours.
You can catch the bus from Oakland to Chicago at the Oakland station. Bus services, operated by Flixbus USA, provide transportation between these two cities.
The bus from Oakland to Chicago arrives at the Chicago Bus Station. Greyhound USA operates this bus service and provides a convenient and affordable option for travelers. The Chicago Bus Station is centrally located and offers various transportation options for further travel within the city.
To get to Chicago from the airport, you can take the Blue Line train from O'Hare International Airport to downtown Chicago. The train is convenient and affordable, costing around $5 and taking about 45 minutes.
The airline that offers flights between Oakland and Chicago is Southwest Airlines. They operate flights from Oakland Airport to Chicago Midway Airport. Southwest Airlines is a popular choice for this route, as they often offer competitive prices and multiple daily flights. Travelers can easily book their flights with Southwest Airlines to travel between Oakland and Chicago.
The fastest way to travel from Oakland to Chicago is by taking a direct flight. The quickest flight option is from Oakland Airport to Chicago Midway Airport, which takes approximately 4 hours and 5 minutes. Southwest Airlines offers flights on this route, and the prices can range from $151 to $425, depending on the time of booking and other factors. Overall, it takes around 6 hours and 3 minutes to reach Chicago from Oakland by plane.
The flight from Oakland to Chicago typically takes around 4 hours and 5 minutes.
Trains from Oakland to Chicago arrive at Chicago Union Station. This historic train station is located in the heart of downtown Chicago and serves as a major transportation hub for both local and long-distance trains. Chicago Union Station is conveniently located near various attractions, hotels, and public transportation options, making it easy for travelers to navigate the city upon arrival.
Yes, there is a direct train between Oakland and Chicago. The train departs from Emeryville and arrives at Chicago Union Station. The service operates once daily and runs every day. The journey duration is approximately 2 days and 3 hours.
To catch the train from Oakland to Chicago you will need to go to the Emeryville station. This is where the Amtrak train services operate for this route. Emeryville is conveniently located in the Bay Area and can be easily accessed by various transportation options. It is advisable to check the Amtrak website or contact their customer service for specific details and schedules of the Oakland to Chicago train journey.
The cost of a flight from Oakland to Chicago can range from $151 to $425.
The cost of a train ticket from Oakland to Chicago can range from $100 to $650.
The cost of a bus ticket from Oakland to Chicago can range from $269 to $573.
The cost to drive from Oakland to Chicago will vary depending on factors such as fuel prices, vehicle efficiency, and the route taken. On average, you can expect to spend between $380 and $600 for gas and tolls. Keep in mind that this estimate does not include accommodation or food expenses along the way. It's also important to factor in the time it takes to drive, which can range from 30 to 40 hours depending on traffic and breaks.