San Jose, CA, USA to Chicago, IL, USA from $90: 9 ways by bus, train, flight or car
Compare Travel Options and Prices
How to Get from San Jose to Chicago: Cheapest, Fastest and Best Way
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$90 - Train, FlyBest price
2976 kmDistance
5h 53m Fastest
Compare Train, Bus, Flight, and Driving Options
Get detailed, step-by-step directions below for your trip from San Jose 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.
San Jose - Chicago operators
Explore transport companies operating between San Jose and Chicago, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.
Website
southwest.com
Plane from San Jose to Chicago Midway
Average Duration
4h 10mEstimated price
$7585-7586Plane from San Jose to Chicago Midway via Denver
Average Duration
5h 50mEstimated price
$7585-7586Plane from San Jose to Chicago Midway via Las Vegas
Average Duration
6h 14mEstimated price
$7587-7586Plane from San Jose to Chicago Midway via St. Louis
Average Duration
6h 55mEstimated price
$7587-7582Plane from San Jose to Chicago Midway via Dallas
Average Duration
7h 20mEstimated price
$7584-7588Plane from San Jose to Chicago Midway via Salt Lake City
Average Duration
7h 50mEstimated price
$7585-7586Website
united.com
Plane from San Jose to Chicago O'Hare
Average Duration
4h 15mEstimated price
$905-906Plane from San Jose to Chicago O'Hare via Denver
Average Duration
6h 16mEstimated price
$905-906Website
delta.com
Plane from San Jose to Chicago Midway via Minneapolis
Average Duration
8h 46mEstimated price
$7587-902Plane from San Jose to Chicago O'Hare via Salt Lake City
Average Duration
6h 20mEstimated price
$7589-909Plane from San Jose to Chicago O'Hare via Minneapolis
Average Duration
6h 37mEstimated price
$7589-909Contact phone
+1 800-872-7245Website
amtrak.com
Train from San Jose to Sacramento
Average Duration
3h 5mEstimated price
$4658-90Train from Richmond to Chicago Union Station
Average Duration
49h 3mEstimated price
$7581-904Contact phone
+1-510-464-6000Website
bart.gov
Train from Berryessa / North San Jose to Coliseum
Average Duration
43mEstimated price
$4658-4659Train from Berryessa / North San Jose to Richmond
Average Duration
1h 18mEstimated price
$1230-1231Contact phone
+1 (855) 626-8585Website
flixbus.com
Bus from San Jose Downtown to Los Angeles Downtown
Average Duration
6h 45mEstimated price
$4681-7581Contact phone
+1 214-849-8100Website
greyhound.com
Bus from Los Angeles Union Station to Las Vegas S Strip Transit Terminal
Average Duration
5h 45mEstimated price
$12330-12305Bus from Las Vegas S Strip Transit Terminal to St Louis Bus Station
Average Duration
33h 15mEstimated price
$4655-4652Bus from St Louis Bus Station to Chicago Bus Station
Average Duration
6h 39mEstimated price
$12335-46595San Jose to Chicago: Overview of Bus, Train, Flight, and Car Trips
Traveling between San Jose 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 unforgettable adventure from San Jose to Chicago by car, covering a distance of 2174 miles. The journey promises stunning landscapes and thrilling experiences along the way.
💸 Prepare your budget wisely as the prices for driving from San Jose to Chicago range from $390 to $600, depending on factors such as gas prices, tolls, and accommodation choices. Plan ahead to ensure a smooth and cost-effective road trip.
🌆 Arrive in Chicago after approximately 33 hours and 7 minutes of driving, ready to explore the vibrant city known for its iconic skyline, deep-dish pizza, and rich cultural offerings. Your road trip from the West Coast to the Midwest is sure to be a rewarding and memorable experience.
Average price
$390 - $600
🚆 Traveling from San Jose to Chicago by train is an exciting journey that takes approximately 2 days and 5 hours. While there is no direct train, passengers will make a transfer at Richmond before arriving at Chicago Union Station.
🚅 The route covers a distance of 2,469 miles and offers spectacular views along the way. Passengers will first take the Capitol Corridor train from San Jose to Richmond, followed by the California Zephyr train to reach Chicago Union Station.
Departure Point
Berryessa / North San Jose station
Arrival Point
Chicago Union Station
Useful tips for train travellers
• Onboard services on the Amtrak routes from San Jose to Chicago include a variety of catering options. The Amtrak Coast Starlight and the California Zephyr often feature a Dining Car that serves meals, snacks, and beverages. For a more relaxed option, you can also find a Café Car offering lighter fare, including sandwiches and snacks. Be sure to check the menu upon boarding or on their website for any daily specials.
• The Amtrak California Zephyr offers various seating options, including Roomette and Bedroom accommodations for those seeking more privacy and comfort. First Class has access to meals included in your ticket price, while Business Class provides larger seats and complimentary non-alcoholic beverages. Economy Class is available for budget travelers, but keep in mind that food and drink will incur additional costs. Check the Amtrak website to book your preferred seating: amtrak.com
• Once you arrive at Chicago Union Station, it's essential to know that there's a baggage check service available for a small fee, allowing you to explore the city without hauling your luggage. The station has restrooms, but there are no shower facilities available. To get to downtown quickly, take the CTA Blue Line from the station to the city center; it takes approximately 20 minutes and runs frequently. Ensure you have an Ventra card for fare payment, which can be purchased at the station.
🛫 Flying from San Jose to Chicago is convenient with direct flights that take around 4 hours and 10 minutes, making it a quick and efficient journey.
🌆 The total travel time from San Jose to Chicago by plane is approximately 5 hours and 53 minutes. Prices for flights between these two cities can vary, ranging from $103 to $758 depending on the airline and time of booking.
Departure Point
San Jose Airport
Arrival Point
Chicago Midway Airport
🚌 Embark on a journey from San Jose to Chicago by bus, a trip that spans approximately 2 days and 7 hours with multiple transfers along the way. The bus services from San Jose to Chicago are operated by Flixbus USA and Greyhound USA.
🛣️ Route 1 covers a distance of 2,607 miles with 2 transfers, taking you through cities like Los Angeles, St. Louis, and finally arriving at Chicago. Each leg of the journey offers a unique experience with varying travel times, allowing you to explore different locations during the trip.
🌆 Route 2 extends the adventure with a distance of 2,901 miles and 3 transfers, passing through destinations such as Dallas and Detroit before reaching the bustling city of Chicago. Enjoy the scenic views and diverse landscapes as you make your way across the country on this thrilling bus expedition.
Departure Point
San Jose Downtown station
Arrival Point
Chicago Bus Station
Frequently asked questions
Find out more about the route from San Jose to Chicago.
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The cheapest way to travel from San Jose to Chicago is to take the Caltrain to San Francisco International Airport and then fly to Chicago O'Hare International Airport. This option typically costs between $110 to $500, depending on the time of booking and airline choice. The journey usually takes around 7 hours including the train ride and flight time. It is recommended to book in advance to secure the best deals on both train and flight tickets for this route.
The fastest way to travel from San Jose to Chicago is by taking a direct flight. Flights between the two cities typically take around 5 hours and 53 minutes. Several airlines operate direct flights between San Jose International Airport and Chicago O'Hare International Airport, making air travel the quickest option for this route. Ticket prices for flights can vary depending on the time of booking and availability, ranging from approximately $100 to $800 for a one-way journey.
The distance between San Jose and Chicago is approximately 1849 miles. If you were to travel by road, the distance would be longer, totaling about 2173.6 miles. This journey typically takes around 4-5 hours by plane. It's important to consider which mode of transportation best suits your preferences and budget when planning this trip.
To travel from San Jose to Chicago without a car, you can start by taking the BART to the San Francisco International Airport. From SFO, you can catch a flight to Chicago's O'Hare International Airport. Once you arrive in Chicago, you can take a train or a combination of public transportation options to reach your final destination. This journey typically takes around 2 days and 5 hours, with costs ranging from $100 to $700 depending on the specific transportation options and booking timings.
The total travel time from San Jose to Chicago is approximately 5 hours and 53 minutes, including any necessary transfers during the journey. This estimate may vary depending on the mode of transportation chosen and the specific routes taken. Factors such as traffic conditions, flight layovers, and connection times can impact the overall duration of the trip. It's essential to plan ahead and consider these factors when scheduling your travel from San Jose to Chicago.
There are over 1,576 hotels in Chicago, providing a range of accommodation options to suit different budgets and preferences. Prices start at $67 per night for a standard room, though rates may vary depending on the location and amenities offered by each hotel. From luxury hotels in downtown Chicago to budget-friendly options in the suburbs, travelers have a wide selection of places to stay near the city. It is advisable to book accommodations in advance, especially during peak travel seasons, to secure the best rates and availability.
Yes, you can definitely drive from San Jose to Chicago. The driving distance is approximately 2174 miles, and it usually takes about 33 hours and 7 minutes to reach Chicago by car, depending on traffic and road conditions. Be prepared for a long journey, and plan for rest stops and overnight stays along the way to make the trip more comfortable and manageable. Additionally, consider the cost of gas, tolls, and accommodations when planning your road trip from San Jose to Chicago.
There is no direct bus service available from San Jose to Chicago. Travelers can take a combination of bus services with transfers in Los Angeles, Las Vegas, and St. Louis, which takes approximately 2 days and 7 hours. It is advised to check the specific bus schedules and routes for the most up-to-date information on this route. Alternatively, considering other modes of transportation like flying or taking a train may offer more efficient and direct options for this journey.
To catch the bus from San Jose to Chicago you will need to head to the San Jose Downtown station, where Flixbus USA operates its services. From there, you can board the bus that will take you on your journey to Chicago. It is advisable to arrive at the station ahead of the scheduled departure time to ensure a smooth boarding process and secure your seat on the bus.
The San Jose to Chicago bus services, operated by Greyhound USA, arrive at Chicago Bus Station, which is located in the heart of downtown Chicago. The station is conveniently situated near various public transportation options, making it easy for travelers to reach their final destinations within the city. Chicago Bus Station is equipped with amenities such as seating areas, restrooms, and ticketing counters to ensure a comfortable arrival experience for passengers. Upon reaching the station, travelers can easily access taxis, rideshare services, or continue their journey via the city's public transportation system.
Delta and Southwest Airlines are the main carriers that offer flights between San Jose and Chicago. Both airlines operate flights from San Jose Airport to Chicago Midway Airport. Passengers can choose from various flight options provided by Delta and Southwest to find the most convenient schedule and fare for their travel needs. It is advisable to check for any updates or changes in flight schedules through the respective airline websites or travel agencies before booking.
The fastest way to travel from San Jose to Chicago is by taking a direct flight from San Jose Airport to Chicago Midway Airport, which typically takes about 4 hours and 10 minutes. Both Delta and Southwest Airlines provide flights between these two cities. On average, the total flight time to reach Chicago from San Jose is around 5 hours and 53 minutes. Ticket prices for flights between San Jose and Chicago range from $103 to $758, depending on the airline and time of booking.
The flight duration from San Jose to Chicago on a direct flight is approximately 4 hours and 10 minutes. This is the quickest way to travel between the two cities by air. The flight route typically covers a distance of around 1,800 miles. Be sure to check for any potential layovers or connecting flights that may affect the total travel time.
Trains traveling from San Jose to Chicago operated by Amtrak, arrive at Chicago Union Station. Chicago Union Station is a major railway station located in the West Loop Gate neighborhood of Chicago, providing convenient access to downtown attractions. Passengers can easily disembark at this central station and explore the city's iconic landmarks, museums, and dining options. Additionally, Chicago Union Station offers various amenities and services for travelers, making it a convenient and bustling transportation hub.
Unfortunately, there is no direct train between San Jose and Chicago. However, there are train services that depart from Berryessa/North San Jose and arrive at Chicago Union Station via a transfer in Richmond. This journey, with transfers included, typically takes approximately 2 days and 5 hours. It is recommended to check the specific train schedules and routes for the most up-to-date information on the journey.
To catch the train from San Jose to Chicago head to the Berryessa / North San Jose station, where the BART train service operates. This station serves as a convenient starting point for your journey to Chicago. Trains typically depart from this station on their way to Chicago, providing a reliable and comfortable mode of transportation for your trip. Be sure to check the schedule and arrive at the station on time to catch your train to Chicago.
The cost of a flight from San Jose to Chicago typically ranges from $103 to $758, depending on factors such as the airline, time of booking, and availability of seats. Prices can fluctuate, so it's advisable to compare fares across different airlines and booking platforms to find the best deal. Additionally, booking in advance or being flexible with travel dates can help secure a more affordable ticket for the journey between these two cities.
A bus ticket from San Jose to Chicago typically costs between $265 and $578, depending on the time of booking and the bus company. It is advisable to check multiple bus operators to find the best deal. Prices may also fluctuate based on the day of the week and the season of travel. Booking in advance or during off-peak times may help secure a more affordable fare.
The cost of driving from San Jose to Chicago by car typically ranges between $390 and $600, factoring in expenses for fuel, tolls, and accommodation if needed. It's important to consider additional costs such as meals, parking fees, and potential maintenance or repairs. The total expense may vary depending on the route taken, the vehicle's fuel efficiency, and any unexpected circumstances along the way. Make sure to budget accordingly to cover all potential costs during the road trip.