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San Jose, CA, USA to Chicago, IL, USA from $90: 9 ways by bus, train, flight or car

Compare Travel Options and Prices

from
San Jose, United States of America
to
Chicago, United States of America

How to Get from San Jose to Chicago: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$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.

Company
various
Plane
Average Duration
5h  53m
Estimated price
$103-758
Recommended
Company
various
Train
Plane
Average Duration
9h  32m
Estimated price
$90-465
Cheapest
route map
Distance: 2976 km
Duration: 5h 53m

See more options

Company
various
Train
Plane
Average Duration
7h 
Estimated price
$117-1030
Company
various
Plane
Average Duration
6h  9m
Estimated price
$123-468
Company
various
BART
Plane
Average Duration
6h  37m
Estimated price
$155-479
Company
various
Train
Plane
Average Duration
7h  22m
Estimated price
$1031-1032
Company
various
BART
Train
Average Duration
49h  5m
Estimated price
$1033-1034
Company
various
Bus
Average Duration
49h  7m
Estimated price
$1035-1036
Company
various
Drive
Average Duration
33h  7m
Estimated price
$1037-1038
Browse car rentalsExplore flights

Traveling From San Jose to Chicago

Your journey from San Jose offers a smooth blend of California's innovation and Chicago's cultural vibrancy, showcasing a fascinating contrast between tech-driven landscapes and rich Midwestern traditions.

Best Neighbourhoods in Chicago

Chicago's neighborhoods each offer distinct experiences and attractions for visitors.

Lincoln Park
• Lush parks and botanical gardens abound.
• Hip boutiques and trendy dining spots.
Wicker Park
• Vibrant arts scene with live music venues.
• Eclectic shops and craft breweries line the streets.
South Loop
• Proximity to museums and cultural institutions.
• Scenic views along Lake Michigan's waterfront.

Best Times To Visit Chicago's Attractions

Navigating Chicago's attractions can be a breeze with smart timing.

Millennium Park
Early mornings, especially on weekdays, offer a quieter experience with stunning views.
The Art Institute of Chicago
Visit during late afternoons on Wednesdays for fewer crowds and extended hours.
Navy Pier
Go on weekdays in the late morning to avoid the weekend rush and enjoy serene lake views.

Chicago Weather: What to Expect Year-Round

Chicago experiences a diverse climate with hot summers and cold winters, making spring and fall the most pleasant seasons to visit. Understanding local weather patterns helps you dress appropriately and plan activities, ensuring a more enjoyable travel experience.

Dining Recommendation

For a true taste of Chicago, indulge in deep-dish pizza at Giordano's, where the layers of gooey cheese and savory toppings create a hearty experience unlike the fresh, light flavors often found in San Jose. The vibrant atmosphere and focus on local ingredients give dining in Chicago a distinct charm that enriches your visit.

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.

Plane Show flights
Website
southwest.com

Plane from San Jose to Chicago Midway

Average Duration
4h 10m
Estimated price
$7585-7586

Plane from San Jose to Chicago Midway via Denver

Average Duration
5h 50m
Estimated price
$7585-7586

Plane from San Jose to Chicago Midway via Las Vegas

Average Duration
6h 14m
Estimated price
$7587-7586

Plane from San Jose to Chicago Midway via St. Louis

Average Duration
6h 55m
Estimated price
$7587-7582

Plane from San Jose to Chicago Midway via Dallas

Average Duration
7h 20m
Estimated price
$7584-7588

Plane from San Jose to Chicago Midway via Salt Lake City

Average Duration
7h 50m
Estimated price
$7585-7586
Website
united.com

Plane from San Jose to Chicago O'Hare

Average Duration
4h 15m
Estimated price
$905-906

Plane from San Jose to Chicago O'Hare via Denver

Average Duration
6h 16m
Estimated price
$905-906
Website
delta.com

Plane from San Jose to Chicago Midway via Minneapolis

Average Duration
8h 46m
Estimated price
$7587-902

Plane from San Jose to Chicago O'Hare via Salt Lake City

Average Duration
6h 20m
Estimated price
$7589-909

Plane from San Jose to Chicago O'Hare via Minneapolis

Average Duration
6h 37m
Estimated price
$7589-909
Train Show train routes
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from San Jose to Sacramento

Average Duration
3h 5m
Estimated price
$4658-90

Train from Richmond to Chicago Union Station

Average Duration
49h 3m
Estimated price
$7581-904
Contact phone
+1-510-464-6000
Website
bart.gov

Train from Berryessa / North San Jose to Coliseum

Average Duration
43m
Estimated price
$4658-4659

Train from Berryessa / North San Jose to Richmond

Average Duration
1h 18m
Estimated price
$1230-1231
Bus Show bus routes
Contact phone
+1 (855) 626-8585
Website
flixbus.com

Bus from San Jose Downtown to Los Angeles Downtown

Average Duration
6h 45m
Estimated price
$4681-7581
Contact phone
+1 214-849-8100
Website
greyhound.com

Bus from Los Angeles Union Station to Las Vegas S Strip Transit Terminal

Average Duration
5h 45m
Estimated price
$12330-12305

Bus from Las Vegas S Strip Transit Terminal to St Louis Bus Station

Average Duration
33h 15m
Estimated price
$4655-4652

Bus from St Louis Bus Station to Chicago Bus Station

Average Duration
6h 39m
Estimated price
$12335-46595

San 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.

Trips from San Jose

Trips to Chicago