Previously seen journeys
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
Greyhound + FlixBus | Bus | Diridon Station | Chicago 95Th & Dan Ryan | No tags | ||||
FlixBus + Greyhound | Bus | Diridon Station | Chicago 95Th & Dan Ryan | No tags | ||||
FlixBus + Greyhound | Bus | Diridon Station | Chicago 95Th & Dan Ryan | No tags | ||||
Greyhound + FlixBus | Bus | Diridon Station | Chicago 95Th & Dan Ryan | No tags | ||||
Greyhound + FlixBus | Bus | Diridon Station | Chicago 95Th & Dan Ryan | No tags |
Compare 2 ways to travel from San Jose to Chicago
Among the sustainable travel choices, the bus stands out as a good way to reach Chicago. The journey takes about 2 days, 13 hours 35 minutes and with fares starting at just R 2 790, it presents an excellent value for a comfortable ride.
Where are the popular stops in San Jose and Chicago?
Stops in San Jose
- A65 Cahill St., San Jose, CA 95110
- B440 S King rd , an Jose CA 95116
- C
1118 E William St
1118 E William St, San Jose, CA 95116, USA - D
San Jose Bus Stop
100 W San Carlos St, San Jose, CA 95113, USA - E
Tamien Station
Guadalupe Fwy, San Jose, CA 95110, USA - F
Diridon Station
65 Cahill St, San Jose, CA 95110, USA
Stops in Chicago
- A630 W Harrison St, Chicago, IL 60607, USA
- B
Chicago O'Hare International Airport
- C
Polk St & Canal St
500-536 W Polk St, Chicago IL 60607, USA - D
Tornado Bus S Kedzie Ave
2807 S Kedzie Ave, Chicago, IL 60623, USA - E
Cumberland CTA
5800 N Cumberland Ave, Chicago, IL 60631, USA - F
Turimex California Ave
2139 S California Ave, Chicago, IL 60608, USA
Compare bus companies
Frequently asked questions about travelling from San Jose, US to Chicago by bus
How much does a bus ticket from San Jose to Chicago cost?
The bus ticket price from San Jose to Chicago starts at R 2 790. The best way to find cheap bus tickets from San Jose to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the bus ride from San Jose to Chicago?
The average travel time between San Jose and Chicago is around 2d 13h, although the fastest bus will take about 2d 5h. This is the time it takes to travel the 2960 km that separates the two cities.
How many daily bus connections are there between San Jose and Chicago?
The number of buses from San Jose to Chicago can differ depending on the day of the week. On average, there are 6 on this route. Some buses run direct routes, while others have layovers. Simplify your bus trip from San Jose to Chicago by comparing and selecting the bus that fits your travel style and budget on Busbud.
Which bus companies travel from San Jose to Chicago?
When taking the bus from San Jose to Chicago, you can travel comfortably and safely with Amtrak, Greyhound, FlixBus.
What are the departure and arrival stations when taking the bus from San Jose to Chicago?
Buses travelling between San Jose and Chicago leave from Diridon Station or Santiago Express San Jose and arrive at Downtown Greyhound Station, Chicago O'Hare International Airport, Polk St & Canal St.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from San Jose, US to Chicago was searched and found on 21 Nov 2025 with a price of R 3 188To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from San Jose, US to Chicago as early as possible.
You can expect to pay from R 3 188 to R 60 924 for a bus ticket from San Jose, US to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at R 3 901, which is on 2025-11-23.
What's the cheapest way to go from San Jose, US to Chicago?
The bus is the cheapest travel choice for this destination
