There are 9 ways to get from Chicago to San Jose by plane, train, subway, bus or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner.

Recommended option

Fly Chicago O'Hare to San Jose  •  6 h 29 min

  1. Fly from Chicago O'Hare (ORD) to San Jose (SJC) ORD - SJC

$144 - $457

Cheapest option

Fly Chicago O'Hare to San Francisco, Caltrain  •  7 h 45 min

  1. Fly from Chicago O'Hare (ORD) to San Francisco (SFO) ORD - SFO
  2. Take the Caltrain from Millbrae Caltrain to San Jose Diridon Caltrain

$81 - $327

7 alternative options

Fly Chicago Midway to San Jose  •  6 h 17 min

  1. Fly from Chicago Midway (MDW) to San Jose (SJC) MDW - SJC

$174 - $426

Fly Chicago Midway to Oakland  •  7 h 24 min

  1. Fly from Chicago Midway (MDW) to Oakland (OAK) MDW - OAK

$154 - $618

Fly Chicago O'Hare to Oakland  •  7 h 48 min

  1. Fly from Chicago O'Hare (ORD) to Oakland (OAK) ORD - OAK

$114 - $399

Fly Chicago Midway to San Francisco, Caltrain  •  7 h 36 min

  1. Fly from Chicago Midway (MDW) to San Francisco (SFO) MDW - SFO
  2. Take the Caltrain from Millbrae Caltrain to San Jose Diridon Caltrain

$151 - $406

Train, BART  •  2 days 6 h

  1. Take the train from Chicago Union Station Amtrak to Richmond Transit Station Amtrak California Zephyr
  2. Take the BART from Richmond to Fremont Warm Springs/South Fremont - Richmond

$303 - $887

Bus  •  2 days 7 h

  1. Take the bus from Chicago, Il to Los Angeles, Ca 1351
  2. Take the bus from Los Angeles, Ca to San Jose, Ca 6860 / ...

$238 - $599

Drive  •  33 h 7 min

  1. Drive from Chicago to San Jose 2174 miles

$210 - $310

Questions & Answers

The cheapest way to get from Chicago to San Jose is to fly and Caltrain which costs $80 - $330 and takes 7 h 45 min.

More details

The quickest way to get from Chicago to San Jose is to fly which costs $170 - $430 and takes 6 h 17 min.

More details

The distance between Chicago and San Jose is 1849 miles. The road distance is 2174 miles.

Get driving directions

It takes approximately 6 h 29 min to get from Chicago to San Jose, including transfers.

More details

No, there is no direct bus from Chicago to San Jose. However, there are services departing from Chicago, Il and arriving at San Jose, Ca via Los Angeles, Ca. The journey, including transfers, takes approximately 2 days 7 h.

More details

What companies run services between Chicago, IL, USA and San Jose, CA, USA?

American Airlines, United Airlines and three other airlines fly from Chicago to San Jose hourly. Alternatively, you can take a bus from Chicago to San Jose via Los Angeles, Ca in around 2 days 7 h.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to San Jose
Ave. Duration
4 h 32 min
When
Every day
Estimated price
$270 - $650
Flights from Chicago Midway to San Jose via Denver
Ave. Duration
6 h 5 min
When
Saturday and Sunday
Estimated price
$270 - $650
Flights from Chicago Midway to San Jose via Las Vegas
Ave. Duration
6 h 11 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$270 - $650
Flights from Chicago Midway to San Jose via San Diego
Ave. Duration
6 h 22 min
When
Saturday and Sunday
Estimated price
$270 - $650
Flights from Chicago Midway to San Jose via Santa Ana
Ave. Duration
6 h 25 min
When
Monday to Friday
Estimated price
$270 - $650
Flights from Chicago Midway to San Jose via Los Angeles
Ave. Duration
6 h 30 min
When
Sunday
Estimated price
$270 - $650
Flights from Chicago Midway to San Jose via Salt Lake City
Ave. Duration
6 h 30 min
When
Sunday
Estimated price
$270 - $650
Flights from Chicago Midway to Oakland
Ave. Duration
4 h 30 min
When
Every day
Estimated price
$240 - $700
Flights from Chicago Midway to Oakland via Kansas City
Ave. Duration
5 h 55 min
When
Sunday
Estimated price
$240 - $700
Flights from Chicago Midway to Oakland via Denver
Ave. Duration
6 h 6 min
When
Monday to Saturday
Estimated price
$240 - $700
Flights from Chicago Midway to Oakland via Las Vegas
Ave. Duration
6 h 9 min
When
Every day
Estimated price
$240 - $700
Flights from Chicago Midway to Oakland via St. Louis
Ave. Duration
6 h 20 min
When
Sunday
Estimated price
$240 - $700
Flights from Chicago Midway to San Francisco
Ave. Duration
4 h 35 min
When
Every day
Estimated price
$240 - $800
Flights from Chicago Midway to San Francisco via St. Louis
Ave. Duration
6 h 5 min
When
Saturday
Estimated price
$240 - $800
Flights from Chicago Midway to San Francisco via Denver
Ave. Duration
6 h 18 min
When
Every day
Estimated price
$240 - $800
Flights from Chicago Midway to San Francisco via Las Vegas
Ave. Duration
6 h 20 min
When
Every day
Estimated price
$240 - $800
Flights from Chicago Midway to San Francisco via Phoenix
Ave. Duration
6 h 22 min
When
Saturday and Sunday
Estimated price
$240 - $800
United Airlines
Website
united.com
Flights from Chicago O'Hare to San Jose
Ave. Duration
4 h 35 min
When
Every day
Estimated price
$220 - $800
Flights from Chicago O'Hare to San Jose via Denver
Ave. Duration
6 h 27 min
When
Every day
Estimated price
$220 - $800
Flights from Chicago O'Hare to San Francisco
Ave. Duration
4 h 38 min
When
Every day
Estimated price
$110 - $550
Flights from Chicago O'Hare to San Francisco via Denver
Ave. Duration
6 h 13 min
When
Every day
Estimated price
$110 - $550
American Airlines
Website
aa.com
Flights from Chicago O'Hare to San Jose
Ave. Duration
4 h 29 min
When
Every day
Estimated price
$200 - $800
Flights from Chicago O'Hare to San Jose via Phoenix
Ave. Duration
6 h 35 min
When
Every day
Estimated price
$200 - $800
Flights from Chicago O'Hare to Oakland via Phoenix
Ave. Duration
6 h 41 min
When
Every day
Estimated price
$100 - $700
Flights from Chicago O'Hare to Oakland via Dallas/Ft.Worth
Ave. Duration
7 h 34 min
When
Every day
Estimated price
$100 - $700
Flights from Chicago O'Hare to San Francisco
Ave. Duration
4 h 34 min
When
Every day
Estimated price
$190 - $600
Delta
Website
delta.com
Flights from Chicago O'Hare to San Jose via Salt Lake City
Ave. Duration
6 h 39 min
When
Every day
Estimated price
$230 - $700
Flights from Chicago O'Hare to San Jose via Minneapolis
Ave. Duration
6 h 41 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$230 - $700
Flights from Chicago O'Hare to Oakland via Salt Lake City
Ave. Duration
6 h 34 min
When
Saturday
Estimated price
$130 - $700
Flights from Chicago O'Hare to Oakland via Atlanta
Ave. Duration
8 h 31 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$130 - $700
Alaska Airlines, Inc.
Website
alaskaair.com
Flights from Chicago O'Hare to Oakland via Seattle
Ave. Duration
7 h 52 min
When
Every day
Estimated price
$160 - $650
Flights from Chicago O'Hare to San Francisco
Ave. Duration
4 h 40 min
When
Every day
Estimated price
$190 - $550
Spirit Airlines
Website
spirit.com
Flights from Chicago O'Hare to Oakland
Ave. Duration
4 h 36 min
When
Every day
Estimated price
$210 - $600
Flights from Chicago O'Hare to Oakland via Las Vegas
Ave. Duration
6 h 54 min
When
Every day
Estimated price
$210 - $600
Train operators
Caltrain
Phone
+1 650-508-6200
Website
caltrain.com
Train from Millbrae Caltrain to San Jose Diridon Caltrain
Ave. Duration
45 min
Frequency
Hourly
Estimated price
$7 - $9
Schedules at
caltrain.com
Amtrak
Rome2rio's guide to Amtrak
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Chicago Union Station Amtrak to Richmond Transit Station Amtrak
Ave. Duration
2 days 3 h
Frequency
Once daily
Estimated price
$290 - $900
Website
amtrak.com
Coach Seat
$290 - $430
Flexi Coach Seat
$500 - $750
Business Coach Seat
$600 - $900
Room
$1,100 - $1,600
BART
Website
bart.gov
Subway from Richmond to Fremont
Ave. Duration
1 h 5 min
Frequency
Every 20 minutes
Estimated price
$5 - $7
Schedules at
bart.gov
Bus operators
Greyhound USA
Rome2rio's guide to Greyhound USA
Contact Details
Phone
+1 214-849-8100/1-800-231-2222
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from Chicago, Il to Los Angeles, Ca
Ave. Duration
47 h 55 min
Frequency
Hourly
Estimated price
$200 - $550
Website
greyhound.com
Economy
$200 - $330
Flexible
$390 - $550
Bus from Los Angeles, Ca to San Jose, Ca
Ave. Duration
6 h 45 min
Frequency
Hourly
Estimated price
$35 - $90
Website
greyhound.com
Economy
$35 - $60
Flexible
$70 - $90

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