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San Jose to Chicago, IL, USA - Transfer & Transportation Guides

Find transfer & transportation guides from San Jose to Chicago, IL, USA. How to get from San Jose to Chicago, IL, USA by Flight, Bus, Train.

You can get to Chicago, IL, USA from San Jose by verhicle types below

Flight from San Jose to Chicago, IL, USA Bus from San Jose to Chicago, IL, USA Train from San Jose to Chicago, IL, USA
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Transfer solutions

You have 9 options transfer to Chicago, IL, USA from San Jose below

1. Fly San Jose to Chicago O'Hare
Bus ( 6 min. )

Take a bus from Coleman & Earthquake to San Jose Airport Terminal A.

Open Map More details & check price at Santa Clara VTA
Plane ( 4 hr. 7 min. )

Take a flight from San Jose to Chicago O'Hare.

Open Map Check Flights
Subway ( 44 min. )

Take a subway from O'Hare to Jackson-Blue.

Open Map More details & check price at Chicago Transit (CTA)
Duration 6 hr. 1 min.
Distance 2969 km.
Cost 178 USD
2. Fly San Jose to Chicago Midway
Bus ( 6 min. )

Take a bus from Coleman & Earthquake to San Jose Airport Terminal A.

Open Map More details & check price at Santa Clara VTA
Plane ( 4 hr. 10 min. )

Take a flight from San Jose to Chicago Midway.

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Walk ( 7 min. )

Take a foot from Chicago Midway to Midway.

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Subway ( 23 min. )

Take a subway from Midway to Harold Washington Library.

Open Map More details & check price at Chicago Transit (CTA)
Duration 5 hr. 51 min.
Distance 2972 km.
Cost 348 USD
3. BART to Oakland + fly to Chicago Midway
BART ( 43 min. )

Take a subway from Berryessa / North San Jose to Coliseum.

Open Map More details & check price at BART
BART ( 8 min. )

Take a subway from Coliseum to Oakland International Airport Station.

Open Map More details & check price at BART
Plane ( 4 hr. 5 min. )

Take a flight from Oakland to Chicago Midway.

Open Map Check Flights
Walk ( 7 min. )

Take a foot from Chicago Midway to Midway.

Open Map
Subway ( 23 min. )

Take a subway from Midway to Harold Washington Library.

Open Map More details & check price at Chicago Transit (CTA)
Duration 6 hr. 36 min.
Distance 3036 km.
Cost 489 USD
4. BART to Oakland + fly to Chicago O'Hare
BART ( 43 min. )

Take a subway from Berryessa / North San Jose to Coliseum.

Open Map More details & check price at BART
BART ( 8 min. )

Take a subway from Coliseum to Oakland International Airport Station.

Open Map More details & check price at BART
Plane ( 4 hr. 11 min. )

Take a flight from Oakland to Chicago O'Hare.

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Subway ( 44 min. )

Take a subway from O'Hare to Jackson-Blue.

Open Map More details & check price at Chicago Transit (CTA)
Duration 6 hr. 55 min.
Distance 3033 km.
Cost 139 USD
5. Caltrain to San Francisco + fly to Chicago O'Hare
Caltrain ( 1 hr. )

Take a train from San Jose Diridon Caltrain to Millbrae Caltrain.

Open Map More details & check price at Caltrain
BART ( 4 min. )

Take a subway from Millbrae to San Francisco International Airport.

Open Map More details & check price at BART
Plane ( 3 hr. 57 min. )

Take a flight from San Francisco to Chicago O'Hare.

Open Map Check Flights
Subway ( 44 min. )

Take a subway from O'Hare to Jackson-Blue.

Open Map More details & check price at Chicago Transit (CTA)
Duration 7 hr. 12 min.
Distance 3050 km.
Cost 142 USD
6. Caltrain to San Francisco + fly to Chicago Midway
Caltrain ( 1 hr. )

Take a train from San Jose Diridon Caltrain to Millbrae Caltrain.

Open Map More details & check price at Caltrain
BART ( 4 min. )

Take a subway from Millbrae to San Francisco International Airport.

Open Map More details & check price at BART
Plane ( 4 hr. 20 min. )

Take a flight from San Francisco to Chicago Midway.

Open Map Check Flights
Walk ( 7 min. )

Take a foot from Chicago Midway to Midway.

Open Map
Subway ( 23 min. )

Take a subway from Midway to Harold Washington Library.

Open Map More details & check price at Chicago Transit (CTA)
Duration 7 hr. 22 min.
Distance 3053 km.
Cost 362 USD
7. BART + train
BART ( 1 hr. 17 min. )

Take a subway from Berryessa / North San Jose to Richmond.

Open Map More details & check price at BART
Train ( 51 hr. 28 min. )

Take a train from Richmond to Chicago Union Station.

Open Map More details & check price at Amtrak
Duration 53 hr. 45 min.
Distance 3933 km.
Cost 269 USD
8. Bus
Bus ( 8 hr. 40 min. )

Take a bus from San Jose to Los Angeles.

Open Map More details & check price at Greyhound USA
Bus ( 45 hr. 25 min. )

Take a bus from Los Angeles to Indianapolis.

Open Map More details & check price at Greyhound USA
Bus ( 3 hr. 55 min. )

Take a bus from Indianapolis to Chicago.

Open Map More details & check price at Greyhound USA
Duration 1 day
Distance 4401 km.
Cost 386 USD
9. Drive
Car ( 33 hr. 8 min. )

Drive a car from San Jose to Chicago.

Open Map
Duration 33 hr. 8 min.
Distance 3477 km.
Cost 213 USD

Find Hotels in Chicago, IL, USA

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About San Jose, CA, USA

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About Chicago, IL, USA

Chicago ( (listen), locally also ), officially the City of Chicago, is the most populous city in the U.S. state of Illinois, and the third-most-populous city in the United States. With an estimated population of 2,693,976 in 2019, it is also the most... Learn more

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