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How to get fromChicago to Gilroyby plane, bus (Flixbus, Greyhound), train, subway, car or bus

Find Transport to Gilroy

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There are 9 ways to get from Chicago to Gilroy by plane, bus (Flixbus, Greyhound), train, subway, car, or bus

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly Chicago Midway International Airport to Norman Y. Mineta San José International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Norman Y. Mineta San José International Airport (SJC)planeMDW - SJC
    8h 30m
    $200–866

  2. Fly Chicago O'Hare International Airport to San Francisco International Airport, Caltrain

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to San Francisco International Airport (SFO)planeORD - SFO
    2. Take the train from Millbrae Caltrain Southbound to San Jose Diridon Caltrain Southboundtrain
    3. Take the train from San Jose Diridon Caltrain Southbound to Gilroy Caltrain Southboundtrain
    9h 44m
    $114–424

  3. Bus

    1. Take the bus from Chicago Bus Station to St Louis Bus Stationbus
    2. Take the bus from St Louis Bus Station to Los Angeles Union Stationbus
    3. Take the bus from Downtown Los Angeles to Gilroybus
    2d 5h
    $235–645

  4. Train, BART

    1. Take the train from Chicago Union Station to RichmondtrainCalifornia Zephyr
    2. Take the subway from Richmond to MilpitassubwayOrange-S
    2d 8h
    $177–2,132

  5. Drive 2,184.6 mi

    1. Drive from Chicago to Gilroycar2,184.6 mi
    33h 42m
    $399–576

  6. Fly Chicago O'Hare International Airport to Norman Y. Mineta San José International Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Norman Y. Mineta San José International Airport (SJC)planeORD - SJC
    8h 57m
    $160–716

  7. Fly Chicago Midway International Airport to Oakland International Airport, BART, bus

    1. Fly from Chicago Midway International Airport (MDW) to Oakland International Airport (OAK)planeMDW - OAK
    2. Take the subway from Coliseum to Berryessa / North San Josesubway
    3. Take the bus from San Jose - King Rd Pink Elephant to Gilroybus
    9h 5m
    $204–888

  8. Fly Chicago Midway International Airport to San Francisco International Airport, Caltrain

    1. Fly from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO)planeMDW - SFO
    2. Take the train from Millbrae Caltrain Southbound to San Jose Diridon Caltrain Southboundtrain
    3. Take the train from San Jose Diridon Caltrain Southbound to Gilroy Caltrain Southboundtrain
    9h 21m
    $134–514

  9. Fly Chicago O'Hare International Airport to Fresno Yosemite International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Fresno Yosemite International Airport (FAT)planeORD - FAT
    2. Take the bus from Fresno, CA to Gilroybus
    10h 54m
    $166–732

Chicago to Gilroy by bus and foot

Calendar10Weekly Services
Duration2d 5hAverage Duration
Ticket$235Cheapest Price
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Questions & Answers

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

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Norman Y. Mineta San José International Airport (SJC) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to Gilroy via St Louis Bus Station, Patsaouras Transit Plaza at Union Station, Spring St & 7th St, and Downtown Los Angeles in around 2d 5h.

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