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

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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)plane plane MDW - SJC
    8h 35m
    $260–1,216

  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)plane plane ORD - SFO
    2. Take the train from Millbrae Caltrain Southbound to San Jose Diridon Caltrain Southboundtrain train
    3. Take the train from San Jose Diridon Caltrain Southbound to Gilroy Caltrain Southboundtrain train
    9h 48m
    $114–444

  3. Bus

    1. Take the bus from Chicago Bus Station to St Louis Bus Stationbus bus
    2. Take the bus from St Louis Bus Station to Los Angeles Union Stationbus bus
    3. Take the bus from Downtown Los Angeles to Gilroybus bus
    2d 5h
    $238–669

  4. Train, BART

    1. Take the train from Chicago Union Station to Richmondtrain train California Zephyr
    2. Take the subway from Richmond to Milpitassubway subway Orange-S
    2d 8h
    $202–2,075

  5. Drive 2,184.6 mi

    1. Drive from Chicago to Gilroycar car 2,184.6 mi
    33h 51m
    $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)plane plane ORD - SJC
    8h 54m
    $190–866

  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)plane plane MDW - OAK
    2. Take the subway from Coliseum to Berryessa / North San Josesubway subway
    3. Take the bus from San Jose - King Rd Pink Elephant to Gilroybus bus
    9h 25m
    $234–1,038

  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)plane plane MDW - SFO
    2. Take the train from Millbrae Caltrain Southbound to San Jose Diridon Caltrain Southboundtrain train
    3. Take the train from San Jose Diridon Caltrain Southbound to Gilroy Caltrain Southboundtrain train
    9h 41m
    $144–584

  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)plane plane ORD - FAT
    2. Take the bus from Fresno, CA to Gilroybus bus
    10h 50m
    $176–782

Chicago to Gilroy by bus and foot

Calendar10Weekly Services
Duration2d 5hAverage Duration
Ticket$238Cheapest 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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