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How to get fromGilroy to Chicagoby plane, bus (Greyhound, Flixbus), bus, subway, train or car

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There are 8 ways to get from Gilroy to Chicago by plane, bus (Greyhound, Flixbus), bus, subway, train, 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.

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

    best
    1. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago Midway International Airport (MDW)plane plane SJC - MDW
    7h 50m
    $190–866

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

    cheapest
    1. Take the train from Gilroy Caltrain Northbound to San Jose Diridon Caltrain Northboundtrain train
    2. Take the train from San Jose Diridon Caltrain Northbound to Millbrae Caltrain Northboundtrain train
    3. Fly from San Francisco International Airport (SFO) to Chicago O'Hare International Airport (ORD)plane plane SFO - ORD
    8h 14m
    $118–464

  3. Bus

    1. Take the bus from Gilroy, CA McDonalds to Chinatown Metro Station - Los Angeles, CAbus bus
    2. Take the bus from Los Angeles Union Station to St Louis Bus Stationbus bus
    3. Take the bus from St Louis Bus Station to Chicago Bus Stationbus bus
    2d 5h
    $201–465

  4. Bus, BART, train

    1. Take the bus from Gilroy Transit Center to Monterey & Senterbus bus 68
    2. Take the subway from Milpitas to Richmondsubway subway
    3. Take the train from Richmond to Chicago Union Stationtrain train
    2d 8h
    $160–1,616

  5. Drive 2,184.1 mi

    1. Drive from Gilroy to Chicagocar car 2,184.1 mi
    33h 54m
    $399–576

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

    1. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago O'Hare International Airport (ORD)plane plane SJC - ORD
    7h 59m
    $140–616

  7. Caltrain, Caltrain to San Francisco International Airport, fly to Chicago Midway International Airport

    1. Take the train from Gilroy Caltrain Northbound to San Jose Diridon Caltrain Northboundtrain train
    2. Take the train from San Jose Diridon Caltrain Northbound to Millbrae Caltrain Northboundtrain train
    3. Fly from San Francisco International Airport (SFO) to Chicago Midway International Airport (MDW)plane plane SFO - MDW
    7h 52m
    $153–684

  8. Caltrain, train to Oakland International Airport, fly to Chicago Midway International Airport

    1. Take the train from Gilroy Caltrain Northbound to San Jose Diridon Caltrain Northboundtrain train
    2. Take the train from San Jose to Oakland Coliseum/Airport Amtraktrain train
    3. Fly from Oakland International Airport (OAK) to Chicago Midway International Airport (MDW)plane plane OAK - MDW
    8h 44m
    $175–733

Gilroy to Chicago by bus, subway, and train

Calendar7Weekly Services
Duration2d 8hAverage Duration
Ticket$160Cheapest Price
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Questions & Answers

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

Southwest Airlines flies from Norman Y. Mineta San José International Airport (SJC) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, you can take a bus from Gilroy, CA McDonalds to Chicago Bus Station via Chinatown Metro Station - Los Angeles, CA, Chinatown Station, Union Station - Metro A-Line, Los Angeles Union Station, and St Louis Bus Station in around 2d 5h.

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