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How to get fromSan José to Chicagoby bus, plane, train, car, or shuttle

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There are 7 ways to get from San José to Chicago by bus, plane, train, car, or shuttle

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

  1. Bus to Juan Santamaría International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from Terminal San José Av. 2, C12 Y 14 to 50 m este Del Aeropuertobus bus
    2. Fly from Juan Santamaría International Airport (SJO) to Chicago O'Hare International Airport (ORD)plane plane SJO - ORD
    9h 49m
    $353–557

  2. Bus to Juan Santamaría International Airport, fly to Chicago Midway International Airport

    cheapest
    1. Take the bus from Terminal San José Av. 2, C12 Y 14 to 50 m este Del Aeropuertobus bus
    2. Fly from Juan Santamaría International Airport (SJO) to Chicago Midway International Airport (MDW)plane plane SJO - MDW
    11h 16m
    $163–657

  3. Bus, train

    1. Take the bus from San José to San Salvadorbus bus
    2. Take the bus from San Salvador to Tapachulabus bus
    3. Take the bus from Tapachula to Terminal Central de Autobuses del Nortebus bus
    4. Take the bus from Terminal Central de Autobuses del Norte to Dallasbus bus
    5. Take the train from Dallas to Chicago Union Stationtrain train
    4d 11h
    $714–1,194

  4. Drive 3,292.9 mi

    1. Drive from San José to Chicagocar car 3,292.9 mi
    2d 19h
    $711–1,027

  5. Shuttle, shuttle to Liberia International Airport, fly to Chicago O'Hare International Airport

    1. Take a shuttle bus from Alajuela to Monteverdeshuttle bus
    2. Take a shuttle bus from Monteverde to Liberia Airportshuttle bus
    3. Fly from Liberia International Airport (LIR) to Chicago O'Hare International Airport (ORD)plane plane LIR - ORD
    12h 43m
    $571–1,389

  6. Bus to Juan Santamaría International Airport, fly to General Mitchell International Airport, train

    1. Take the bus from Terminal San José Av. 2, C12 Y 14 to 50 m este Del Aeropuertobus bus
    2. Fly from Juan Santamaría International Airport (SJO) to General Mitchell International Airport (MKE)plane plane SJO - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    13h 37m
    $280–1,076

  7. Shuttle, shuttle to Liberia International Airport, fly to Chicago Midway International Airport

    1. Take a shuttle bus from Alajuela to Monteverdeshuttle bus
    2. Take a shuttle bus from Monteverde to Liberia Airportshuttle bus
    3. Fly from Liberia International Airport (LIR) to Chicago Midway International Airport (MDW)plane plane LIR - MDW
    14h 32m
    $601–1,489

Juan Santamaría International Airport (SJO) to Chicago O'Hare International Airport (ORD) flights

Calendar53Weekly Planes
Duration8h 43mAverage Duration
Ticket$142Cheapest Price
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Questions & Answers

Map of how to get from San José to Chicago.ExpandLaunch map view
  • Distance: 2,294.7 mi
  • Duration: 9h 49m

What companies run services between San José, Costa Rica and Chicago, IL, USA?

There is no direct connection from San José to Chicago. However, you can take the bus to 50 m este Del Aeropuerto, walk to San-Jose-Airport-SJO airport, fly to Chicago O'Hare International Airport (ORD), walk to O'Hare, then take the subway to Jackson-Blue. Alternatively, you can take a bus from San José to Chicago Union Station via San Salvador, San Salvador, Tapachula, Terminal Central de Autobuses del Norte, Cbd East Tc, Houston @ Young - S - Mb, and Dallas in around 4d 11h.

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