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How to get fromSan Jose Airport (SJO) to Chicagoby plane, car, train, or shuttle

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There are 7 ways to get from San Jose Airport (SJO) to Chicago by plane, car, train, 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. Fly to Chicago O'Hare International Airport

    best
    1. Fly from Juan Santamaría International Airport (SJO) to Chicago O'Hare International Airport (ORD)plane plane SJO - ORD
    6h 20m
    $360–542

  2. Fly to Chicago Midway International Airport

    cheapest
    1. Fly from Juan Santamaría International Airport (SJO) to Chicago Midway International Airport (MDW)plane plane SJO - MDW
    7h 46m
    $169–655

  3. Drive 3,283.7 mi

    1. Drive from San-Jose-Airport-SJO to Chicagocar car 3,283.7 mi
    2d 18h
    $709–1,024

  4. Fly to General Mitchell International Airport, train

    1. Fly from Juan Santamaría International Airport (SJO) to General Mitchell International Airport (MKE)plane plane SJO - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    10h 8m
    $280–1,047

  5. Fly to South Bend, train

    1. Fly from Juan Santamaría International Airport (SJO) to South Bend (SBN)plane plane SJO - SBN
    2. Take the train from South Bend Airport to Van Buren St.train train
    11h 2m
    $276–1,032

  6. Fly to Central Illinois Regional Airport At Bloomington-Normal, train

    1. Fly from Juan Santamaría International Airport (SJO) to Central Illinois Regional Airport At Bloomington-Normal (BMI)plane plane SJO - BMI
    2. Take the train from Bloomington-Normal to Chicago Union Stationtrain train
    12h 8m
    $206–749

  7. Fly to Indianapolis, shuttle, train

    1. Fly from Juan Santamaría International Airport (SJO) to Indianapolis (IND)plane plane SJO - IND
    2. Take a shuttle bus from Indianapolis Airport to Holiday Inn City Centreshuttle bus
    3. Take the train from Lafayette Amtrak Station to Chicago Union Stationtrain train
    13h 17m
    $285–1,045

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

Calendar46Weekly Planes
Duration8h 51mAverage Duration
Ticket$142Cheapest Price
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Questions & Answers

Map of how to get from San Jose Airport (SJO) to Chicago.ExpandLaunch map view
  • Distance: 2,238.7 mi
  • Duration: 6h 20m

What companies run services between San Jose Airport (SJO), Costa Rica and Chicago, IL, USA?

United Airlines, American Airlines, and three other airlines fly from Juan Santamaría International Airport (SJO) to Chicago O'Hare International Airport (ORD) every 4 hours.

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