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How to get fromPebble Beach to Chicagoby shuttle, plane, subway, train or car

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There are 8 ways to get from Pebble Beach to Chicago by shuttle, plane, 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. Shuttle to Norman Y. Mineta San José International Airport, fly to Chicago Midway International Airport

    best
    1. Take a shuttle bus from Monterey Shuttle Station to SJC Airport Terminal Ashuttle bus
    2. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago Midway International Airport (MDW)plane plane SJC - MDW
    7h 45m
    $267–1,039

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

    cheapest
    1. Take a shuttle bus from Monterey Shuttle Station to SFO Airport Internationalshuttle bus
    2. Fly from San Francisco International Airport (SFO) to Chicago O'Hare International Airport (ORD)plane plane SFO - ORD
    8h 54m
    $157–469

  3. Shuttle, BART, train

    1. Take a shuttle bus from Monterey Shuttle Station to SFO Airport Internationalshuttle bus
    2. Take the subway from San Francisco International Airport to Richmondsubway subway
    3. Take the train from Richmond to Chicago Union Stationtrain train
    2d 9h
    $686–1,509

  4. Drive 2,228.8 mi

    1. Drive from Pebble Beach to Chicagocar car 2,228.8 mi
    34h 47m
    $407–588

  5. Shuttle to Norman Y. Mineta San José International Airport, fly to Chicago O'Hare International Airport

    1. Take a shuttle bus from Monterey Shuttle Station to SJC Airport Terminal Ashuttle bus
    2. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago O'Hare International Airport (ORD)plane plane SJC - ORD
    8h 11m
    $187–639

  6. Shuttle to San Francisco International Airport, fly to Chicago Midway International Airport

    1. Take a shuttle bus from Monterey Shuttle Station to SFO Airport Internationalshuttle bus
    2. Fly from San Francisco International Airport (SFO) to Chicago Midway International Airport (MDW)plane plane SFO - MDW
    8h 40m
    $217–749

  7. Shuttle, BART to Oakland International Airport, fly to Chicago Midway International Airport

    1. Take a shuttle bus from Monterey Shuttle Station to SJC Airport Terminal Bshuttle bus
    2. Take the subway from Milpitas to Coliseumsubway subway
    3. Fly from Oakland International Airport (OAK) to Chicago Midway International Airport (MDW)plane plane OAK - MDW
    9h 20m
    $246–903

  8. Fly Monterey Regional Airport to Chicago Midway International Airport

    1. Fly from Monterey Regional Airport (MRY) to Chicago Midway International Airport (MDW)plane plane MRY - MDW
    7h 1m
    $200–838

Norman Y. Mineta San José International Airport (SJC) to Chicago Midway International Airport (MDW) flights

Calendar50Weekly Planes
Duration5h 48mAverage Duration
Ticket$206Cheapest Price
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Questions & Answers

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

American Airlines, Southwest Airlines, and four other airlines fly from Monterey Regional Airport (MRY) to Chicago Midway International Airport (MDW) every 3 hours.

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