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

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There are 9 ways to get from Pebble Beach to Chicago by shuttle, plane, bus, train, subway, 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
    $178–639

  2. Fly Monterey Regional Airport to Chicago Midway International Airport

    cheapest
    1. Fly from Monterey Regional Airport (MRY) to Chicago Midway International Airport (MDW)plane plane MRY - MDW
    6h 59m
    $150–589

  3. Bus, train

    1. Take the bus from Salinas to Emeryvillebus bus
    2. Take the train from Emeryville to Renotrain train
    3. Take the bus from Sparks Transit Center to Denver Union Stationbus bus
    4. Take the bus from Denver Union Station to Chicago Bus Stationbus bus
    2d 8h
    $426–719

  4. 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
    $638–1,510

  5. Drive  2,228.8 mi

    1. Drive from Pebble Beach to Chicagocar car 2,228.8 mi
    34h 46m
    $407–588

  6. 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 13m
    $158–499

  7. 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
    $248–509

  8. Shuttle to San Francisco International Airport, fly to Chicago O'Hare 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 O'Hare International Airport (ORD)plane plane SFO - ORD
    8h 55m
    $198–379

  9. 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 19m
    $199–653

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

Calendar37Weekly Planes
Duration5h 36mAverage Duration
Ticket$119Cheapest Price
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Comparing Your Travel Options

Map of how to get from Pebble Beach to Chicago.ExpandLaunch map view
  • Distance: 1,927.5 mi
  • Duration: 7h 45m

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

American Airlines, Southwest Airlines, and three other airlines fly from Monterey Regional Airport (MRY) to Chicago Midway International Airport (MDW) 5 times a day.

Airlines
Train operators
Bus operators

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