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How to get fromChicago to Healdsburgby plane, bus (Greyhound, Amtrak), train, bus, car, or subway

Find Transport to Healdsburg

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There are 10 ways to get from Chicago to Healdsburg by plane, bus (Greyhound, Amtrak), train, bus, car, or subway

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 Chicago Midway International Airport to Sonoma County Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Sonoma County Airport (STS)plane plane MDW - STS
    10h 13m
    $144–609

  2. Bus

    1. Take the bus from Chicago Bus Station to Denver Union Stationbus bus
    2. Take the bus from Denver Union Station to Sparks Transit Centerbus bus
    3. Take the bus from Sparks Transit Center to Suisun City Bus Stopbus bus
    4. Take the bus from Napa Amtrak Bus Stop to Healdsburg Amtrak Bus Stopbus bus
    2d 5h

  3. Train, bus (Amtrak)

    1. Take the train from Chicago Union Station to Martineztrain train California Zephyr
    2. Take the bus from Martinez to Healdsburg Amtrak Bus Stopbus bus Amtrak Thruway Connecting Service
    2d 7h

  4. Drive  2,141.4 mi

    1. Drive from Chicago to Healdsburgcar car 2,141.4 mi
    33h 26m
    $391–565

  5. Fly Chicago O'Hare International Airport to San Francisco International Airport, bus, train

    1. Fly from Chicago O'Hare International Airport (ORD) to San Francisco International Airport (SFO)plane plane ORD - SFO
    2. Take the bus from San Francisco Airport to Larkspur - dropoffbus bus
    3. Take the train from SMART Larkspur to SMART Windsortrain train
    11h 17m
    $186–317

  6. Fly Chicago Midway International Airport to San Francisco International Airport, bus, train

    1. Fly from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO)plane plane MDW - SFO
    2. Take the bus from San Francisco Airport to Larkspur - dropoffbus bus
    3. Take the train from SMART Larkspur to SMART Windsortrain train
    11h 3m
    $166–487

  7. Fly Chicago Midway International Airport to Oakland International Airport, bus, train

    1. Fly from Chicago Midway International Airport (MDW) to Oakland International Airport (OAK)plane plane MDW - OAK
    2. Take the bus from Oakland International Airport to San Rafaelbus bus
    3. Take the train from SMART San Rafael to SMART Windsortrain train
    11h
    $210–870

  8. Fly Chicago Midway International Airport to Norman Y. Mineta San José International Airport, BART, train

    1. Fly from Chicago Midway International Airport (MDW) to Norman Y. Mineta San José International Airport (SJC)plane plane MDW - SJC
    2. Take the subway from Milpitas to El Cerrito Del Nortesubway subway
    3. Take the train from SMART San Rafael to SMART Windsortrain train
    12h 19m
    $200–837

  9. Fly Chicago Midway International Airport to Sacramento International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Sacramento International Airport (SMF)plane plane MDW - SMF
    2. Take the train from Sacramento to Richmondtrain train
    3. Take the train from SMART San Rafael to SMART Windsortrain train
    13h 22m
    $244–945

  10. Fly Chicago O'Hare International Airport to Sacramento International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Sacramento International Airport (SMF)plane plane ORD - SMF
    2. Take the train from Sacramento to Richmondtrain train
    3. Take the train from SMART San Rafael to SMART Windsortrain train
    13h 35m
    $184–485

Chicago Midway International Airport (MDW) to Sonoma County Airport (STS) flights

Calendar11Weekly Planes
Duration7h 34mAverage Duration
Ticket$140Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Healdsburg.ExpandLaunch map view
  • Distance: 1,873.7 mi
  • Duration: 10h 13m

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

Southwest Airlines, Alaska Airlines, Inc., and Delta fly from Chicago Midway International Airport (MDW) to Sonoma County Airport (STS) twice daily. Alternatively, you can take a bus from Chicago Bus Station to Healdsburg Amtrak Bus Stop via Denver Union Station, Sparks Transit Center, Suisun City Train Depot, and Napa Amtrak Bus Stop in around 2d 5h.

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