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

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There are 11 ways to get from Chicago to Healdsburg by plane, bus (Greyhound, Amtrak), train, bus, 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. 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 56m
    $174–759

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

    cheapest
    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 21m
    $114–445

  3. 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 Vallejo Transit Centerbus bus
    4. Take the bus from Vallejo to Healdsburg Amtrak Bus Stopbus bus
    2d 3h

  4. 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

  5. Drive 2,141.4 mi

    1. Drive from Chicago to Healdsburgcar car 2,141.4 mi
    33h 25m
    $391–565

  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 39m
    $144–645

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

    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 Martineztrain train
    3. Take the bus from Martinez to Healdsburg Amtrak Bus Stopbus bus
    12h 24m

  8. Fly Chicago Midway International Airport to Sacramento International Airport, train, bus

    1. Fly from Chicago Midway International Airport (MDW) to Sacramento International Airport (SMF)plane plane MDW - SMF
    2. Take the train from Sacramento to Martineztrain train
    3. Take the bus from Martinez to Healdsburg Amtrak Bus Stopbus bus
    12h 14m

  9. 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 36m
    $246–1,070

  10. Fly Chicago Midway International Airport to Reno/Tahoe International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Reno/Tahoe International Airport (RNO)plane plane MDW - RNO
    2. Take the bus from Reno Amtrak to Vallejo Transit Centerbus bus
    3. Take the bus from Vallejo to Healdsburg Amtrak Bus Stopbus bus
    15h 10m

  11. Fly Chicago O'Hare International Airport to Reno/Tahoe International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Reno/Tahoe International Airport (RNO)plane plane ORD - RNO
    2. Take the bus from Reno Amtrak to Vallejo Transit Centerbus bus
    3. Take the bus from Vallejo to Healdsburg Amtrak Bus Stopbus bus
    15h 38m

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

Calendar15Weekly Planes
Duration8h 24mAverage Duration
Ticket$169Cheapest Price
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Questions & Answers

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

Southwest Airlines, Alaska Airlines, Inc., and American Airlines 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, and Vallejo in around 2d 3h.

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