Rome2Rio

How to get fromChicago to Portola Valleyby plane, taxi, bus (Greyhound), train, subway, or car

Find Transport to Portola Valley

See all options

There are 8 ways to get from Chicago to Portola Valley by plane, taxi, bus (Greyhound), 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. Fly Chicago Midway International Airport to Oakland International Airport, taxi

    best
    1. Fly from Chicago Midway International Airport (MDW) to Oakland International Airport (OAK)plane plane MDW - OAK
    2. Take the taxi from Oakland-Airport-OAK to Portola Valleytaxi taxi
    6h 50m
    $352–1,075

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to San Francisco International Airport (SFO)plane plane ORD - SFO
    7h 31m
    $164–338

  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 San Francisco Bus Stationbus bus
    4. Take the bus from Salesforce Transit Center- Bay 37 to Winslow St & Broadway Stbus bus Epx
    2d 4h
    $410–760

  4. Train, BART

    1. Take the train from Chicago Union Station to Richmondtrain train California Zephyr
    2. Take the subway from Richmond to Millbraesubway subway Red-S
    2d 7h
    $828–1,625

  5. Drive 2,160 mi

    1. Drive from Chicago to Portola Valleycar car 2,160 mi
    33h 34m
    $395–570

  6. Fly Chicago Midway International Airport to Norman Y. Mineta San José International Airport

    1. Fly from Chicago Midway International Airport (MDW) to Norman Y. Mineta San José International Airport (SJC)plane plane MDW - SJC
    7h 16m
    $238–899

  7. Fly Chicago Midway International Airport to San Francisco International Airport

    1. Fly from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO)plane plane MDW - SFO
    7h 14m
    $244–498

  8. Fly Chicago O'Hare International Airport to Norman Y. Mineta San José International Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Norman Y. Mineta San José International Airport (SJC)plane plane ORD - SJC
    7h 48m
    $198–599

Chicago Midway International Airport (MDW) to Oakland International Airport (OAK) flights

Calendar33Weekly Planes
Duration6hAverage Duration
Ticket$220Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chicago to Portola Valley.ExpandLaunch map view
  • Distance: 1,886.4 mi
  • Duration: 6h 50m

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

You can take a bus from Chicago Bus Station to Portola Valley via Denver Union Station, Sparks Transit Center, San Francisco Bus Station, Salesforce Transit Center- Bay 37, and Winslow St & Broadway St in around 2d 4h. Alternatively, Southwest Airlines flies from Chicago Midway International Airport (MDW) to Norman Y. Mineta San José International Airport (SJC) 5 times a day.

Airlines
Train operators
Bus operators
Other operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers