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How to get fromChicago to San Mateoby plane, bus (Greyhound), train, subway, or car

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There are 8 ways to get from Chicago to San Mateo by plane, 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 San Francisco International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO)plane plane MDW - SFO
    6h 37m
    $184–461

  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
    6h 55m
    $134–301

  3. Bus (Greyhound)

    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
    2d 4h
    $335–657

  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 6h
    $767–1,591

  5. Drive 2,141.8 mi

    1. Drive from Chicago to San Mateocar car 2,141.8 mi
    33h 12m
    $391–565

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

    1. Fly from Chicago Midway International Airport (MDW) to Norman Y. Mineta San José International Airport (SJC)plane plane MDW - SJC
    2. Take the train from Santa Clara Caltrain Northbound to San Mateo Caltrain Northboundtrain train
    7h 25m
    $192–817

  7. Fly Chicago Midway International Airport to Oakland International Airport

    1. Fly from Chicago Midway International Airport (MDW) to Oakland International Airport (OAK)plane plane MDW - OAK
    7h 42m
    $194–822

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Norman Y. Mineta San José International Airport (SJC)plane plane ORD - SJC
    2. Take the train from Santa Clara Caltrain Northbound to San Mateo Caltrain Northboundtrain train
    7h 58m
    $162–467

Chicago to San Mateo by bus (Greyhound)

Calendar7Weekly Buses
Duration2d 4hAverage Duration
Ticket$335Cheapest Price
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Questions & Answers

Map of how to get from Chicago to San Mateo.ExpandLaunch map view
  • Distance: 1,868.6 mi
  • Duration: 6h 37m

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

Southwest Airlines flies from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO) 5 times a day. Alternatively, you can take a bus from Chicago Bus Station to S Delaware St & Cypress Ave via Denver Union Station, Sparks Transit Center, and Mission St & 1st St in around 2d 4h.

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Need to know: Greyhound

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