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How to get fromRedwood City to Chicagoby plane, bus (Greyhound), subway, train, or car

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There are 8 ways to get from Redwood City to Chicago by plane, bus (Greyhound), subway, train, 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 San Francisco International Airport to Chicago Midway International Airport

    best
    1. Fly from San Francisco International Airport (SFO) to Chicago Midway International Airport (MDW)plane plane SFO - MDW
    6h 13m
    $215–462

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

    cheapest
    1. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago O'Hare International Airport (ORD)plane plane SJC - ORD
    7h 4m
    $121–495

  3. Bus

    1. Take the bus from Winslow St & Broadway St to Salesforce Transit Center- Bay 37bus bus Epx
    2. Take the bus from San Francisco Bus Station to Sparks Transit Centerbus bus
    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 3h
    $443–719

  4. BART, train

    1. Take the subway from Millbrae to Richmondsubway subway Red-N
    2. Take the train from Richmond to Chicago Union Stationtrain train California Zephyr
    2d 6h
    $767–1,622

  5. Drive 2,150.3 mi

    1. Drive from Redwood City to Chicagocar car 2,150.3 mi
    33h 21m
    $393–567

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

    1. Fly from San Francisco International Airport (SFO) to Chicago O'Hare International Airport (ORD)plane plane SFO - ORD
    6h 37m
    $135–302

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

    1. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago Midway International Airport (MDW)plane plane SJC - MDW
    6h 35m
    $151–615

  8. Caltrain to Oakland International Airport, fly to Chicago Midway International Airport

    1. Take the train from Redwood City Caltrain Northbound to San Francisco Caltrain Northboundtrain train
    2. Fly from Oakland International Airport (OAK) to Chicago Midway International Airport (MDW)plane plane OAK - MDW
    7h 25m
    $166–623

Redwood City to Chicago by bus

Calendar7Weekly Buses
Duration2d 3hAverage Duration
Ticket$443Cheapest Price
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Questions & Answers

Map of how to get from Redwood City to Chicago.ExpandLaunch map view
  • Distance: 1,876.1 mi
  • Duration: 6h 13m

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

Southwest Airlines and Delta fly from San Francisco International Airport (SFO) to Chicago Midway International Airport (MDW) 4 times a day. Alternatively, you can take a bus from Winslow St & Broadway St to Chicago Bus Station via Salesforce Transit Center- Bay 37, San Francisco Bus Station, Sparks Transit Center, and Denver Union Station in around 2d 3h.

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