Rome2Rio

How to get fromPleasanton to Chicagoby plane, train (Amtrak), train, bus, car or subway

Find Transport to Chicago

See all options

There are 8 ways to get from Pleasanton to Chicago by plane, train (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 Oakland International Airport to Chicago Midway International Airport

    best
    1. Fly from Oakland International Airport (OAK) to Chicago Midway International Airport (MDW)plane plane OAK - MDW
    6h 20m
    $177–813

  2. BART to San Francisco International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the subway from Dublin / Pleasanton to Daly Citysubway subway
    2. Fly from San Francisco International Airport (SFO) to Chicago O'Hare International Airport (ORD)plane plane SFO - ORD
    7h 19m
    $92–385

  3. Train (Amtrak)

    1. Take the train from Richmond to Chicago Union Stationtrain train California Zephyr
    2d 6h
    $606–1,409

  4. Train, bus

    1. Take the train from Pleasanton Station to San Jose Station Diridontrain train Ace
    2. Take the train from San Jose to Los Angelestrain train
    3. Take the bus from El Monte Bus Stop to St Louis Bus Stationbus bus
    4. Take the bus from St Louis Bus Station to Chicago Bus Stationbus bus
    2d 14h
    $464–922

  5. Drive 2,130.4 mi

    1. Drive from Pleasanton to Chicagocar car 2,130.4 mi
    32h 58m
    $389–562

  6. Train to Norman Y. Mineta San José International Airport, fly to Chicago Midway International Airport

    1. Take the train from Pleasanton Station to Santa Clara Stationtrain train
    2. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago Midway International Airport (MDW)plane plane SJC - MDW
    6h 53m
    $213–968

  7. BART to San Francisco International Airport, fly to Chicago Midway International Airport

    1. Take the subway from Dublin / Pleasanton to Daly Citysubway subway
    2. Fly from San Francisco International Airport (SFO) to Chicago Midway International Airport (MDW)plane plane SFO - MDW
    7h 6m
    $147–675

  8. Train to Norman Y. Mineta San José International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Pleasanton Station to Santa Clara Stationtrain train
    2. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago O'Hare International Airport (ORD)plane plane SJC - ORD
    7h 20m
    $123–568

Pleasanton to Chicago by subway and train (Amtrak)

Calendar7Weekly Services
Duration2d 6hAverage Duration
Ticket$606Cheapest Price
See schedules

Questions & Answers

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

Southwest Airlines flies from Oakland International Airport (OAK) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, Amtrak operates a train from Richmond to Chicago Union Station once daily. Tickets cost $600–1,400 and the journey takes 2d 4h.

Airlines
Train operators
Bus 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

Where to next?

Trips from Pleasanton

Trips to Chicago

Popular routes