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How to get fromHighland to Chicagoby plane, train (Amtrak), bus (Greyhound, Flixbus), car, train, or bus

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There are 9 ways to get from Highland to Chicago by plane, train (Amtrak), bus (Greyhound, Flixbus), car, train, or bus

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 Ontario International Airport to Chicago Midway International Airport

    best
    1. Fly from Ontario International Airport (ONT) to Chicago Midway International Airport (MDW)plane plane ONT - MDW
    8h 5m
    $152–619

  2. Fly Ontario International Airport to Chicago O'Hare International Airport

    cheapest
    1. Fly from Ontario International Airport (ONT) to Chicago O'Hare International Airport (ORD)plane plane ONT - ORD
    8h 28m
    $132–429

  3. Train (Amtrak)

    1. Take the train from San Bernardino to Chicago Union Stationtrain train Southwest Chief
    43h 12m
    $702–1,502

  4. Bus

    1. Take the bus from San Bernardino to Montclair Transit Centerbus bus 290
    2. Take the bus from Montclair Transcenter to St Louis Bus Stationbus bus
    3. Take the bus from St Louis Bus Station to Chicago Bus Stationbus bus
    2d 1h
    $334–644

  5. Drive 1,971.9 mi

    1. Drive from Highland to Chicagocar car 1,971.9 mi
    30h 54m
    $360–520

  6. Train to Los Angeles International Airport, fly to Chicago Midway International Airport

    1. Take the train from San Bernardino - Downtown to L.A. Union Stationtrain train
    2. Fly from Los Angeles International Airport (LAX) to Chicago Midway International Airport (MDW)plane plane LAX - MDW
    9h 36m
    $140–684

  7. Bus to John Wayne Airport Orange County, fly to Chicago O'Hare International Airport

    1. Take the bus from San Bernardino to Harbor + Katellabus bus
    2. Fly from John Wayne Airport Orange County (SNA) to Chicago O'Hare International Airport (ORD)plane plane SNA - ORD
    11h 3m
    $199–436

  8. Train to Long Beach Airport, fly to Chicago Midway International Airport

    1. Take the train from San Bernardino - Downtown to L.A. Union Stationtrain train
    2. Fly from Long Beach Airport (LGB) to Chicago Midway International Airport (MDW)plane plane LGB - MDW
    11h 11m
    $159–627

  9. Train, bus to Palm Springs International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from San Bernardino to Fullerton Amtrak Stationtrain train
    2. Take the bus from Fullerton Amtrak Station to Palm Springs Airport Amtrak Bus Stopbus bus
    3. Fly from Palm Springs International Airport (PSP) to Chicago O'Hare International Airport (ORD)plane plane PSP - ORD
    11h 48m
    $218–452

Highland to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration43h 12mAverage Duration
Ticket$702Cheapest Price
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Questions & Answers

Map of how to get from Highland to Chicago.ExpandLaunch map view
  • Distance: 1,741.5 mi
  • Duration: 8h 5m

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

Southwest Airlines flies from Ontario International Airport (ONT) to Chicago Midway International Airport (MDW) 4 times a day. Alternatively, Amtrak operates a train from San Bernardino to Chicago Union Station once daily. Tickets cost $700–1,500 and the journey takes 41h 39m.

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Bus operators

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