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How to get fromChicago to Highlandby plane, train (Amtrak), bus (Flixbus, Greyhound), car, or train

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

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 Ontario International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Ontario International Airport (ONT)plane plane MDW - ONT
    8h 19m
    $182–769

  2. Fly Chicago Midway International Airport to Long Beach Airport, train

    cheapest
    1. Fly from Chicago Midway International Airport (MDW) to Long Beach Airport (LGB)plane plane MDW - LGB
    2. Take the train from L.A. Union Station to San Bernardino - Downtowntrain train
    11h 38m
    $120–457

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to San Bernardinotrain train Southwest Chief
    42h
    $704–1,427

  4. Bus

    1. Take the bus from Chicago Bus Station to St Louis Bus Stationbus bus FlixBus 2510 / ...
    2. Take the bus from St Louis Bus Station to Montclair Transcenterbus bus Greyhound US1210
    2d 1h
    $334–638

  5. Drive 1,973.1 mi

    1. Drive from Chicago to Highlandcar car 1,973.1 mi
    30h 53m
    $361–521

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Ontario International Airport (ONT)plane plane ORD - ONT
    8h 50m
    $162–489

  7. Fly Chicago Midway International Airport to Los Angeles International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Los Angeles International Airport (LAX)plane plane MDW - LAX
    2. Take the train from L.A. Union Station to San Bernardino - Downtowntrain train
    10h 1m
    $140–684

  8. Fly Chicago O'Hare International Airport to John Wayne Airport Orange County, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John Wayne Airport Orange County (SNA)plane plane ORD - SNA
    2. Take the train from Fullerton Amtrak Station to San Bernardinotrain train
    11h 37m
    $212–461

  9. Fly Chicago Midway International Airport to San Diego International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to San Diego International Airport (SAN)plane plane MDW - SAN
    2. Take the train from San Diego to Oceansidetrain train
    3. Take the train from Oceanside to San Bernardino - Downtowntrain train
    12h 9m
    $222–857

Chicago to Highland by train and bus (Amtrak)

Calendar7Weekly Services
Duration42hAverage Duration
Ticket$704Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Highland.ExpandLaunch map view
  • Distance: 1,741 mi
  • Duration: 8h 19m

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

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Ontario International Airport (ONT) 5 times a day. Alternatively, Amtrak operates a train from Chicago Union Station to San Bernardino once daily. Tickets cost $700–1,500 and the journey takes 41h 21m.

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