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

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There are 9 ways to get from Upland to Chicago by plane, train (Amtrak), bus (Greyhound, Flixbus), 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 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
    5h 39m
    $124–557

  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
    6h 3m
    $99–417

  3. Train via San Bernardino (Amtrak)

    1. Take the train from San Bernardino to Chicago Union Stationtrain train Southwest Chief
    43h 9m
    $1,207–1,910

  4. Bus

    1. Take the bus from Montclair Transcenter to St Louis Bus Stationbus bus Greyhound US1210
    2. Take the bus from St Louis Bus Station to Chicago Bus Stationbus bus FlixBus N2521 / ...
    47h 23m
    $367–567

  5. Drive  1,975.5 mi

    1. Drive from Upland to Chicagocar car 1,975.5 mi
    30h 59m
    $361–521

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

    1. Take the train from Upland to L.A. Union Stationtrain train
    2. Fly from Los Angeles International Airport (LAX) to Chicago Midway International Airport (MDW)plane plane LAX - MDW
    7h 37m
    $157–629

  7. Train to Burbank Bob Hope Airport, fly to Chicago Midway International Airport

    1. Take the train from Upland to L.A. Union Stationtrain train
    2. Fly from Burbank Bob Hope Airport (BUR) to Chicago Midway International Airport (MDW)plane plane BUR - MDW
    8h 16m
    $126–506

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

    1. Take the train from Upland to L.A. Union Stationtrain train
    2. Fly from Long Beach Airport (LGB) to Chicago Midway International Airport (MDW)plane plane LGB - MDW
    9h 7m
    $176–772

  9. Train (Amtrak)

    1. Take the train from Ontario Amtrak to Chicago Union Stationtrain train Texas Eagle
    2d 12h
    $1,400–2,300

Upland to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration43h 9mAverage Duration
Ticket$1,207Cheapest Price
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Comparing Your Travel Options

Map of how to get from Upland to Chicago.ExpandLaunch map view
  • Distance: 1,716.8 mi
  • Duration: 5h 39m

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

Southwest Airlines flies from Ontario International Airport (ONT) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, Amtrak operates a train from San Bernardino to Chicago Union Station once daily. Tickets cost $1,200–1,900 and the journey takes 41h 39m.

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Want to know more about travelling around United States

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