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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 38m
    $174–757

  2. Train to Los Angeles International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Upland to L.A. Union Stationtrain train
    2. Fly from Los Angeles International Airport (LAX) to Chicago O'Hare International Airport (ORD)plane plane LAX - ORD
    7h 29m
    $106–399

  3. Train via San Bernardino (Amtrak)

    1. Take the train from San Bernardino to Chicago Union Stationtrain train Southwest Chief
    43h 9m
    $276–1,708

  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 / ...
    46h 25m
    $212–349

  5. Drive 1,975.5 mi

    1. Drive from Upland to Chicagocar car 1,975.5 mi
    30h 48m
    $361–521

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

    1. Fly from Ontario International Airport (ONT) to Chicago O'Hare International Airport (ORD)plane plane ONT - ORD
    5h 50m
    $124–557

  7. 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 20m
    $131–519

  8. 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 7m
    $135–572

  9. Train (Amtrak)

    1. Take the train from Ontario Amtrak to Chicago Union Stationtrain train Texas Eagle
    2d 12h
    $260–2,200

Upland to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration43h 9mAverage Duration
Ticket$276Cheapest Price
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Questions & Answers

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) every 4 hours. Alternatively, Amtrak operates a train from San Bernardino to Chicago Union Station once daily. Tickets cost $270–1,700 and the journey takes 41h 39m.

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