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

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There are 8 ways to get from Chicago to Upland 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
    6h 22m
    $254–1,207

  2. Fly Chicago O'Hare International Airport to Los Angeles International Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Los Angeles International Airport (LAX)plane plane ORD - LAX
    2. Take the train from L.A. Union Station to Uplandtrain train
    9h 12m
    $118–470

  3. Train via San Bernardino (Amtrak)

    1. Take the train from Chicago Union Station to San Bernardinotrain train Southwest Chief
    42h 43m
    $539–1,189

  4. Bus

    1. Take the bus from Chicago Bus Station to St Louis Bus Stationbus bus FlixBus N2521 / ...
    2. Take the bus from St Louis Bus Station to Montclair Transcenterbus bus Greyhound US1210
    47h 24m
    $350–667

  5. Drive 1,975.9 mi

    1. Drive from Chicago to Uplandcar car 1,975.9 mi
    30h 56m
    $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
    6h 45m
    $164–757

  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 Uplandtrain train
    9h 5m
    $138–630

  8. Train (Amtrak)

    1. Take the train from Chicago Union Station to Ontario Amtraktrain train Texas Eagle
    2d 16h
    $650–1,500

Chicago to Upland by train (Amtrak)

Calendar13Weekly Trains
Duration42h 43mAverage Duration
Ticket$539Cheapest Price
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Questions & Answers

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

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Ontario International Airport (ONT) every 4 hours. Alternatively, Amtrak operates a train from Chicago Union Station to San Bernardino twice daily. Tickets cost $500–1,200 and the journey takes 41h 21m.

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