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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)planeMDW - ONT
    6h 22m
    $174–757

  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)planeORD - LAX
    2. Take the train from L.A. Union Station to Uplandtrain
    9h 38m
    $106–380

  3. Train via San Bernardino (Amtrak)

    1. Take the train from Chicago Union Station to San BernardinotrainSouthwest Chief
    42h 43m
    $186–582

  4. Bus

    1. Take the bus from Chicago Bus Station to St Louis Bus StationbusFlixBus N2521 / ...
    2. Take the bus from St Louis Bus Station to Montclair TranscenterbusGreyhound US1210
    47h 24m
    $251–523

  5. Drive 1,975.9 mi

    1. Drive from Chicago to Uplandcar1,975.9 mi
    30h 46m
    $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)planeORD - ONT
    6h 49m
    $144–607

  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)planeMDW - LAX
    2. Take the train from L.A. Union Station to Uplandtrain
    9h 18m
    $130–520

  8. Train (Amtrak)

    1. Take the train from Chicago Union Station to Ontario AmtraktrainTexas Eagle
    2d 16h
    $220–2,700

Chicago to Upland by train (Amtrak)

Calendar13Weekly Trains
Duration42h 43mAverage Duration
Ticket$186Cheapest 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 $180–600 and the journey takes 41h 21m.

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