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How to get fromBend to Chicagoby plane, bus, train or car

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There are 8 ways to get from Bend to Chicago by plane, bus, train, or car

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 Roberts Field-Redmond Municipal Airport to Chicago O'Hare International Airport

    best
    1. Fly from Roberts Field-Redmond Municipal Airport (RDM) to Chicago O'Hare International Airport (ORD)planeRDM - ORD
    8h 7m
    $184–813

  2. Bus, train

    1. Take the bus from Bend Hawthorne Station to Portland Union StationbusBend to Portland Express
    2. Take the train from Portland to Chicago Union StationtrainEmpire Builder
    2d 3h
    $291–1,766

  3. Drive 1,989.7 mi

    1. Drive from Bend to Chicagocar1,989.7 mi
    32h 54m
    $364–525

  4. Amtrak Thruway to Mahlon Sweet Field Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Bend, OR to Jaqua Academic Center - Eugenebus
    2. Fly from Mahlon Sweet Field Airport (EUG) to Chicago O'Hare International Airport (ORD)planeEUG - ORD
    8h 53m
    $210–844

  5. Bus to Portland International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Hawthorne Station, Bend to Portland International Airportbus
    2. Fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW)planePDX - MDW
    9h 21m
    $189–816

  6. Bus to Portland International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Hawthorne Station, Bend to Portland International Airportbus
    2. Fly from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD)planePDX - ORD
    9h 33m
    $259–556

  7. Fly Roberts Field-Redmond Municipal Airport to General Mitchell International Airport, train

    1. Fly from Roberts Field-Redmond Municipal Airport (RDM) to General Mitchell International Airport (MKE)planeRDM - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain
    10h 26m
    $457–2,033

  8. Bus, train via Saint Paul

    1. Take the bus from Bend Hawthorne Station to Portland Union Stationbus
    2. Take the bus from Portland Curbside Bus Stop to Pasco Bus Stopbus
    3. Take the train from Pasco Amtrak Station to St. Paul-Minneapolistrain
    4. Take the bus from Saint Paul Union Depot to Chicago Bus Stationbus
    2d 4h
    $231–686

Bend to Chicago by bus and train

Calendar11Weekly Services
Duration2d 3hAverage Duration
Ticket$291Cheapest Price
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Questions & Answers

What companies run services between Bend, OR, USA and Chicago, IL, USA?

United Airlines, Delta, and two other airlines fly from Roberts Field-Redmond Municipal Airport (RDM) to Chicago O'Hare International Airport (ORD) hourly.

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