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

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There are 8 ways to get from Bend to Chicago by plane, bus, train, bus (Amtrak, Flixbus, Greyhound), 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)plane plane RDM - ORD
    8h 8m
    $104–473

  2. Bus, train

    1. Take the bus from Bend Hawthorne Station to Portland Union Stationbus bus Bend to Portland Express
    2. Take the train from Portland to Chicago Union Stationtrain train Empire Builder
    2d 3h
    $221–1,166

  3. Amtrak Thruway, bus

    1. Take the bus from Bend, OR to Jaqua Academic Center - Eugenebus bus
    2. Take the bus from Eugene to Sacramento Bus Stationbus bus
    3. Take the bus from Sacramento Bus Station to Sparks Transit Centerbus bus
    4. Take the bus from Sparks Transit Center to Denver Union Stationbus bus
    5. Take the bus from Denver Union Station to Chicago Bus Stationbus bus
    2d 12h
    $237–789

  4. Drive 1,989.6 mi

    1. Drive from Bend to Chicagocar car 1,989.6 mi
    33h 4m
    $364–525

  5. 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 bus
    2. Fly from Mahlon Sweet Field Airport (EUG) to Chicago O'Hare International Airport (ORD)plane plane EUG - ORD
    8h 53m
    $220–894

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

    1. Take the bus from Hawthorne Station, Bend to Portland International Airportbus bus
    2. Fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW)plane plane PDX - MDW
    9h 21m
    $199–916

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

    1. Take the bus from Hawthorne Station, Bend to Portland International Airportbus bus
    2. Fly from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD)plane plane PDX - ORD
    9h 33m
    $149–666

  8. 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)plane plane RDM - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    10h 32m
    $286–1,328

Bend to Chicago by bus and train

Calendar11Weekly Services
Duration2d 3hAverage Duration
Ticket$221Cheapest Price
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Questions & Answers

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

United Airlines, Alaska Airlines, Inc., and two other airlines fly from Roberts Field-Redmond Municipal Airport (RDM) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, you can take a bus from Bend, OR to Chicago Bus Station via Eugene, Sacramento Bus Station, Sparks Transit Center, and Denver Union Station in around 2d 12h.

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