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

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There are 9 ways to get from Bend to Chicago by plane, bus, train, bus (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 25m
    $144–663

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

    cheapest
    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 31m
    $139–616

  3. 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
    $671–1,466

  4. Bus

    1. Take the bus from Bend Hawthorne Station to Portland Flix/Greyhoundbus bus
    2. Take the bus from Portland Curbside Bus Stop to Pasco Bus Stopbus bus
    3. Take the bus from Pasco Bus Stop to Denver Union Stationbus bus
    4. Take the bus from Denver Union Station to Chicago Bus Stationbus bus
    2d 6h
    $368–756

  5. Drive 1,989.6 mi

    1. Drive from Bend to Chicagocar car 1,989.6 mi
    33h 3m
    $364–525

  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 16m
    $199–816

  7. Bus to Mahlon Sweet Field Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Bend Hawthorne Station to Eugene Amtrak Bus Platformbus bus
    2. Fly from Mahlon Sweet Field Airport (EUG) to Chicago O'Hare International Airport (ORD)plane plane EUG - ORD
    10h 8m
    $216–905

  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 31m
    $388–1,577

  9. Fly Roberts Field-Redmond Municipal Airport to Chicago Midway International Airport

    1. Fly from Roberts Field-Redmond Municipal Airport (RDM) to Chicago Midway International Airport (MDW)plane plane RDM - MDW
    7h 52m
    $204–863

Bend to Chicago by bus and train

Calendar7Weekly Services
Duration2d 3hAverage Duration
Ticket$671Cheapest Price
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Questions & Answers

Map of how to get from Bend to Chicago.ExpandLaunch map view
  • Distance: 1,707.3 mi
  • Duration: 8h 25m

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 Hawthorne Station to Chicago Bus Station via Portland Flix/Greyhound, Portland Curbside Bus Stop, Pasco Bus Stop, and Denver Union Station in around 2d 6h.

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