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How to get fromChicago to Milton-Freewaterby plane, train, bus, bus (Greyhound), or car

Find Transport to Milton-Freewater

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There are 10 ways to get from Chicago to Milton-Freewater by plane, train, bus, bus (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 Chicago O'Hare International Airport to Walla Walla Regional Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Walla Walla Regional Airport (ALW)plane plane ORD - ALW
    11h 55m
    $108–482

  2. Train, bus

    1. Take the train from Chicago Union Station to Pasco Amtrak Stationtrain train Empire Builder
    2. Take the bus from Pasco Intermodal, WA to Valley Transit Centerbus bus East 3 / ...
    45h 2m
    $532–1,314

  3. Bus

    1. Take the bus from Chicago Bus Station to Denver Union Stationbus bus
    2. Take the bus from Denver Union Station to La Grande Bus Stationbus bus
    3. Take the bus from Lagrande Transit Hub to Kayak Transit Hubbus bus
    4. Take the bus from Kayak Transit Hub to Dollar Generalbus bus
    46h 57m
    $324–514

  4. Drive  1,865.5 mi

    1. Drive from Chicago to Milton-Freewatercar car 1,865.5 mi
    31h 35m
    $341–492

  5. Fly Chicago Midway International Airport to Tri-Cities Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Tri-Cities Airport (PSC)plane plane MDW - PSC
    2. Take the bus from Tri-Cities Airport to Valley Transit Centerbus bus
    11h 11m
    $152–629

  6. Fly Chicago O'Hare International Airport to Eastern Oregon Regional Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Eastern Oregon Regional Airport (PDT)plane plane ORD - PDT
    2. Take the bus from Pendleton Airport to Milton-Freewaterbus bus
    10h 13m
    $126–561

  7. Fly Chicago Midway International Airport to Eastern Oregon Regional Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Eastern Oregon Regional Airport (PDT)plane plane MDW - PDT
    2. Take the bus from Pendleton Airport to Milton-Freewaterbus bus
    9h 57m
    $186–811

  8. Fly Chicago O'Hare International Airport to Missoula International Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Missoula International Airport (MSO)plane plane ORD - MSO
    2. Drive from Missoula-Airport-MSO to Milton-Freewatercar car
    11h 59m
    $158–550

  9. Fly Chicago Midway International Airport to Walla Walla Regional Airport

    1. Fly from Chicago Midway International Airport (MDW) to Walla Walla Regional Airport (ALW)plane plane MDW - ALW
    10h 39m
    $158–712

  10. Fly Chicago O'Hare International Airport to Spokane International Airport, train, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Spokane International Airport (GEG)plane plane ORD - GEG
    2. Take the train from Spokane to Pasco Amtrak Stationtrain train
    3. Take the bus from Pasco Intermodal, WA to Valley Transit Centerbus bus
    14h 9m
    $138–550

Chicago to Milton-Freewater by train and bus

Calendar7Weekly Services
Duration45h 2mAverage Duration
Ticket$532Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Milton-Freewater.ExpandLaunch map view
  • Distance: 1,559.2 mi
  • Duration: 11h 55m

What companies run services between Chicago, IL, USA and Milton-Freewater, OR, USA?

Alaska Airlines, Inc., United Airlines, and two other airlines fly from Chicago O'Hare International Airport (ORD) to Walla Walla Regional Airport (ALW) 5 times a day. Alternatively, you can take a bus from Chicago Bus Station to Dollar General via Denver Union Station, Lagrande Transit Hub, and Kayak Transit Hub in around 46h 57m.

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