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How to get fromChicago to Skagwayby plane, car ferry, train, car, or bus

Find Transport to Skagway

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There are 6 ways to get from Chicago to Skagway by plane, car ferry, train, car, or bus

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 Juneau International Airport, car ferry

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Juneau International Airport (JNU)plane plane ORD - JNU
    2. Take the carferry from Juneau, AK to Skagwaycarferry car ferry
    17h 50m
    $240–896

  2. Train, car ferry

    1. Take the train from Chicago Union Station to Edmondstrain train
    2. Take the train from Edmonds to Bellingham Amtrak Stationtrain train
    3. Take the carferry from Bellingham, WA to Juneaucarferry car ferry
    4. Take the carferry from Juneau, AK to Skagwaycarferry car ferry
    4d 20h
    $821–2,100

  3. Drive  2,907.9 mi

    1. Drive from Chicago to Skagwaycar car 2,907.9 mi
    2d 4h
    $531–767

  4. Train to General Mitchell International Airport, fly to Juneau International Airport, car ferry

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Juneau International Airport (JNU)plane plane MKE - JNU
    3. Take the carferry from Juneau, AK to Skagwaycarferry car ferry
    20h 17m
    $371–1,453

  5. Fly Chicago O'Hare International Airport to Erik Nielsen Whitehorse International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Erik Nielsen Whitehorse International Airport (YXY)plane plane ORD - YXY
    2. Take the bus from Whitehorse, YT to Skagway, AKbus bus
    17h 50m
    $346–929

  6. Fly Chicago Midway International Airport to Juneau International Airport, car ferry

    1. Fly from Chicago Midway International Airport (MDW) to Juneau International Airport (JNU)plane plane MDW - JNU
    2. Take the carferry from Juneau, AK to Skagwaycarferry car ferry
    17h 45m
    $320–1,296

Chicago O'Hare International Airport (ORD) to Juneau International Airport (JNU) flights

Calendar41Weekly Planes
Duration9h 14mAverage Duration
Ticket$202Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Skagway.ExpandLaunch map view
  • Distance: 2,404.3 mi
  • Duration: 17h 50m

What companies run services between Chicago, IL, USA and Skagway, AK, USA?

There is no direct connection from Chicago to Skagway. However, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Juneau International Airport (JNU), take the taxi to Juneau, AK, then take the car ferry to Skagway. Alternatively, you can take a train from Chicago Union Station to Skagway via Edmonds, Bellingham Amtrak Station, Bellingham, WA, Juneau, and Juneau, AK in around 4d 20h.

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