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How to get fromSkagway to Chicagoby car ferry, plane, train, car, or bus

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There are 6 ways to get from Skagway to Chicago by car ferry, plane, 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. Car ferry to Juneau International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the carferry from Skagway to Juneau, AKcarferry car ferry
    2. Fly from Juneau International Airport (JNU) to Chicago O'Hare International Airport (ORD)plane plane JNU - ORD
    16h 24m
    $168–639

  2. Car ferry, train

    1. Take the carferry from Skagway to Juneau, AKcarferry car ferry
    2. Take the carferry from Juneau to Bellingham, WAcarferry car ferry
    3. Take the train from Bellingham Amtrak Station to Everett Amtrak Stationtrain train
    4. Take the train from Everett Amtrak Station to Chicago Union Stationtrain train
    5d 13h
    $855–2,300

  3. Drive  2,909.8 mi

    1. Drive from Skagway to Chicagocar car 2,909.8 mi
    2d 4h
    $531–767

  4. Bus to Erik Nielsen Whitehorse International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Skagway, AK to Whitehorse, YTbus bus
    2. Fly from Erik Nielsen Whitehorse International Airport (YXY) to Chicago O'Hare International Airport (ORD)plane plane YXY - ORD
    16h 16m
    $364–977

  5. Car ferry to Juneau International Airport, fly to General Mitchell International Airport, train

    1. Take the carferry from Skagway to Juneau, AKcarferry car ferry
    2. Fly from Juneau International Airport (JNU) to General Mitchell International Airport (MKE)plane plane JNU - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    22h 14m
    $289–1,148

  6. Car ferry to Juneau International Airport, fly to Chicago Midway International Airport

    1. Take the carferry from Skagway to Juneau, AKcarferry car ferry
    2. Fly from Juneau International Airport (JNU) to Chicago Midway International Airport (MDW)plane plane JNU - MDW
    17h 9m
    $198–789

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

Calendar28Weekly Planes
Duration11h 7mAverage Duration
Ticket$129Cheapest Price
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Comparing Your Travel Options

Map of how to get from Skagway to Chicago.ExpandLaunch map view
  • Distance: 2,403.7 mi
  • Duration: 16h 24m

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

There is no direct connection from Skagway to Chicago. However, you can take the car ferry to Juneau, AK, take the taxi to Juneau International Airport (JNU) airport, fly to Chicago O'Hare International Airport (ORD), walk to O'Hare, then take the subway to Jackson-Blue. Alternatively, you can take a car ferry from Skagway to Chicago Union Station via Juneau, AK, Juneau, Bellingham, WA, Bellingham Amtrak Station, and Everett Amtrak Station in around 5d 13h.

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