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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 9 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
    $230–896

  2. Fly Chicago O'Hare International Airport to Haines Airport, car ferry

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Haines Airport (HNS)plane plane ORD - HNS
    2. Take the carferry from Haines to Skagwaycarferry car ferry
    15h 39m
    $168–673

  3. 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
    $1,482–2,729

  4. Drive  2,908 mi

    1. Drive from Chicago to Skagwaycar car 2,908 mi
    2d 4h
    $531–767

  5. Fly Chicago O'Hare International Airport to Skagway Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Skagway Airport (SGY)plane plane ORD - SGY
    20h 45m
    $182–755

  6. 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
    21h 41m
    $386–1,477

  7. Fly Chicago Midway International Airport to Haines Airport, car ferry

    1. Fly from Chicago Midway International Airport (MDW) to Haines Airport (HNS)plane plane MDW - HNS
    2. Take the carferry from Haines to Skagwaycarferry car ferry
    19h 57m
    $248–1,023

  8. 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 49m
    $336–829

  9. 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
    20h 19m
    $330–1,296

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

Calendar36Weekly Planes
Duration10h 58mAverage Duration
Ticket$191Cheapest 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?

Alaska Airlines, Inc., Air Excursion, and two other airlines fly from Chicago O'Hare International Airport (ORD) to Skagway Airport (SGY) 5 times a day.

Airlines
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Bus operators
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