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

Find Transport to Skagway

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There are 10 ways to get from Chicago to Skagway by plane, train, car ferry, 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 Midway International Airport to Skagway Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Skagway Airport (SGY)plane plane MDW - SGY
    21h 54m
    $332–1,305

  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
    14h 59m
    $188–773

  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
    $841–2,145

  4. Drive  2,907.9 mi

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

  5. Fly Chicago O'Hare International Airport to Juneau International Airport, car ferry

    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
    18h
    $240–946

  6. 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
    12h 26m
    $242–955

  7. 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
    $372–1,455

  8. 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
    23h 22m
    $258–1,023

  9. 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
    $356–929

  10. 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 30m
    $320–1,196

Chicago Midway International Airport (MDW) to Skagway Airport (SGY) flights

Calendar17Weekly Planes
Duration23h 11mAverage Duration
Ticket$329Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Skagway.ExpandLaunch map view
  • Distance: 2,356.9 mi
  • Duration: 21h 54m

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

Southwest Airlines, Alaska Airlines, Inc., and Alaska Seaplane fly from Chicago Midway International Airport (MDW) to Skagway Airport (SGY) twice daily.

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