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

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There are 9 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 car ferry 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 16m
    $178–639

  2. Car ferry, train

    1. Take the car ferry from Skagway to Juneau, AKcarferry car ferry
    2. Take the car ferry from Juneau to Bellingham, WAcarferry car ferry
    3. Take the train from Bellingham Amtrak Station to Edmondstrain train
    4. Take the train from Edmonds to Chicago Union Stationtrain train
    5d 14h
    $1,015–2,520

  3. Drive 2,909.8 mi

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

  4. Fly Skagway Airport to Chicago Midway International Airport

    1. Fly from Skagway Airport (SGY) to Chicago Midway International Airport (MDW)plane plane SGY - MDW
    10h 46m
    $204–771

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

    1. Fly from Skagway Airport (SGY) to Chicago O'Hare International Airport (ORD)plane plane SGY - ORD
    11h 50m
    $208–775

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

    1. Take the car ferry from Skagway to Hainescarferry car ferry
    2. Fly from Haines Airport (HNS) to Chicago Midway International Airport (MDW)plane plane HNS - MDW
    13h 49m
    $206–822

  7. 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 7m
    $374–977

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

    1. Take the car ferry 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
    19h 26m
    $326–1,158

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

    1. Take the car ferry from Skagway to Juneau, AKcarferry car ferry
    2. Fly from Juneau International Airport (JNU) to Chicago Midway International Airport (MDW)plane plane JNU - MDW
    16h 8m
    $198–739

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

Calendar53Weekly Planes
Duration10h 31mAverage Duration
Ticket$142Cheapest Price
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Questions & Answers

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

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

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

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