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

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There are 9 ways to get from Skagway to Chicago 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 Skagway Airport to Chicago Midway International Airport

    best
    1. Fly from Skagway Airport (SGY) to Chicago Midway International Airport (MDW)plane plane SGY - MDW
    13h 6m
    $234–909

  2. Car ferry to Juneau International Airport, fly to Chicago O'Hare International Airport

    cheapest
    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 48m
    $178–689

  3. 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
    $856–2,300

  4. Drive  2,909.8 mi

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

  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
    14h 10m
    $232–871

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

    1. Take the carferry from Skagway to Hainescarferry car ferry
    2. Fly from Haines Airport (HNS) to Chicago Midway International Airport (MDW)plane plane HNS - MDW
    12h 34m
    $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 14m
    $374–1,027

  8. 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 4m
    $300–1,148

  9. 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
    15h 46m
    $208–789

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

Calendar14Weekly Planes
Duration13h 15mAverage Duration
Ticket$231Cheapest Price
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Questions & Answers

Map of how to get from Skagway to Chicago.ExpandLaunch map view
  • Distance: 2,356.8 mi
  • Duration: 13h 6m

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

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

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