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How to get fromWasilla to Chicagoby train, plane or car

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There are 5 ways to get from Wasilla to Chicago by train, plane, or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Train, fly to Chicago O'Hare International Airport

    best
    1. Take the train from Wasilla to Anchoragetrain train
    2. Fly from Anchorage International Airport (ANC) to Chicago O'Hare International Airport (ORD)plane plane ANC - ORD
    9h 55m
    $363–1,437

  2. Drive 3,531 mi

    1. Drive from Wasilla to Chicagocar car 3,531 mi
    2d 17h
    $645–931

  3. Train, fly to Chicago Midway International Airport

    1. Take the train from Wasilla to Anchoragetrain train
    2. Fly from Anchorage International Airport (ANC) to Chicago Midway International Airport (MDW)plane plane ANC - MDW
    12h 14m
    $543–2,137

  4. Train, fly to General Mitchell International Airport

    1. Take the train from Wasilla to Anchoragetrain train
    2. Fly from Anchorage International Airport (ANC) to General Mitchell International Airport (MKE)plane plane ANC - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    14h 27m
    $885–3,552

  5. Train, fly to South Bend

    1. Take the train from Wasilla to Anchoragetrain train
    2. Fly from Anchorage International Airport (ANC) to South Bend (SBN)plane plane ANC - SBN
    3. Take the train from South Bend Airport to Van Buren St.train train
    15h 14m
    $624–2,447

Anchorage International Airport (ANC) to Chicago O'Hare International Airport (ORD) flights

Calendar44Weekly Planes
Duration8h 31mAverage Duration
Ticket$306Cheapest Price
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Questions & Answers

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

There is no direct connection from Wasilla to Chicago. However, you can take the train to Anchorage, walk to Downtown Transit Center, take the bus to Airport South Terminal, walk to Anchorage International Airport (ANC) airport, fly to Chicago O'Hare International Airport (ORD), walk to O'Hare, then take the subway to Jackson-Blue. Alternatively, you can drive from Wasilla to Chicago in around 2d 17h.

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