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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
    2. Fly from Anchorage International Airport (ANC) to Chicago O'Hare International Airport (ORD)planeANC - ORD
    9h 50m
    $413–1,637

  2. Drive 3,532.8 mi

    1. Drive from Wasilla to Chicagocar3,532.8 mi
    2d 16h
    $645–932

  3. Train, fly to Chicago Midway International Airport

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

  4. Train, fly to South Bend

    1. Take the train from Wasilla to Anchoragetrain
    2. Fly from Anchorage International Airport (ANC) to South Bend (SBN)planeANC - SBN
    3. Take the train from South Bend Airport to Van Buren St.train
    14h 34m
    $624–2,547

  5. Train, fly to General Mitchell International Airport

    1. Take the train from Wasilla to Anchoragetrain
    2. Fly from Anchorage International Airport (ANC) to General Mitchell International Airport (MKE)planeANC - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain
    14h
    $887–3,657

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

Calendar80Weekly Planes
Duration9hAverage Duration
Ticket$350Cheapest 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 16h.

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