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How to get fromCalgary to Chicagoby plane, bus, car, or train

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

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 to Chicago O'Hare International Airport

    best
    1. Fly from Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD)plane plane YYC - ORD
    6h 21m
    $152–846

  2. Fly to Chicago Midway International Airport

    cheapest
    1. Fly from Calgary International Airport (YYC) to Chicago Midway International Airport (MDW)plane plane YYC - MDW
    8h 25m
    $106–481

  3. Bus, drive, train

    1. Take the bus from Calgary Flix bus to Lethbridgebus bus
    2. Drive from Lethbridge to Port of Sweet Grasscar car
    3. Take the bus from Port of Sweet Grass to Shelby Transit Centerbus bus
    4. Take the train from Shelby Amtrak Station to Chicago Union Stationtrain train
    35h 17m
    $385–902

  4. Drive  1,592.8 mi

    1. Drive from Calgary to Chicagocar car 1,592.8 mi
    27h 23m
    $365–527

  5. Fly to South Bend, train

    1. Fly from Calgary International Airport (YYC) to South Bend (SBN)plane plane YYC - SBN
    2. Take the train from South Bend Airport to Van Buren St.train train
    10h 21m
    $177–758

Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD) flights

Calendar67Weekly Planes
Duration5h 42mAverage Duration
Ticket$81Cheapest Price
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Comparing Your Travel Options

Map of how to get from Calgary to Chicago.ExpandLaunch map view
  • Distance: 1,409.7 mi
  • Duration: 6h 21m

What companies run services between Calgary, AB, Canada and Chicago, IL, USA?

American Airlines, United Airlines, and three other airlines fly from Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD) every 3 hours.

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