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How to get fromCalgary to Chicago, ILby plane, bus, car or train

Find Transport to Chicago, IL

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There are 5 ways to get from Calgary to Chicago, IL 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)planeYYC - ORD
    7h 1m
    $115–658

  2. Bus, drive, train via Saint Paul

    1. Take the bus from Calgary to Lethbridgebus
    2. Drive from Lethbridge to Port of Sweet Grasscar
    3. Take the bus from Port of Sweet Grass to Shelby Transit Centerbus
    4. Take the train from Shelby Amtrak Station to St. Paul-Minneapolistrain
    5. Take the bus from Saint Paul Union Depot to Chicago Bus Stationbus
    35h 54m
    $168–398

  3. Drive 1,592.1 mi

    1. Drive from Calgary to Chicago, ILcar1,592.1 mi
    27h 14m
    $365–527

  4. Fly to Chicago Midway International Airport

    1. Fly from Calgary International Airport (YYC) to Chicago Midway International Airport (MDW)planeYYC - MDW
    8h 36m
    $235–858

  5. Bus, drive, train

    1. Take the bus from Calgary to Lethbridgebus
    2. Drive from Southgate Station to Port of Sweet Grasscar
    3. Take the bus from Port of Sweet Grass to Shelby Transit Centerbus
    4. Take the train from Shelby Amtrak Station to Chicago Union Stationtrain
    36h 3m
    $175–470

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

Calendar61Weekly Planes
Duration5h 47mAverage Duration
Ticket$74Cheapest Price
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Questions & Answers

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

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

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