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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)plane plane YYC - ORD
    7h 3m
    $95–608

  2. Bus, drive, train

    1. Take the bus from Calgary to Lethbridgebus bus
    2. Drive from Southgate Station 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 40m
    $424–953

  3. Drive 1,592.1 mi

    1. Drive from Calgary to Chicago, ILcar car 1,592.1 mi
    27h 26m
    $365–527

  4. Fly to Chicago Midway International Airport

    1. Fly from Calgary International Airport (YYC) to Chicago Midway International Airport (MDW)plane plane YYC - MDW
    9h 25m
    $265–658

  5. Bus, drive, train via Saint Paul

    1. Take the bus from Calgary 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 St. Paul-Minneapolistrain train
    5. Take the bus from Saint Paul Union Depot to Chicago Bus Stationbus bus
    35h 45m
    $362–841

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

Calendar39Weekly Planes
Duration5h 26mAverage Duration
Ticket$75Cheapest 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 4 hours.

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