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

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There are 7 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)planeYYC - ORD
    6h 54m
    $125–708

  2. 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
    35h 54m
    $145–357

  3. Drive 1,592.9 mi

    1. Drive from Calgary to Chicagocar1,592.9 mi
    27h 16m
    $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 55m
    $235–858

  5. Fly to General Mitchell International Airport, train

    1. Fly from Calgary International Airport (YYC) to General Mitchell International Airport (MKE)planeYYC - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain
    10h 49m
    $210–978

  6. Fly to South Bend, train

    1. Fly from Calgary International Airport (YYC) to South Bend (SBN)planeYYC - SBN
    2. Take the train from South Bend Airport to Van Buren St.train
    11h 26m
    $146–618

  7. 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
    $178–485

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

Calendar48Weekly Planes
Duration5h 38mAverage 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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