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

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There are 6 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 36m
    $217–839

  2. Fly to South Bend, train

    cheapest
    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 49m
    $198–799

  3. Bus, drive, train

    1. Take the bus from Calgary - Deerfoot Inn & Casino* to Lethbridge - U of Lbus bus
    2. Drive from Lethbridge - U of L 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
    34h 47m

  4. Drive 1,592.7 mi

    1. Drive from Calgary to Chicagocar car 1,592.7 mi
    27h 23m
    $365–527

  5. Fly to Chicago Midway International Airport

    1. Fly from Calgary International Airport (YYC) to Chicago Midway International Airport (MDW)plane plane YYC - MDW
    8h 21m
    $287–939

  6. Fly to General Mitchell International Airport, train

    1. Fly from Calgary International Airport (YYC) to General Mitchell International Airport (MKE)plane plane YYC - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    11h 9m
    $801–1,403

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

Calendar86Weekly Planes
Duration5h 31mAverage Duration
Ticket$90Cheapest Price
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Questions & Answers

Map of how to get from Calgary to Chicago.ExpandLaunch map view
  • Distance: 1,410.2 mi
  • Duration: 6h 36m

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

WestJet, American Airlines, and three other airlines fly from Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD) every 2 hours.

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