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How to get fromSaskatchewan to Chicagoby plane, car, or train

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There are 8 ways to get from Saskatchewan to Chicago by plane, 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 Regina to Chicago O'Hare International Airport

    best
    1. Fly from Regina (YQR) to Chicago O'Hare International Airport (ORD)plane plane YQR - ORD
    7h 51m
    $114–557

  2. Fly Saskatoon John G. Diefenbaker International Airport to Chicago O'Hare International Airport

    cheapest
    1. Fly from Saskatoon John G. Diefenbaker International Airport (YXE) to Chicago O'Hare International Airport (ORD)plane plane YXE - ORD
    8h 25m
    $104–487

  3. Drive  1,307.6 mi

    1. Drive from Saskatoon to Chicagocar car 1,307.6 mi
    22h 33m
    $300–433

  4. Drive to Minot International Airport, fly to Chicago Midway International Airport

    1. Drive from Estevan to Minot International Airport (MOT)car car
    2. Fly from Minot International Airport (MOT) to Chicago Midway International Airport (MDW)plane plane MOT - MDW
    8h 56m
    $104–444

  5. Fly Regina to Chicago Midway International Airport

    1. Fly from Regina (YQR) to Chicago Midway International Airport (MDW)plane plane YQR - MDW
    7h 52m
    $144–707

  6. Fly Saskatoon John G. Diefenbaker International Airport to Chicago Midway International Airport

    1. Fly from Saskatoon John G. Diefenbaker International Airport (YXE) to Chicago Midway International Airport (MDW)plane plane YXE - MDW
    11h 17m
    $144–657

  7. Drive to Bismarck Municipal Airport, fly to Chicago O'Hare International Airport

    1. Drive from Estevan to Bismarck-Airport-BIScar car
    2. Fly from Bismarck Municipal Airport (BIS) to Chicago O'Hare International Airport (ORD)plane plane BIS - ORD
    7h 30m
    $109–391

  8. Fly Regina to General Mitchell International Airport, train

    1. Fly from Regina (YQR) to General Mitchell International Airport (MKE)plane plane YQR - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    10h
    $237–1,076

Regina (YQR) to Chicago O'Hare International Airport (ORD) flights

Calendar47Weekly Planes
Duration6h 57mAverage Duration
Ticket$117Cheapest Price
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Comparing Your Travel Options

Map of how to get from Saskatchewan to Chicago.ExpandLaunch map view
  • Distance: 1,008.9 mi
  • Duration: 7h 51m

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

WestJet, Delta, and two other airlines fly from Regina (YQR) to Chicago O'Hare International Airport (ORD) every 4 hours.

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