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How to get fromSaskatchewan to Chicagoby car or plane

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There are 8 ways to get from Saskatchewan to Chicago by car or plane

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Drive to Ring Rock Ranch Airport, fly to Chicago O'Hare International Airport

    best
    1. Drive from Estevan to Ring Rock Ranch Airport (XWA)car car
    2. Fly from Ring Rock Ranch Airport (XWA) to Chicago O'Hare International Airport (ORD)plane plane XWA - ORD
    8h 17m
    $84–357

  2. Drive 1,305.9 mi

    1. Drive from Saskatoon to Chicagocar car 1,305.9 mi
    22h 42m
    $299–432

  3. Drive to Ring Rock Ranch Airport, fly to Chicago Midway International Airport

    1. Drive from Estevan to Ring Rock Ranch Airport (XWA)car car
    2. Fly from Ring Rock Ranch Airport (XWA) to Chicago Midway International Airport (MDW)plane plane XWA - MDW
    8h 33m
    $124–587

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

    1. Fly from Saskatoon John G. Diefenbaker International Airport (YXE) to Chicago O'Hare International Airport (ORD)plane plane YXE - ORD
    9h 13m
    $244–807

  5. Fly Regina to Chicago O'Hare International Airport

    1. Fly from Regina (YQR) to Chicago O'Hare International Airport (ORD)plane plane YQR - ORD
    8h 59m
    $174–807

  6. Fly Regina to Chicago Midway International Airport

    1. Fly from Regina (YQR) to Chicago Midway International Airport (MDW)plane plane YQR - MDW
    9h 10m
    $134–707

  7. 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
    8h 16m
    $324–1,407

  8. 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 54m
    $104–371

Ring Rock Ranch Airport (XWA) to Chicago O'Hare International Airport (ORD) flights

Calendar29Weekly Planes
Duration6h 7mAverage Duration
Ticket$60Cheapest Price
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Questions & Answers

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

WestJet, Air Canada, and two other airlines fly from Saskatoon John G. Diefenbaker International Airport (YXE) to Chicago O'Hare International Airport (ORD) 5 times a day.

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