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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
    7h 21m
    $94–387

  2. Drive 1,307.6 mi

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

  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 10m
    $119–517

  4. 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 11m
    $234–907

  5. 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
    8h 21m
    $274–857

  6. Fly Regina to Chicago Midway International Airport

    1. Fly from Regina (YQR) to Chicago Midway International Airport (MDW)plane plane YQR - MDW
    8h 25m
    $174–757

  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
    10h 47m
    $224–907

  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 34m
    $114–401

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

Calendar45Weekly Planes
Duration5h 44mAverage Duration
Ticket$71Cheapest Price
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Questions & Answers

Map of how to get from Saskatchewan to Chicago.ExpandLaunch map view
  • Distance: 998.3 mi
  • Duration: 7h 21m

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.

Airlines

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