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How to get fromSaskatchewan to Chicagoby plane or car

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

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
    9h 2m
    $124–807

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

    cheapest
    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 53m
    $109–391

  3. Drive 1,307.7 mi

    1. Drive from Saskatoon to Chicagocar car 1,307.7 mi
    22h 38m
    $300–433

  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 18m
    $284–957

  5. 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
    $114–517

  6. 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 14m
    $114–504

  7. Fly Regina to Chicago Midway International Airport

    1. Fly from Regina (YQR) to Chicago Midway International Airport (MDW)plane plane YQR - MDW
    8h 36m
    $124–657

  8. 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
    13h 24m
    $244–1,007

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

Calendar35Weekly Planes
Duration6h 48mAverage Duration
Ticket$120Cheapest Price
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Questions & Answers

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

Air Canada, WestJet, and three other airlines fly from Regina (YQR) to Chicago O'Hare International Airport (ORD) 5 times a day.

Airlines

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