Rome2Rio

How to get fromSaskatchewan to ChicagoBy car, or plane

Find Transport to Chicago

See all options

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 34m
    $99–437

  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 14m
    $119–527

  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 2m
    $234–957

  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 18m
    $244–807

  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
    12h 7m
    $214–957

  7. Fly Regina to Chicago Midway International Airport

    1. Fly from Regina (YQR) to Chicago Midway International Airport (MDW)plane plane YQR - MDW
    9h 1m
    $174–757

  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 56m
    $119–451

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

Calendar45Weekly Planes
Duration6h 5mAverage Duration
Ticket$78Cheapest Price
See schedules

Questions & Answers

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

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Where to next?

Trips from Saskatchewan

Trips to Chicago

Popular routes