Rome2Rio

How to get fromSaskatchewan to Chicagoby plane or car

Find Transport to Chicago

See all options

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

    best
    1. Fly from Saskatoon John G. Diefenbaker International Airport (YXE) to Chicago O'Hare International Airport (ORD)plane plane YXE - ORD
    6h 59m
    $255–821

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

    cheapest
    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 13m
    $79–337

  3. Drive 1,305.9 mi

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

  4. 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
    6h 4m
    $255–1,621

  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 34m
    $124–587

  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
    9h 5m
    $124–594

  7. 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 14m
    $124–857

  8. Fly Regina to Chicago Midway International Airport

    1. Fly from Regina (YQR) to Chicago Midway International Airport (MDW)plane plane YQR - MDW
    8h 45m
    $144–707

Saskatoon John G. Diefenbaker International Airport (YXE) to Chicago O'Hare International Airport (ORD) flights

Calendar38Weekly Planes
Duration6h 56mAverage Duration
Ticket$125Cheapest Price
See schedules

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.

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