Rome2Rio

How to get fromBrandon to Chicagoby car or plane

Find Transport to Chicago

See all options

There are 6 ways to get from Brandon 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 Winnipeg J. A. Richardson International Airport, fly to Chicago O'Hare International Airport

    best
    1. Drive from Brandon to Winnipeg-Airport-YWGcar car
    2. Fly from Winnipeg J. A. Richardson International Airport (YWG) to Chicago O'Hare International Airport (ORD)plane plane YWG - ORD
    5h 38m
    $212–898

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

    cheapest
    1. Drive from Brandon to Minot International Airport (MOT)car car
    2. Fly from Minot International Airport (MOT) to Chicago O'Hare International Airport (ORD)plane plane MOT - ORD
    8h 12m
    $100–389

  3. Drive  970 mi

    1. Drive from Brandon to Chicagocar car 970 mi
    16h 13m
    $222–321

  4. Drive to Winnipeg J. A. Richardson International Airport, fly to Chicago Midway International Airport

    1. Drive from Brandon to Winnipeg-Airport-YWGcar car
    2. Fly from Winnipeg J. A. Richardson International Airport (YWG) to Chicago Midway International Airport (MDW)plane plane YWG - MDW
    7h 33m
    $107–448

  5. Drive to Minot International Airport, fly to Chicago Midway International Airport

    1. Drive from Brandon 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 17m
    $115–469

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

    1. Drive from Brandon to Bismarck-Airport-BIScar car
    2. Fly from Bismarck Municipal Airport (BIS) to Chicago O'Hare International Airport (ORD)plane plane BIS - ORD
    8h 5m
    $121–410

Winnipeg J. A. Richardson International Airport (YWG) to Chicago O'Hare International Airport (ORD) flights

Calendar41Weekly Planes
Duration4hAverage Duration
Ticket$60Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Brandon to Chicago.ExpandLaunch map view
  • Distance: 854.2 mi
  • Duration: 5h 38m

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

There is no direct connection from Brandon to Chicago. However, you can drive to Winnipeg-Airport-YWG airport, fly to Chicago O'Hare International Airport (ORD), walk to O'Hare, then take the subway to Jackson-Blue. Alternatively, you can drive from Brandon to Chicago in around 16h 13m.

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