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How to get fromBrandon to Chicagoby car, plane, or train

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There are 7 ways to get from Brandon to Chicago by car, plane, or train

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 53m
    $89–374

  2. Drive  970 mi

    1. Drive from Brandon to Chicagocar car 970 mi
    16h 13m
    $200–289

  3. 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
    8h 8m
    $114–524

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

    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
    9h 47m
    $96–374

  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
    9h 23m
    $121–514

  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
    7h 59m
    $110–391

  7. Drive to Winnipeg J. A. Richardson International Airport, fly to General Mitchell International Airport, train

    1. Drive from Brandon to Winnipeg-Airport-YWGcar car
    2. Fly from Winnipeg J. A. Richardson International Airport (YWG) to General Mitchell International Airport (MKE)plane plane YWG - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    9h 56m
    $184–778

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

Calendar33Weekly Planes
Duration4h 53mAverage Duration
Ticket$60Cheapest Price
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Comparing Your Travel Options

Map of how to get from Brandon to Chicago.ExpandLaunch map view
  • Distance: 854.2 mi
  • Duration: 5h 53m

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.

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