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How to get fromChicago to Brandonby plane, car, or train

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There are 9 ways to get from Chicago to Brandon by plane, car, 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. Fly Chicago O'Hare International Airport to Winnipeg J. A. Richardson International Airport, drive

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Winnipeg J. A. Richardson International Airport (YWG)plane plane ORD - YWG
    2. Drive from Winnipeg-Airport-YWG to Brandoncar car
    7h 47m
    $284–1,272

  2. Fly Chicago O'Hare International Airport to Minot International Airport, drive

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Minot International Airport (MOT)plane plane ORD - MOT
    2. Drive from Minot International Airport (MOT) to Brandoncar car
    9h 52m
    $144–577

  3. Drive  1,560.1 km

    1. Drive from Chicago to Brandoncar car 1,560.1 km
    16h 13m
    $314–454

  4. Fly Chicago Midway International Airport to Winnipeg J. A. Richardson International Airport, drive

    1. Fly from Chicago Midway International Airport (MDW) to Winnipeg J. A. Richardson International Airport (YWG)plane plane MDW - YWG
    2. Drive from Winnipeg-Airport-YWG to Brandoncar car
    8h 52m
    $174–822

  5. Fly Chicago Midway International Airport to Minot International Airport, drive

    1. Fly from Chicago Midway International Airport (MDW) to Minot International Airport (MOT)plane plane MDW - MOT
    2. Drive from Minot International Airport (MOT) to Brandoncar car
    9h 14m
    $184–837

  6. Fly Chicago O'Hare International Airport to Bismarck Municipal Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Bismarck Municipal Airport (BIS)plane plane ORD - BIS
    2. Drive from Bismarck-Airport-BIS to Brandoncar car
    9h 8m
    $169–597

  7. Train to General Mitchell International Airport, fly to Winnipeg J. A. Richardson International Airport, drive

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Winnipeg J. A. Richardson International Airport (YWG)plane plane MKE - YWG
    3. Drive from Winnipeg-Airport-YWG to Brandoncar car
    10h 37m
    $249–987

  8. Fly Chicago Midway International Airport to Grand Forks International Airport, drive

    1. Fly from Chicago Midway International Airport (MDW) to Grand Forks International Airport (GFK)plane plane MDW - GFK
    2. Drive from Grand Forks International Airport (GFK) to Brandoncar car
    9h 52m
    $204–827

  9. Fly Chicago O'Hare International Airport to Hector International Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Hector International Airport (FAR)plane plane ORD - FAR
    2. Drive from Fargo-Airport-FAR to Brandoncar car
    9h 32m
    $179–607

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

Calendar41Weekly Planes
Duration4h 13mAverage Duration
Ticket$88Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Brandon.ExpandLaunch map view
  • Distance: 1,374.5 km
  • Duration: 7h 47m

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

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

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