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How to get fromWinkler to Chicagoby car, plane, bus, or train

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There are 8 ways to get from Winkler to Chicago by car, plane, bus, 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 Winkler 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 15m
    $428–879

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

    cheapest
    1. Drive from Winkler to Grand Forks International Airport (GFK)car car
    2. Fly from Grand Forks International Airport (GFK) to Chicago O'Hare International Airport (ORD)plane plane GFK - ORD
    8h 18m
    $80–346

  3. Drive, bus

    1. Drive from Winkler to Southdale Mallcar car
    2. Take the bus from Southdale Mall to Thunder Baybus bus
    3. Take the bus from Thunder Bay to Sault Ste Mariebus bus
    4. Drive from Sault Ste Marie to St. Ignacecar car
    5. Take the bus from St. Ignace to East Lansingbus bus
    6. Take the bus from East Lansing Amtrak Station to Chicago Union Stationbus bus
    33h 28m

  4. Drive, train

    1. Drive from Winkler to Winnipegcar car
    2. Take the train from Winnipeg to Toronto Union Stationtrain train
    3. Take the train from Toronto Union Station to Windsortrain train
    4. Take the train from Detroit to Chicago Union Stationtrain train
    2d 3h
    $547–1,176

  5. Drive  837.1 mi

    1. Drive from Winkler to Chicagocar car 837.1 mi
    13h 29m
    $192–277

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

    1. Drive from Winkler to Fargo-Airport-FARcar car
    2. Fly from Hector International Airport (FAR) to Chicago O'Hare International Airport (ORD)plane plane FAR - ORD
    5h 46m
    $92–359

  7. Drive to Grand Forks International Airport, fly to Chicago Midway International Airport

    1. Drive from Winkler to Grand Forks International Airport (GFK)car car
    2. Fly from Grand Forks International Airport (GFK) to Chicago Midway International Airport (MDW)plane plane GFK - MDW
    8h 36m
    $100–446

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

    1. Drive from Winkler 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
    6h 44m
    $98–459

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

Calendar41Weekly Planes
Duration4h 59mAverage Duration
Ticket$58Cheapest Price
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Comparing Your Travel Options

Map of how to get from Winkler to Chicago.ExpandLaunch map view
  • Distance: 795.7 mi
  • Duration: 5h 15m

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

There is no direct connection from Winkler 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 take a vehicle from Winkler to Chicago Union Station via Southdale Mall, Thunder Bay, Sault Ste Marie, St. Ignace, East Lansing, and East Lansing Amtrak Station in around 33h 28m.

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