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

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There are 9 ways to get from Winkler to Chicago by car, plane, train, or bus

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 1m
    $188–879

  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
    6h 58m
    $80–346

  3. Drive, train via Detroit

    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
    $447–1,056

  4. Drive  837.1 mi

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

  5. 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

  6. 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 45m
    $95–426

  7. 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 55m
    $88–429

  8. Drive, train, bus

    1. Drive from Winkler to Northbound Pembina at De La Diguecar car
    2. Take the train from Winnipeg to Toronto Union Stationtrain train
    3. Take the bus from Toronto to Detroit Bus Stationbus bus
    4. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus
    2d 7h
    $404–802

  9. Drive, train

    1. Drive from Winkler to Northbound Pembina at De La Diguecar car
    2. Take the train from Winnipeg to Toronto Union Stationtrain train
    3. Take the train from Toronto Union Station to Buffalotrain train
    4. Take the train from Buffalo Depew Station to Chicago Union Stationtrain train
    2d 9h
    $489–1,157

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

Calendar35Weekly Planes
Duration3h 37mAverage Duration
Ticket$57Cheapest 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 1m

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 Winnipeg, Toronto Union Station, Windsor, and Detroit in around 2d 3h.

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