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How to get fromWinnipeg to Chicagoby plane, bus, car, train (Amtrak) or train

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There are 8 ways to get from Winnipeg to Chicago by plane, bus, car, train (Amtrak), 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 Winnipeg J. A. Richardson International Airport to Chicago O'Hare International Airport

    best
    1. Fly from Winnipeg J. A. Richardson International Airport (YWG) to Chicago O'Hare International Airport (ORD)plane plane YWG - ORD
    5h 34m
    $194–657

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

    cheapest
    1. Drive from Winnipeg to Fargo-Airport-FARcar car
    2. Fly from Hector International Airport (FAR) to Chicago O'Hare International Airport (ORD)plane plane FAR - ORD
    6h 22m
    $97–347

  3. Bus, drive

    1. Take the bus from Winnipeg to Thunder Baybus bus
    2. Take the bus from Thunder Bay to Sault Ste Mariebus bus
    3. Drive from Sault Ste Marie to St. Ignace, MIcar car
    4. Take the bus from St. Ignace, MI to Kalamazoo, MIbus bus
    5. Take the bus from Kalamazoo Bus Stop to Chicago Bus Stationbus bus
    33h 46m
    $254–392

  4. Train via Detroit

    1. Take the train from Winnipeg to Toronto Union Stationtrain train
    2. Take the train from Toronto Union Station to Windsortrain train
    3. Take the train from Detroit to Chicago Union Stationtrain train
    2d 1h
    $224–395

  5. Drive 860.9 mi

    1. Drive from Winnipeg to Chicagocar car 860.9 mi
    14h 7m
    $197–285

  6. Fly Winnipeg J. A. Richardson International Airport to Chicago Midway International Airport

    1. Fly from Winnipeg J. A. Richardson International Airport (YWG) to Chicago Midway International Airport (MDW)plane plane YWG - MDW
    9h 28m
    $364–707

  7. Train, bus

    1. Take the train from Winnipeg to Toronto Union Stationtrain train
    2. Take the bus from Toronto to Detroit Bus Stationbus bus
    3. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus
    2d 4h
    $218–337

  8. Train

    1. Take the train from Winnipeg to Toronto Union Stationtrain train
    2. Take the train from Toronto Union Station to Buffalotrain train
    3. Take the train from Buffalo Depew Station to Chicago Union Stationtrain train
    2d 6h
    $226–482

Winnipeg to Chicago by train and car

Calendar2Weekly Services
Duration2d 1hAverage Duration
Ticket$224Cheapest Price
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Questions & Answers

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

United Airlines, Delta, and two other airlines fly from Winnipeg J. A. Richardson International Airport (YWG) to Chicago O'Hare International Airport (ORD) 3 times a day. Alternatively, you can take a train from Winnipeg to Chicago Union Station via Toronto Union Station, Windsor, and Detroit in around 2d 1h.

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