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How to get fromChicago to Winnipegby plane, bus, car, train (Amtrak) or train

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There are 10 ways to get from Chicago to Winnipeg 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 Chicago O'Hare International Airport to Winnipeg J. A. Richardson International Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Winnipeg J. A. Richardson International Airport (YWG)plane plane ORD - YWG
    5h 55m
    $266–910

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

    cheapest
    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 Winnipegcar car
    7h 24m
    $138–527

  3. Bus, drive

    1. Take the bus from Chicago Bus Station to Kalamazoo Bus Stopbus bus
    2. Take the bus from Kalamazoo, MI to St. Ignace, MIbus bus
    3. Drive from St. Ignace, MI to Sault Ste Mariecar car
    4. Take the bus from Sault Ste Marie to Thunder Baybus bus
    5. Take the bus from Thunder Bay to Winnipegbus bus
    34h 16m
    $338–544

  4. Train via Detroit

    1. Take the train from Chicago Union Station to Detroittrain train
    2. Take the train from Windsor to Toronto Union Stationtrain train
    3. Take the train from Toronto Union Station to Winnipegtrain train
    46h 19m
    $316–576

  5. Drive 1,383.6 km

    1. Drive from Chicago to Winnipegcar car 1,383.6 km
    14h 5m
    $268–387

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

    1. Fly from Chicago Midway International Airport (MDW) to Winnipeg J. A. Richardson International Airport (YWG)plane plane MDW - YWG
    7h 13m
    $496–960

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

    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
    9h 5m
    $186–1,012

  8. Train to South Bend, fly to Winnipeg J. A. Richardson International Airport

    1. Take the train from Van Buren St. to South Bend Airporttrain train
    2. Fly from South Bend (SBN) to Winnipeg J. A. Richardson International Airport (YWG)plane plane SBN - YWG
    9h 25m
    $181–923

  9. Bus, train

    1. Take the bus from Chicago Bus Station to Detroit Bus Stationbus bus
    2. Take the bus from Detroit Bus Station to Torontobus bus
    3. Take the train from Toronto Union Station to Winnipegtrain train
    2d 1h
    $293–470

  10. Train

    1. Take the train from Chicago Union Station to Buffalo Depew Stationtrain train
    2. Take the train from Buffalo to Toronto Union Stationtrain train
    3. Take the train from Toronto Union Station to Winnipegtrain train
    2d 3h
    $307–629

Chicago to Winnipeg by train and car

Calendar2Weekly Services
Duration46h 19mAverage Duration
Ticket$316Cheapest Price
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Questions & Answers

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

United Airlines, Delta, and three other airlines fly from Chicago O'Hare International Airport (ORD) to Winnipeg J. A. Richardson International Airport (YWG) every 4 hours. Alternatively, you can take a train from Chicago Union Station to Winnipeg via Detroit, Windsor, and Toronto Union Station in around 46h 19m.

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