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How to get fromChicago Union Station to Winnipegby plane, bus (Greyhound, Flixbus), train (Amtrak), car, train, or bus

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There are 10 ways to get from Chicago Union Station to Winnipeg by plane, bus (Greyhound, Flixbus), train (Amtrak), car, 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. 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
    6h 2m
    $276–1,210

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

    cheapest
    1. Fly from Chicago Midway International Airport (MDW) to Winnipeg J. A. Richardson International Airport (YWG)plane plane MDW - YWG
    8h 13m
    $136–710

  3. Bus

    1. Take the bus from Chicago Bus Station to Milwaukee Intermodal Stationbus bus
    2. Take the bus from Milwaukee to Escanababus bus
    3. Take the bus from Escanaba, MI to Sault Ste. Marie, MIbus bus
    4. Take the bus from Sault Ste Marie to Thunder Baybus bus
    5. Take the bus from Thunder Bay to Winnipegbus bus
    33h 18m
    $201–490

  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
    $649–1,510

  5. Drive 1,382.3 km

    1. Drive from Chicago Union Station to Winnipegcar car 1,382.3 km
    14h 4m
    $273–394

  6. 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
    8h 29m
    $184–850

  7. 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 Winnipegcar car
    7h 39m
    $153–587

  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
    10h 1m
    $142–673

  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
    $556–1,160

  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
    $719–1,672

Chicago Union Station to Winnipeg by train and car

Calendar2Weekly Services
Duration46h 19mAverage Duration
Ticket$649Cheapest Price
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Questions & Answers

Map of how to get from Chicago Union Station to Winnipeg.ExpandLaunch map view
  • Distance: 1,173.7 km
  • Duration: 6h 2m

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

United Airlines, Delta, and Air Canada fly from Chicago O'Hare International Airport (ORD) to Winnipeg J. A. Richardson International Airport (YWG) every 4 hours. Alternatively, you can take a vehicle from Chicago Union Station to Winnipeg via Chicago Bus Station, Milwaukee Intermodal Station, Milwaukee, Escanaba, MI, Sault Ste. Marie, MI, Sault Ste Marie, and Thunder Bay in around 33h 18m.

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