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

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There are 10 ways to get from Manitoba to Chicago by plane, 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 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 49m
    $264–707

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

    cheapest
    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 51m
    $87–329

  3. 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
    $258–484

  4. Drive 860.9 mi

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

  5. 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 46m
    $105–496

  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 49m
    $244–807

  7. Fly Winnipeg J. A. Richardson International Airport to General Mitchell International Airport, train

    1. Fly from Winnipeg J. A. Richardson International Airport (YWG) to General Mitchell International Airport (MKE)plane plane YWG - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    10h 10m
    $167–871

  8. Fly Winnipeg J. A. Richardson International Airport to South Bend, train

    1. Fly from Winnipeg J. A. Richardson International Airport (YWG) to South Bend (SBN)plane plane YWG - SBN
    2. Take the train from South Bend Airport to Van Buren St.train train
    9h 36m
    $135–717

  9. 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
    $212–351

  10. 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
    $310–611

Manitoba to Chicago by train and car

Calendar2Weekly Services
Duration2d 1hAverage Duration
Ticket$258Cheapest Price
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Questions & Answers

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

United Airlines, Delta, and Air Canada fly from Winnipeg J. A. Richardson International Airport (YWG) to Chicago O'Hare International Airport (ORD) every 4 hours. 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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