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

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There are 10 ways to get from Winnipeg to Chicago 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 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 41m
    $204–857

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

    cheapest
    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 46m
    $125–617

  3. Bus

    1. Take the bus from Winnipeg to Thunder Baybus bus
    2. Take the bus from Thunder Bay to Sault Ste Mariebus bus
    3. Take the bus from Sault Ste. Marie, MI to Escanaba, MIbus bus
    4. Take the bus from Escanaba to Milwaukeebus bus
    5. Take the bus from Milwaukee Intermodal Station to Chicago Bus Stationbus bus
    32h 23m
    $141–350

  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
    $473–1,068

  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
    8h 18m
    $324–807

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

    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 26m
    $142–577

  8. 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
    9h 11m
    $132–621

  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
    $397–815

  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
    $522–1,195

Winnipeg to Chicago by train and car

Calendar2Weekly Services
Duration2d 1hAverage Duration
Ticket$473Cheapest Price
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Questions & Answers

Map of how to get from Winnipeg to Chicago.ExpandLaunch map view
  • Distance: 728.5 mi
  • Duration: 5h 41m

What companies run services between Winnipeg, MB, 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 bus from Winnipeg to Chicago Bus Station via Thunder Bay, Sault Ste Marie, Sault Ste. Marie, MI, Escanaba, Milwaukee, and Milwaukee Intermodal Station in around 32h 23m.

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