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How to get fromWinnipeg to Chicago Midway Airport (MDW)by plane, train, bus, car, or train (Amtrak)

Find Transport to Chicago Midway Airport (MDW)

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There are 8 ways to get from Winnipeg to Chicago Midway Airport (MDW) by plane, train, bus, car, or train (Amtrak)

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
    6h 11m
    $206–862

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

    cheapest
    1. Fly from Winnipeg J. A. Richardson International Airport (YWG) to Chicago Midway International Airport (MDW)plane plane YWG - MDW
    7h 37m
    $72–392

  3. 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 Chicagobus bus
    2d 7h
    $415–827

  4. Drive 863.7 mi

    1. Drive from Winnipeg to Chicago Midway Airport (MDW)car car 863.7 mi
    14h 17m
    $198–286

  5. 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 55m
    $144–632

  6. Fly Winnipeg J. A. Richardson International Airport to General Mitchell International Airport, bus

    1. Fly from Winnipeg J. A. Richardson International Airport (YWG) to General Mitchell International Airport (MKE)plane plane YWG - MKE
    2. Take the bus from Mitchell Airport to O'Hare International Airport - Terminal 2 Departuresbus bus
    9h 35m
    $141–601

  7. 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
    10h 26m
    $127–622

  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 7h
    $520–1,207

Winnipeg to Chicago Midway Airport (MDW) by train, bus, and subway

Calendar2Weekly Services
Duration2d 7hAverage Duration
Ticket$415Cheapest Price
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Questions & Answers

Map of how to get from Winnipeg to Chicago Midway Airport (MDW).ExpandLaunch map view
  • Distance: 739.1 mi
  • Duration: 6h 11m

What companies run services between Winnipeg, MB, Canada and Chicago Midway Airport (MDW), 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 Midway via Toronto Union Station, Buffalo Depew Station, Chicago Union Station, Jackson & Clinton, Jackson & Wabash, and Adams/Wabash in around 2d 7h.

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