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

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There are 10 ways to get from Winnipeg to Illinois by plane, bus (Greyhound, Flixbus), train (Amtrak), car, bus, 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 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 42m
    $204–857

  2. Fly 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
    8h 18m
    $74–367

  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 30m
    $142–377

  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
    $474–1,069

  5. Drive 860.9 mi

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

  6. Fly to Dane County Regional Airport-Truax Field, drive

    1. Fly from Winnipeg J. A. Richardson International Airport (YWG) to Dane County Regional Airport-Truax Field (MSN)plane plane YWG - MSN
    2. Drive from Madison-Airport-MSN to Rockfordcar car
    7h 13m
    $115–572

  7. Fly to Peoria International Airport

    1. Fly from Winnipeg J. A. Richardson International Airport (YWG) to Peoria International Airport (PIA)plane plane YWG - PIA
    9h 45m
    $83–403

  8. Fly 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
    8h 47m
    $132–597

  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
    $428–846

  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
    $523–1,196

Winnipeg to Illinois by train and car

Calendar2Weekly Services
Duration2d 1hAverage Duration
Ticket$474Cheapest Price
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Questions & Answers

Map of how to get from Winnipeg to Illinois.ExpandLaunch map view
  • Distance: 728.5 mi
  • Duration: 5h 42m

What companies run services between Winnipeg, MB, Canada and Illinois, 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 30m.

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