Rome2Rio

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

Find Transport to Chicago

See all options
QR code to download the Rome2Rio app

Download the Rome2Rio travel app

Scan QR code with your phone to download the app

Download on the App StoreGet it on Google Play

There are 9 ways to get from Winnipeg to Chicago by plane, bus, car, train (Amtrak), 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 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 45m
    $64–337

  2. Bus, drive

    1. Take the bus from Winnipeg to Thunder Baybus bus
    2. Take the bus from Thunder Bay to Sault Ste Mariebus bus
    3. Drive from Sault Ste Marie to St. Ignacecar car
    4. Take the bus from St. Ignace to East Lansingbus bus
    5. Take the bus from East Lansing Amtrak Station to Chicago Union Stationbus bus
    32h 1m

  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 2h
    $523–1,105

  4. Drive  860.9 mi

    1. Drive from Winnipeg to Chicagocar car 860.9 mi
    14h 7m
    $165–238

  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 24m
    $94–355

  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
    7h 59m
    $89–487

  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 4m
    $96–459

  8. 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 5h
    $397–793

  9. 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
    $637–1,273

Winnipeg to Chicago by train and car

Calendar2Weekly Services
Duration2d 2hAverage Duration
Ticket$523Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Winnipeg to Chicago.ExpandLaunch map view
  • Distance: 728.7 mi
  • Duration: 5h 45m

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) 5 times a day. Alternatively, you can take a train from Winnipeg to Chicago Union Station via Toronto Union Station, Windsor, and Detroit in around 2d 2h.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

Booking & Getting There