Rome2Rio

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

Find Transport to Chicago

See all options

There are 9 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 35m
    $184–857

  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 28m
    $79–407

  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
    $442–1,024

  4. Drive  860.9 mi

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

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

    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 46m
    $97–369

  6. 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 45m
    $95–416

  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
    9h 34m
    $136–669

  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 4h
    $391–776

  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 6h
    $476–1,121

Manitoba to Chicago by train and car

Calendar2Weekly Services
Duration2d 1hAverage Duration
Ticket$442Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Manitoba to Chicago.ExpandLaunch map view
  • Distance: 728.2 mi
  • Duration: 5h 35m

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

United Airlines and Delta 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 1h.

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