There are 5 ways to get from Chicago to Winnipeg by plane, train, bus or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner.

Recommended option

Fly from Chicago O'Hare  •  5 h 38 min

  1. Fly from Chicago O'Hare (ORD) to Winnipeg (YWG) ORD - YWG

$205 - $488

Cheapest option

Train, bus  •  22 h 30 min

  1. Take the train from Chicago Union Station to St. Paul-Minneapolis Union Depot
  2. Take the bus from Minneapolis, MN to Grand Forks, ND 927
  3. Take the bus from Grand Forks, ND to Winnipeg Airport

$170 - $333

3 alternative options

Fly from Chicago Midway  •  6 h 56 min

  1. Fly from Chicago Midway (MDW) to Winnipeg (YWG) MDW - YWG

$215 - $477

Bus  •  25 h 5 min

  1. Take the bus from Chicago, Il to Milwaukee, Wi
  2. Take the bus from Milwaukee to Minneapolis, MN 966 / ...
  3. Take the bus from Minneapolis, MN to Grand Forks, ND 927
  4. Take the bus from Grand Forks, ND to Winnipeg Airport

$179 - $278

Drive  •  14 h 36 min

  1. Drive from Chicago to Winnipeg 867.7 miles

$110 - $170

Questions & Answers

No, there is no direct bus from Chicago to Winnipeg. However, there are services departing from Chicago, Il and arriving at Eastbound Broadway at Osborne via Milwaukee, Minneapolis, MN, Grand Forks, ND and Southbound Wellington at Greyhound Terminal. The journey, including transfers, takes approximately 25 h 5 min.

More details

The distance between Chicago and Winnipeg is 721 miles. The road distance is 867.7 miles.

Get driving directions

The best way to get from Chicago to Winnipeg without a car is to train and bus which takes 22 h 30 min and costs .

More details

It takes approximately 5 h 38 min to get from Chicago to Winnipeg, including transfers.

More details

Chicago to Winnipeg bus services, operated by Greyhound USA, depart from Chicago, Il station.

More details

The best way to get from Chicago to Winnipeg is to fly which takes 5 h 38 min and costs . Alternatively, you can bus, which costs and takes 25 h 5 min.

Mode details

The quickest flight from Chicago O'Hare Airport to Winnipeg Airport is the direct flight which takes 2 h 15 min.

Search flights

Chicago to Winnipeg bus services, operated by Jefferson Lines, arrive at Winnipeg Airport station.

More details

Yes, the driving distance between Chicago to Winnipeg is 868 miles. It takes approximately 14 h 36 min to drive from Chicago to Winnipeg.

Get driving directions

Delta, United Airlines and Air Canada offer flights from Chicago O'Hare Airport to Winnipeg Airport.

Search flights

Map of how to get from Chicago to Winnipeg.
Launch map view
  • Distance: 721.2 miles
  • Duration: 5 h 38 min

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

United Airlines, Air Canada and Delta fly from Chicago to Winnipeg every 4 hours. Alternatively, you can take a bus from Chicago to Winnipeg via Milwaukee, Wi, Milwaukee, Minneapolis, MN, Grand Forks, ND, Winnipeg Airport, and Southbound Wellington at Greyhound Terminal in around 25 h 5 min.

Airlines
Delta
Website
delta.com
Flights from Chicago O'Hare to Winnipeg via Minneapolis
Ave. Duration
5 h 22 min
When
Monday to Friday
Estimated price
$300 - $1,200
Flights from Chicago Midway to Winnipeg via Minneapolis
Ave. Duration
4 h 44 min
When
Every day
Estimated price
$220 - $850
Flights from Chicago Midway to Winnipeg via Detroit, Minneapolis
Ave. Duration
6 h 51 min
When
Every day
Estimated price
$220 - $850
United Airlines
Website
united.com
Flights from Chicago O'Hare to Winnipeg
Ave. Duration
2 h 22 min
When
Every day
Estimated price
$240 - $1,200
Flights from Chicago O'Hare to Winnipeg via Toronto
Ave. Duration
5 h 18 min
When
Every day
Estimated price
$250 - $1,300
Air Canada
Website
aircanada.com
Flights from Chicago O'Hare to Winnipeg
Ave. Duration
2 h 22 min
When
Every day
Estimated price
$240 - $1,200
Flights from Chicago O'Hare to Winnipeg via Toronto
Ave. Duration
5 h 15 min
When
Every day
Estimated price
$250 - $1,300
Train operators
Amtrak

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Chicago Union Station to St. Paul-Minneapolis Union Depot
Ave. Duration
7 h 48 min
Frequency
3 times a day
Estimated price
$65 - $180
Website
amtrak.com
Coach Seat
$65 - $100
Flexi Coach Seat
$110 - $170
Business Coach Seat
$120 - $180
Room
$280 - $400
Bus operators
Jefferson Lines
Phone
800-451-5333
Email
info@jeffersonlines.com
Website
jeffersonlines.com
Bus from Minneapolis, MN to Grand Forks, ND
Ave. Duration
7 h 45 min
Frequency
Every 3 hours
Estimated price
$60 - $90
Book at
jeffersonlines.com
Bus from Grand Forks, ND to Winnipeg Airport
Ave. Duration
3 h 35 min
Frequency
5 times a week
Estimated price
$30 - $50
Book at
jeffersonlines.com
Bus from Milwaukee to Minneapolis, MN
Ave. Duration
8 h 10 min
Frequency
Hourly
Estimated price
$70 - $100
Book at
jeffersonlines.com
Greyhound USA

Greyhound is a leading bus company based in Dallas, Texas, serving over 3800 destinations across North America, Mexico and Canada. Greyhound carries around 18 million passengers a year who travel 5.4 billion miles (8.6 billion km) a year on their fleet of around 1700 vehicles. For travel flexibility, you can board or get off a Greyhound bus at official Greyhound stations, partner stations and curbside stops. There are around 230 Greyhound stations across the US where you can both catch your bus and buy tickets, that are also available on the official website and via the mobile app.

Rome2rio's guide to Greyhound USA
Contact Details
Phone
+1 214-849-8100/1-800-231-2222
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from Chicago, Il to Milwaukee, Wi
Ave. Duration
2 h 20 min
Frequency
Every 20 minutes
Estimated price
$15 - $35
Website
greyhound.com
Economy
$15 - $23
Flexible
$28 - $35

Want to know more about travelling around Canada

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.

More Questions & Answers

There are 96+ hotels available in Winnipeg. Prices start at $59 USD per night.

More details

The best way to get from Chicago to Chicago O'Hare Airport is to subway which takes 42 min and costs .

More details