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 30 min

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

$205 - $488

Cheapest option

Train, bus  •  22 h 33 min

  1. Take the train from Chicago Union Station Amtrak to St. Paul-Minneapolis Union Depot Amtrak
  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 51 min

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

$215 - $477

Bus  •  24 h 24 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

$178 - $277

Drive  •  14 h 36 min

  1. Drive from Chicago to Winnipeg 867.7 miles

$110 - $170

Questions & Answers

The cheapest way to get from Chicago to Winnipeg is to drive which costs $110 - $170 and takes 14 h 36 min.

More details

The quickest way to get from Chicago to Winnipeg is to fly which costs $200 - $490 and takes 5 h 30 min.

More details

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

Get driving directions

It takes approximately 5 h 30 min to get from Chicago to Winnipeg, including transfers.

More details

No, there is no direct bus from Chicago to Winnipeg. However, there are services departing from Chicago, Il and arriving at Southbound Vaughan at Portage North via Milwaukee, Minneapolis, MN, Grand Forks, ND and Southbound Wellington at Greyhound Terminal. The journey, including transfers, takes approximately 24 h 24 min.

More details

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

United Airlines, Delta and Air Canada 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 24 h 24 min.

Airlines
Delta
Website
delta.com
Flights from Chicago O'Hare to Winnipeg via Minneapolis
Ave. Duration
3 h 55 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$300 - $1,200
Flights from Chicago Midway to Winnipeg via Minneapolis
Ave. Duration
4 h 50 min
When
Every day
Estimated price
$220 - $850
Flights from Chicago Midway to Winnipeg via Detroit, Minneapolis
Ave. Duration
6 h 52 min
When
Every day
Estimated price
$220 - $850
Flights from Chicago Midway to Winnipeg via Detroit, Toronto
Ave. Duration
7 h 34 min
When
Every day
Estimated price
$220 - $900
Air Canada
Website
aircanada.com
Flights from Chicago O'Hare to Winnipeg
Ave. Duration
2 h 19 min
When
Every day
Estimated price
$240 - $1,200
Flights from Chicago O'Hare to Winnipeg via Toronto
Ave. Duration
5 h 6 min
When
Every day
Estimated price
$250 - $1,300
United Airlines
Website
united.com
Flights from Chicago O'Hare to Winnipeg
Ave. Duration
2 h 19 min
When
Every day
Estimated price
$240 - $1,200
Flights from Chicago O'Hare to Winnipeg via Toronto
Ave. Duration
5 h 24 min
When
Every day
Estimated price
$250 - $1,300
Train operators
Amtrak
Rome2rio's guide to Amtrak
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Chicago Union Station Amtrak to St. Paul-Minneapolis Union Depot Amtrak
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
Schedules 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
Schedules at
jeffersonlines.com
Bus from Milwaukee to Minneapolis, MN
Ave. Duration
8 h 10 min
Frequency
Hourly
Estimated price
$70 - $100
Schedules at
jeffersonlines.com
Greyhound USA
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
1 h 50 min
Frequency
Every 30 minutes
Estimated price
$15 - $35
Website
greyhound.com
Economy
$15 - $23
Flexible
$27 - $35

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