There are 8 ways to get from Winnipeg to Chicago by plane, bus, train 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 to Chicago O'Hare  •  5 h 28 min

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

$205 - $488

Cheapest option

Bus  •  44 h 38 min

  1. Take the bus from Winnipeg, MB to Toronto, ON - 610 Bay Street 5150
  2. Take the bus from Toronto, On to Chicago, Il 5515

$153 - $403

6 alternative options

Fly to Chicago Midway  •  6 h 50 min

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

$215 - $477

Fly to South Bend, bus  •  9 h 25 min

  1. Fly from Winnipeg (YWG) to South Bend (SBN) YWG - SBN
  2. Take the bus from South Bend, In to Chicago, Il

$228 - $1,638

Bus, Amtrak Thruway  •  38 h 34 min

  1. Take the bus from Winnipeg, MB to Sault Ste Marie, ON
  2. Take the Amtrak Thruway from Sault Ste. Marie, MI to Kalamazoo, MI - Amtrak
  3. Take the bus from Kalamazoo to Chicago Union Station

Train via Detroit Amtrak  •  44 h 39 min

  1. Take the train from Winnipeg to Toronto
  2. Take the train from Toronto to Windsor
  3. Take the train from Detroit Amtrak to Chicago Union Station Amtrak

$227 - $731

Train  •  2 days 2 h

  1. Take the train from Winnipeg to Toronto
  2. Take the train from Toronto to Buffalo
  3. Take the train from Buffalo Depew Station Amtrak to Chicago Union Station Amtrak

$240 - $779

Drive  •  14 h 33 min

  1. Drive from Winnipeg to Chicago 868.7 miles

$110 - $170

Questions & Answers

The cheapest way to get from Winnipeg to Chicago is to drive which costs $150 - $220 and takes 14 h 33 min.

More details

The quickest way to get from Winnipeg to Chicago is to fly which takes 5 h 28 min and costs $270 - $650.

More details

The distance between Winnipeg and Chicago is 1154 km. The road distance is 1390 km.

Get driving directions

It takes approximately 5 h 28 min to get from Winnipeg to Chicago, including transfers.

More details

No, there is no direct bus from Winnipeg to Chicago. However, there are services departing from Northbound Vaughan at Portage North and arriving at Chicago, Il via Winnipeg, MB and Toronto, On. The journey, including transfers, takes approximately 44 h 38 min.

More details

No, there is no direct train from Winnipeg to Chicago. However, there are services departing from Winnipeg and arriving at Chicago Union Station Amtrak via Toronto and Buffalo Depew Station Amtrak. The journey, including transfers, takes approximately 2 days 2 h.

More details

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

United Airlines, Delta and Air Canada fly from Winnipeg to Chicago every 4 hours. Alternatively, you can take a bus from Winnipeg to Chicago via Westbound Wellington at Airport Terminal, Winnipeg, MB, Sault Ste Marie, ON, Sault Ste. Marie, MI, Kalamazoo, MI - Amtrak, and Kalamazoo in around 38 h 34 min.

Airlines
Delta
Website
delta.com
Flights from Winnipeg to Chicago O'Hare via Minneapolis
Ave. Duration
4 h 54 min
When
Every day
Estimated price
$300 - $1,200
Flights from Winnipeg to Chicago Midway via Minneapolis
Ave. Duration
5 h 7 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$220 - $850
Flights from Winnipeg to Chicago Midway via Toronto, Detroit
Ave. Duration
7 h 16 min
When
Every day
Estimated price
$190 - $800
Flights from Winnipeg to South Bend via Minneapolis
Ave. Duration
4 h 58 min
When
Every day
Estimated price
$260 - $1,800
Flights from Winnipeg to South Bend via Minneapolis, Atlanta
Ave. Duration
8 h 56 min
When
Every day
Estimated price
$400 - $2,500
Flights from Winnipeg to South Bend via Minneapolis, Detroit
Ave. Duration
9 h 15 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$300 - $2,000
United Airlines
Website
united.com
Flights from Winnipeg to Chicago O'Hare
Ave. Duration
2 h 22 min
When
Every day
Estimated price
$240 - $1,200
Flights from Winnipeg to South Bend via Chicago O'Hare
Ave. Duration
5 h 27 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$210 - $1,600
Flights from Winnipeg to South Bend via Denver, Chicago O'Hare
Ave. Duration
9 h 55 min
When
Every day
Estimated price
$370 - $2,000
Air Canada
Website
aircanada.com
Flights from Winnipeg to Chicago O'Hare
Ave. Duration
2 h 22 min
When
Every day
Estimated price
$240 - $1,200
Flights from Winnipeg to Chicago O'Hare via Toronto
Ave. Duration
5 h 22 min
When
Every day
Estimated price
$250 - $1,300
Train operators
VIA Rail
Phone
+1 1 888 842-7245
Website
viarail.ca
Train from Winnipeg to Toronto
Ave. Duration
34 h
Frequency
3 times a day
Estimated price
$130 - $470
Website
viarail.ca
Escape
$130 - $190
Economy
$250 - $340
Economy Plus
$340 - $470
Business
$360 - $550
Business Plus/Sleeper
$650 - $900
Train from Toronto to Windsor
Ave. Duration
4 h 9 min
Frequency
Every 30 minutes
Estimated price
$40 - $130
Website
viarail.ca
Escape
$40 - $55
Economy
$60 - $85
Economy Plus
$90 - $130
Business
$85 - $130
Business Plus/Sleeper
$160 - $230
Train from Toronto to Buffalo
Ave. Duration
4 h 9 min
Frequency
Every 3 hours
Estimated price
$29 - $90
Website
viarail.ca
Escape
$29 - $45
Economy
$40 - $55
Economy Plus
$60 - $90
Business
$55 - $80
Business Plus/Sleeper
$100 - $150
Amtrak
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Detroit Amtrak to Chicago Union Station Amtrak
Ave. Duration
4 h 59 min
Frequency
3 times a day
Estimated price
$50 - $130
Website
amtrak.com
Coach Seat
$50 - $75
Flexi Coach Seat
$90 - $130
Business Coach Seat
$90 - $130
Room
$230 - $320
Train from Buffalo Depew Station Amtrak to Chicago Union Station Amtrak
Ave. Duration
10 h 31 min
Frequency
Twice daily
Estimated price
$75 - $220
Website
amtrak.com
Coach Seat
$75 - $120
Flexi Coach Seat
$140 - $200
Business Coach Seat
$150 - $220
Room
$330 - $460
Bus operators
Greyhound USA
Phone
+1 214-849-8100/1-800-231-2222
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from South Bend, In to Chicago, Il
Ave. Duration
1 h 10 min
Frequency
Every 3 hours
Estimated price
$15 - $35
Website
greyhound.com
Economy
$15 - $23
Flexible
$27 - $35
Bus from Toronto, On to Chicago, Il
Ave. Duration
11 h 45 min
Frequency
Hourly
Estimated price
$50 - $140
Website
greyhound.com
Economy
$50 - $85
Flexible
$100 - $140
Greyhound Canada
Phone
+1 1-800-661-8747
Email
Canada.info@greyhound.ca
Website
greyhound.ca
Bus from Winnipeg, MB to Sault Ste Marie, ON
Ave. Duration
21 h 50 min
Frequency
Once daily
Estimated price
$70 - $180
Website
Greyhound.ca
Advanced Purchase
$70 - $110
Online Fare
$95 - $140
Standard Fare
$120 - $180
Refundable
$130 - $190
Bus from Winnipeg, MB to Toronto, ON - 610 Bay Street
Ave. Duration
30 h 30 min
Frequency
Once daily
Estimated price
$100 - $260
Website
Greyhound.ca
Advanced Purchase
$100 - $160
Online Fare
$140 - $200
Standard Fare
$170 - $260
Refundable
$190 - $280
Indian Trails
Phone
+1 800-292-3831
Website
indiantrails.com
Bus from Kalamazoo to Chicago Union Station
Ave. Duration
3 h 15 min
Frequency
Twice daily
Estimated price
$22 - $30
Schedules at
indiantrails.com
Book at
webstore.indiantrails.com

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