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There are 9 ways to get from Winnipeg to Chicago by plane, train, bus, night 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 to Chicago O'Hare  •  5h 56m

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

$205 - $488

Cheapest option

Fly to Milwaukee, train  •  9h 30m

  1. Fly from Winnipeg (YWG) to Milwaukee (MKE) YWG - MKE
  2. Take the train from Milwaukee Intermodal Station to Chicago Union Station

$170 - $1,144

7 alternative options

Fly to Chicago Midway  •  7h 43m

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

$215 - $477

Fly to South Bend, bus  •  9h 21m

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

$308 - $1,238

Train via Detroit Amtrak Station  •  2 days 1h

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

$314 - $590

Train, night bus  •  2 days 3h

  1. Take the train from Winnipeg to Toronto VIA Rail
  2. Take the night bus from Toronto, On to Chicago Amtrak, Il 5531

$256 - $471

Train, bus  •  2 days 3h

  1. Take the train from Winnipeg to Toronto VIA Rail
  2. Take the bus from Toronto, ON - 610 Bay Street to Chicago, IL - Amtrack Station Toronto

$251 - $461

Train  •  2 days 7h

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

$323 - $653

Drive  •  14h 33m

  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 14h 33m.

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The quickest way to get from Winnipeg to Chicago is to fly which costs $260 - $650 and takes 5h 56m.

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No, there is no direct train from Winnipeg to Chicago station. However, there are services departing from Winnipeg and arriving at Chicago Union Station via Toronto and Buffalo Depew Station. The journey, including transfers, takes approximately 2 days 7h.

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The distance between Winnipeg and Chicago is 1154 km. The road distance is 1389.9 km.

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The best way to get from Winnipeg to Chicago without a car is to train and night bus which takes 2 days 3h and costs $330 - $650.

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It takes approximately 5h 56m to get from Winnipeg to Chicago, including transfers.

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Winnipeg to Chicago train services, operated by VIA Rail, depart from Winnipeg station.

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The best way to get from Winnipeg to Chicago is to fly which takes 5h 56m and costs $260 - $650. Alternatively, you can train, which costs $410 - $800 and takes 2 days 1h.

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The quickest flight from Winnipeg Airport to Chicago O'Hare Airport is the direct flight which takes 2h 33m.

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Winnipeg to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.

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Map of how to get from Winnipeg to Chicago.
Launch map view
  • Distance: 721.2 miles
  • Duration: 5h 56m

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 train from Winnipeg to Chicago via Toronto, Windsor, and Detroit Amtrak Station in around 2 days 1h.

Airlines
Delta
Website
delta.com
Flights from Winnipeg to Chicago O'Hare via Minneapolis
Ave. Duration
4h 29m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$300 - $1,200
Flights from Winnipeg to Chicago Midway via Minneapolis
Ave. Duration
4h 45m
When
Every day
Estimated price
$220 - $850
Flights from Winnipeg to Chicago Midway via Minneapolis, Detroit
Ave. Duration
9h 48m
When
Every day
Estimated price
$220 - $850
Flights from Winnipeg to Chicago Midway via Toronto, Detroit
Ave. Duration
7h 42m
When
Sunday
Estimated price
$190 - $800
Flights from Winnipeg to Milwaukee via Minneapolis
Ave. Duration
4h 24m
When
Every day
Estimated price
$160 - $1,200
Flights from Winnipeg to Milwaukee via Minneapolis, Detroit
Ave. Duration
8h 16m
When
Every day
Estimated price
$210 - $1,400
Flights from Winnipeg to South Bend via Minneapolis
Ave. Duration
4h 37m
When
Every day
Estimated price
$260 - $1,800
Flights from Winnipeg to South Bend via Minneapolis, Detroit
Ave. Duration
8h 4m
When
Every day
Estimated price
$300 - $2,000
Flights from Winnipeg to South Bend via Minneapolis, Atlanta
Ave. Duration
8h 51m
When
Every day
Estimated price
$400 - $2,500
Flights from Winnipeg to South Bend via Toronto, Detroit
Ave. Duration
7h 34m
When
Tuesday, Wednesday, Thursday and Friday
Estimated price
$290 - $1,200
United Airlines
Website
united.com
Flights from Winnipeg to Chicago O'Hare
Ave. Duration
2h 41m
When
Every day
Estimated price
$240 - $1,200
Flights from Winnipeg to Chicago O'Hare via Toronto
Ave. Duration
5h 51m
When
Monday to Saturday
Estimated price
$250 - $1,300
Flights from Winnipeg to Milwaukee via Chicago O'Hare
Ave. Duration
4h 33m
When
Every day
Estimated price
$140 - $1,100
Flights from Winnipeg to Milwaukee via Toronto
Ave. Duration
6h 4m
When
Monday to Friday
Estimated price
$270 - $1,800
Flights from Winnipeg to South Bend via Chicago O'Hare
Ave. Duration
7h 20m
When
Every day
Estimated price
$210 - $1,600
Air Canada
Website
aircanada.com
Flights from Winnipeg to Chicago O'Hare
Ave. Duration
2h 41m
When
Every day
Estimated price
$240 - $1,200
Flights from Winnipeg to Chicago O'Hare via Toronto
Ave. Duration
5h 53m
When
Monday to Friday
Estimated price
$250 - $1,300
Flights from Winnipeg to Milwaukee via Toronto
Ave. Duration
6h 4m
When
Monday to Friday
Estimated price
$270 - $1,800
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
+1 215-856-7924
Website
amtrak.com
Train from Milwaukee Intermodal Station to Chicago Union Station
Ave. Duration
1h 29m
Frequency
Every 4 hours
Estimated price
$25
Website
amtrak.com
Coach Seat
$25
Train from Detroit Amtrak Station to Chicago Union Station
Ave. Duration
4h 59m
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 to Chicago Union Station
Ave. Duration
10h 30m
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
VIA Rail
Phone
+1 1 888 842-7245
Website
viarail.ca
Train from Winnipeg to Toronto
Ave. Duration
37h 59m
Frequency
Twice a week
Estimated price
$200 - $340
Website
viarail.ca
Escape
$170 - $190
Economy
$200 - $280
EconomyPlus
$240 - $340
Business
$370 - $550
Train from Toronto to Windsor
Ave. Duration
3h 59m
Frequency
4 times a day
Estimated price
$60 - $120
Website
viarail.ca
Escape
$40 - $60
Economy
$60 - $90
EconomyPlus
$80 - $120
Business
$100 - $140
Train from Toronto to Buffalo
Ave. Duration
4h 39m
Frequency
Once daily
Estimated price
$45 - $95
Website
viarail.ca
Escape
$25 - $50
Economy
$45 - $65
EconomyPlus
$65 - $95
Business
$70 - $95
Bus operators
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 South Bend, In to Chicago, Il
Ave. Duration
1h 10m
Frequency
Once daily
Estimated price
$15 - $35
Website
greyhound.com
Economy
$15 - $23
Flexible
$27 - $35
Night bus from Toronto, On to Chicago Amtrak, Il
Ave. Duration
12h 35m
Frequency
Once daily
Estimated price
$50 - $130
Website
greyhound.com
Economy
$50 - $85
Flexible
$100 - $130
Greyhound Canada
Phone
+1 1-800-661-8747
Email
Canada.info@greyhound.ca
Website
greyhound.ca
Bus from Toronto, ON - 610 Bay Street to Chicago, IL - Amtrack Station
Ave. Duration
12h 35m
Frequency
Once daily
Estimated price
$45 - $120
Website
Greyhound.ca
Advanced Purchase
$45 - $70
Online Fare
$60 - $90
Standard Fare
$75 - $120
Refundable
$85 - $130

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.

More Questions & Answers

Yes, the driving distance between Winnipeg to Chicago is 1390 km. It takes approximately 14h 33m to drive from Winnipeg to Chicago.

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

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There are 763+ hotels available in Chicago. Prices start at $75 USD per night.

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The best way to get from Winnipeg to Winnipeg Airport is to line 20 bus which takes 35m and costs $4.

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