There are 10 ways to get from Oshawa to Chicago by train, plane, 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

Train to Billy Bishop Toronto City, fly to Chicago Midway  •  5 h 11 min

  1. Take the train from Oshawa to Toronto
  2. Fly from Billy Bishop Toronto City (YTZ) to Chicago Midway (MDW) YTZ - MDW

$127 - $425

Cheapest option

Bus Greyhound Canada  •  13 h 36 min

  1. Take the bus from Oshawa, ON to Toronto, ON 5769 / ...
  2. Take the bus from Toronto, ON to Chicago - Amtrak 5531

$55 - $146

8 alternative options

Train to Toronto, fly to Chicago O'Hare  •  5 h 32 min

  1. Take the train from Oshawa to Toronto
  2. Fly from Toronto (YYZ) to Chicago O'Hare (ORD) YYZ - ORD

$128 - $423

Train, bus to Buffalo, fly to Chicago Midway  •  7 h 31 min

  1. Take the train from Oshawa to Toronto
  2. Take the bus from Toronto, ON to Buffalo, NY
  3. Fly from Buffalo (BUF) to Chicago Midway (MDW) BUF - MDW

$176 - $503

Train, bus to Buffalo, fly to Chicago O'Hare  •  7 h 51 min

  1. Take the train from Oshawa to Toronto
  2. Take the bus from Toronto, ON to Buffalo, NY
  3. Fly from Buffalo (BUF) to Chicago O'Hare (ORD) BUF - ORD

$166 - $474

Train to Toronto, fly to Milwaukee, train  •  7 h 41 min

  1. Take the train from Oshawa to Toronto
  2. Fly from Toronto (YYZ) to Milwaukee (MKE) YYZ - MKE
  3. Take the train from Milwaukee Intermodal Station to Chicago Union Station

$196 - $584

Train via Detroit Amtrak  •  11 h 8 min

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

$113 - $320

Bus Greyhound USA  •  14 h 31 min

  1. Take the bus from Oshawa Bus Terminal to York Mills Bus Terminal 92
  2. Take the bus from Toronto, On to Chicago, Il 5515

$60 - $151

Train  •  18 h 7 min

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

$129 - $375

Drive  •  9 h 19 min

  1. Drive from Oshawa to Chicago 551.6 miles

$70 - $110

Questions & Answers

The cheapest way to get from Oshawa to Chicago is to drive which costs $90 - $140 and takes 9 h 19 min.

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The quickest way to get from Oshawa to Chicago is to train and fly which costs $160 - $550 and takes 5 h 11 min.

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No, there is no direct bus from Oshawa to Chicago. However, there are services departing from Oshawa, ON and arriving at Chicago - Amtrak via Toronto, ON. The journey, including transfers, takes approximately 13 h 36 min.

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The distance between Oshawa and Chicago is 749 km. The road distance is 882.6 km.

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The best way to get from Oshawa to Chicago without a car is to bus which takes 13 h 36 min and costs $70 - $190.

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It takes approximately 5 h 11 min to get from Oshawa to Chicago, including transfers.

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Oshawa to Chicago bus services, operated by Greyhound Canada, depart from Oshawa, ON station.

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The best way to get from Oshawa to Chicago is to train which takes 11 h 8 min and costs $140 - $420. Alternatively, you can bus, which costs $70 - $190 and takes 13 h 36 min.

Mode details

The quickest flight from Billy Bishop Toronto City Airport to Chicago Midway Airport is the direct flight which takes 1 h 47 min.

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Oshawa to Chicago bus services, operated by Greyhound Canada, arrive at Chicago - Amtrak station.

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Map of how to get from Oshawa to Chicago.
Launch map view
  • Distance: 468.3 miles
  • Duration: 5 h 11 min

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

You can take a train from Oshawa to Chicago via Toronto, Windsor, and Detroit Amtrak in around 11 h 8 min. Alternatively, you can take a bus from Oshawa to Chicago via Toronto, ON in around 13 h 36 min.

Airlines
United Airlines
Website
united.com
Flights from Toronto to Chicago O'Hare
Ave. Duration
1 h 53 min
When
Every day
Estimated price
$140 - $700
Flights from Buffalo to Chicago O'Hare
Ave. Duration
1 h 48 min
When
Every day
Estimated price
$140 - $750
Flights from Buffalo to Chicago O'Hare via Washington Dulles
Ave. Duration
4 h 8 min
When
Every day
Estimated price
$140 - $750
Flights from Toronto to Milwaukee
Ave. Duration
1 h 35 min
When
Every day
Estimated price
$370 - $1,600
Flights from Toronto to Milwaukee via Chicago O'Hare
Ave. Duration
4 h 10 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$330 - $1,000
Air Canada
Website
aircanada.com
Flights from Toronto to Chicago O'Hare
Ave. Duration
1 h 50 min
When
Every day
Estimated price
$130 - $700
Flights from Buffalo to Chicago O'Hare
Ave. Duration
1 h 48 min
When
Every day
Estimated price
$140 - $750
Flights from Toronto to Milwaukee
Ave. Duration
1 h 35 min
When
Every day
Estimated price
$370 - $1,600
Delta
Website
delta.com
Flights from Toronto to Chicago O'Hare via Detroit
Ave. Duration
3 h 33 min
When
Every day
Estimated price
$170 - $1,000
Flights from Buffalo to Chicago Midway via Detroit
Ave. Duration
3 h 31 min
When
Every day
Estimated price
$130 - $800
Flights from Buffalo to Chicago O'Hare via Detroit
Ave. Duration
3 h 43 min
When
Every day
Estimated price
$130 - $800
Flights from Toronto to Milwaukee via Detroit
Ave. Duration
3 h 16 min
When
Every day
Estimated price
$270 - $950
Southwest Airlines
Website
southwest.com
Flights from Buffalo to Chicago Midway
Ave. Duration
1 h 38 min
When
Every day
Estimated price
$160 - $750
Flights from Buffalo to Chicago Midway via Baltimore
Ave. Duration
4 h 3 min
When
Saturday and Sunday
Estimated price
$160 - $750
American Airlines
Website
aa.com
Flights from Toronto to Chicago O'Hare
Ave. Duration
1 h 58 min
When
Every day
Estimated price
$130 - $800
Flights from Buffalo to Chicago O'Hare
Ave. Duration
1 h 55 min
When
Every day
Estimated price
$120 - $650
Flights from Toronto to Milwaukee via Chicago O'Hare
Ave. Duration
4 h 5 min
When
Every day
Estimated price
$260 - $750
Porter Airlines
Website
flyporter.com
Flights from Billy Bishop Toronto City to Chicago Midway
Ave. Duration
1 h 47 min
When
Every day
Estimated price
$120 - $700
Train operators
VIA Rail
Phone
+1 1 888 842-7245
Website
viarail.ca
Train from Oshawa to Toronto
Ave. Duration
29 min
Frequency
Every 20 minutes
Estimated price
$21 - $60
Website
viarail.ca
Escape
$21 - $30
Economy
$25 - $35
Economy Plus
$40 - $60
Business
$35 - $50
Business Plus/Sleeper
$65 - $90
Train from Toronto to Windsor
Ave. Duration
4 h 9 min
Frequency
Every 30 minutes
Estimated price
$40 - $130
Website
viarail.ca
Escape
$40 - $60
Economy
$60 - $85
Economy Plus
$90 - $130
Business
$90 - $130
Business Plus/Sleeper
$160 - $230
Train from Toronto to Buffalo
Ave. Duration
4 h 39 min
Frequency
Every 3 hours
Estimated price
$30 - $90
Website
viarail.ca
Escape
$30 - $45
Economy
$40 - $60
Economy Plus
$65 - $90
Business
$55 - $85
Business Plus/Sleeper
$100 - $150
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 Milwaukee Intermodal Station to Chicago Union Station
Ave. Duration
1 h 29 min
Frequency
Every 4 hours
Estimated price
$28 - $60
Website
amtrak.com
Coach Seat
$28 - $45
Flexi Coach Seat
$50 - $75
Business Coach Seat
$40 - $60
Room
$150 - $220
Train from Detroit Amtrak to Chicago Union Station
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
Ave. Duration
10 h 30 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
Megabus Canada
Greyhound Canada
Phone
+1 1-800-661-8747
Email
Canada.info@greyhound.ca
Website
greyhound.ca
Bus from Toronto, ON to Buffalo, NY
Ave. Duration
1 h 37 min
Frequency
Once daily
Estimated price
$14 - $40
Website
Greyhound.ca
Advanced Purchase
$14 - $21
Online Fare
$16 - $35
Standard Fare
$25 - $40
Refundable
$29 - $45
Bus from Oshawa, ON to Toronto, ON
Ave. Duration
1 h 1 min
Frequency
Twice daily
Estimated price
$10 - $26
Website
Greyhound.ca
Advanced Purchase
$10 - $15
Online Fare
$10 - $24
Standard Fare
$18 - $26
Refundable
$21 - $35
Bus from Toronto, ON to Chicago - Amtrak
Ave. Duration
11 h 35 min
Frequency
Once daily
Estimated price
$45 - $120
Website
Greyhound.ca
Advanced Purchase
$45 - $70
Online Fare
$60 - $90
Standard Fare
$80 - $120
Refundable
$85 - $130
GO Transit
Phone
+1 888-438-6646
Website
gotransit.com
Bus from Oshawa Bus Terminal to York Mills Bus Terminal
Ave. Duration
1 h 15 min
Frequency
Every 30 minutes
Estimated price
$6 - $9
Schedules at
gotransit.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 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

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More Questions & Answers

Chicago is 1 h behind Oshawa. It is currently 11:22 AM in Oshawa and 10:22 AM in Chicago.

Yes, the driving distance between Oshawa to Chicago is 883 km. It takes approximately 9 h 19 min to drive from Oshawa to Chicago.

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Porter Airlines offers flights from Billy Bishop Toronto City Airport to Chicago Midway Airport.

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Book your Oshawa to Chicago bus tickets online with Busbud and Busbud.

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There are 574+ hotels available in Chicago. Prices start at $104 USD per night.

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