There are 11 ways to get from Oakville 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 Toronto, fly to Chicago O'Hare  •  5 h 20 min

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

$112 - $418

Cheapest option

Bus Greyhound Canada  •  12 h 25 min

  1. Take the bus from Toronto, ON to Chicago, IL 5515 / ...

$54 - $133

9 alternative options

Train to Billy Bishop Toronto City, fly to Chicago Midway  •  5 h 4 min

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

$111 - $420

Train, bus to Buffalo, fly to Chicago Midway  •  6 h 56 min

  1. Take the train from Oakville to Niagara Falls
  2. Take the bus from Niagara Falls, On to Buffalo, Ny
  3. Fly from Buffalo (BUF) to Chicago Midway (MDW) BUF - MDW

$152 - $508

Train, bus to Buffalo, fly to Chicago O'Hare  •  7 h 13 min

  1. Take the train from Oakville to Niagara Falls
  2. Take the bus from Niagara Falls, On to Buffalo, Ny
  3. Fly from Buffalo (BUF) to Chicago O'Hare (ORD) BUF - ORD

$142 - $479

Fly Toronto to Chicago Midway  •  6 h 30 min

  1. Fly from Toronto (YYZ) to Chicago Midway (MDW) YYZ - MDW

$122 - $967

Fly Toronto to Milwaukee, train  •  7 h 23 min

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

$177 - $544

Train via Detroit Amtrak  •  9 h 56 min

  1. Take the train from Oakville to Windsor VIA Rail
  2. Take the train from Detroit Amtrak to Chicago Union Station Wolverine

$89 - $249

Bus Greyhound USA  •  12 h 37 min

  1. Take the bus from Toronto, On to Chicago, Il 5515 / ...

$59 - $196

Train  •  15 h 45 min

  1. Take the train from Oakville to Buffalo VIA Rail
  2. Take the train from Buffalo Depew Station Amtrak to Chicago Union Station Lake Shore Limited

$103 - $299

Drive  •  8 h 23 min

  1. Drive from Oakville to Chicago 498.7 miles

$65 - $100

Questions & Answers

No, there is no direct bus from Oakville to Chicago. However, there are services departing from Oakville, ON and arriving at Chicago, IL via Toronto, ON. The journey, including transfers, takes approximately 12 h 25 min.

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No, there is no direct train from Oakville to Chicago station. However, there are services departing from Oakville and arriving at Chicago Union Station via Buffalo Depew Station Amtrak. The journey, including transfers, takes approximately 15 h 45 min.

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The distance between Oakville and Chicago is 672 km. The road distance is 798 km.

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The best way to get from Oakville to Chicago without a car is to bus which takes 12 h 25 min and costs .

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It takes approximately 5 h 20 min to get from Oakville to Chicago, including transfers.

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

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

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The best way to get from Oakville to Chicago is to fly which takes 6 h 30 min and costs . Alternatively, you can train, which costs and takes 9 h 56 min, you could also bus, which costs and takes 12 h 25 min.

Mode details

The quickest flight from Toronto Airport to Chicago O'Hare Airport is the direct flight which takes 1 h 42 min.

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Oakville to Chicago bus services, operated by Greyhound Canada, arrive at Chicago, IL station.

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Map of how to get from Oakville to Chicago.
Launch map view
  • Distance: 420.3 miles
  • Duration: 5 h 20 min

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

Delta, Air Canada and two other airlines fly from Oakville to Chicago hourly. Alternatively, you can take a train from Oakville to Chicago via Windsor and Detroit Amtrak in around 9 h 56 min.

Airlines
United Airlines
Website
united.com
Flights from Toronto to Chicago O'Hare
Ave. Duration
1 h 51 min
When
Every day
Estimated price
$140 - $700
Flights from Buffalo to Chicago O'Hare
Ave. Duration
1 h 49 min
When
Every day
Estimated price
$140 - $750
Flights from Buffalo to Chicago O'Hare via Washington Dulles
Ave. Duration
4 h 7 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
3 h 50 min
When
Every day
Estimated price
$330 - $1,000
Delta
Website
delta.com
Flights from Toronto to Chicago O'Hare via Detroit
Ave. Duration
3 h 37 min
When
Every day
Estimated price
$170 - $1,000
Flights from Buffalo to Chicago Midway via Detroit
Ave. Duration
3 h 27 min
When
Every day
Estimated price
$130 - $800
Flights from Buffalo to Chicago O'Hare via Detroit
Ave. Duration
3 h 53 min
When
Every day
Estimated price
$130 - $800
Flights from Toronto to Chicago Midway via Detroit
Ave. Duration
4 h 1 min
When
Every day
Estimated price
$110 - $900
Flights from Toronto to Chicago Midway via Minneapolis
Ave. Duration
5 h 38 min
When
Every day
Estimated price
$160 - $1,100
Flights from Toronto to Chicago Midway via Atlanta
Ave. Duration
5 h 45 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$180 - $1,200
Flights from Toronto to Milwaukee via Detroit
Ave. Duration
3 h 35 min
When
Every day
Estimated price
$270 - $950
Air Canada
Website
aircanada.com
Flights from Toronto to Chicago O'Hare
Ave. Duration
1 h 46 min
When
Every day
Estimated price
$130 - $700
Flights from Buffalo to Chicago O'Hare
Ave. Duration
1 h 49 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
Southwest Airlines
Website
southwest.com
Flights from Buffalo to Chicago Midway
Ave. Duration
1 h 40 min
When
Every day
Estimated price
$160 - $750
Flights from Buffalo to Chicago Midway via Baltimore
Ave. Duration
4 h 15 min
When
Every day
Estimated price
$160 - $750
American Airlines
Website
aa.com
Flights from Toronto to Chicago O'Hare
Ave. Duration
2 h
When
Every day
Estimated price
$130 - $800
Flights from Buffalo to Chicago O'Hare
Ave. Duration
1 h 59 min
When
Every day
Estimated price
$120 - $650
Flights from Toronto to Milwaukee via Chicago O'Hare
Ave. Duration
4 h 10 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 46 min
When
Every day
Estimated price
$120 - $700
Train operators
VIA Rail
Phone
+1 1 888 842-7245
Website
viarail.ca
Train from Oakville to Toronto
Ave. Duration
22 min
Frequency
Every 30 minutes
Estimated price
$20 - $55
Website
viarail.ca
Escape
$20 - $28
Economy
$22 - $35
Economy Plus
$35 - $55
Business
$30 - $45
Business Plus/Sleeper
$55 - $85
Train from Oakville to Niagara Falls
Ave. Duration
1 h 32 min
Frequency
Every 3 hours
Estimated price
$24 - $70
Website
viarail.ca
Escape
$24 - $35
Economy
$30 - $45
Economy Plus
$45 - $70
Business
$40 - $60
Business Plus/Sleeper
$75 - $110
Train from Oakville to Windsor
Ave. Duration
3 h 45 min
Frequency
Every 30 minutes
Estimated price
$35 - $120
Website
viarail.ca
Escape
$35 - $55
Economy
$55 - $80
Economy Plus
$85 - $120
Business
$80 - $120
Business Plus/Sleeper
$150 - $210
Train from Oakville to Buffalo
Ave. Duration
4 h 15 min
Frequency
Every 3 hours
Estimated price
$27 - $80
Website
viarail.ca
Escape
$27 - $40
Economy
$35 - $50
Economy Plus
$55 - $80
Business
$50 - $75
Business Plus/Sleeper
$95 - $140
GO Transit
Phone
+1 888-438-6646
Website
gotransit.com
Train from Oakville GO to Union Station
Ave. Duration
45 min
Frequency
Every 30 minutes
Estimated price
$5 - $8
Website
GO Transit
Train from Oakville GO to Niagara Falls GO
Ave. Duration
1 h 35 min
Frequency
4 times a week
Estimated price
$9 - $13
Website
GO Transit
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
$25
Website
amtrak.com
Coach Seat
$25
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
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 Niagara Falls, On to Buffalo, Ny
Ave. Duration
1 h 35 min
Frequency
Every 30 minutes
Estimated price
$9 - $20
Website
greyhound.com
Economy
$9 - $14
Flexible
$16 - $20
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
Megabus Canada
Phone
1-866-488-4452
Email
canada-info@coachcanada.com
Website
ca.megabus.com
Bus from Niagara Falls, ON to Buffalo, NY
Ave. Duration
1 h
Frequency
4 times a day
Estimated price
$9 - $14
Book at
megabus.ca
Greyhound Canada
Phone
+1 1-800-661-8747
Email
Canada.info@greyhound.ca
Website
greyhound.ca
Bus from Niagara Falls, ON to Buffalo, NY
Ave. Duration
31 min
Frequency
3 times a day
Estimated price
$8 - $23
Website
Greyhound.ca
Advanced Purchase
$8 - $13
Online Fare
$8 - $21
Standard Fare
$16 - $23
Refundable
$19 - $28
Bus from Toronto, ON to Chicago, IL
Ave. Duration
10 h 45 min
Frequency
4 times a day
Estimated price
$45 - $120
Website
Greyhound.ca
Advanced Purchase
$45 - $70
Online Fare
$60 - $90
Standard Fare
$75 - $120
Refundable
$85 - $130

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More Questions & Answers

Chicago is 1 h behind Oakville. It is currently 1:58 AM in Oakville and 12:58 AM in Chicago.

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

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Yes, the driving distance between Oakville to Chicago is 798 km. It takes approximately 8 h 23 min to drive from Oakville to Chicago.

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

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Book your Oakville to Chicago bus tickets online with Busbud.

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There are 580+ hotels available in Chicago. Prices start at $103 USD per night.

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