There are 10 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

$126 - $418

Cheapest option

Bus Greyhound Canada  •  13 h 15 min

  1. Take the bus from Toronto, ON to Chicago - Amtrak 5531

$54 - $133

8 alternative options

Train to Toronto Island, fly to Chicago Midway  •  5 h 2 min

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

$125 - $420

Fly Toronto to Chicago Midway  •  6 h 49 min

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

$136 - $967

Train, train to Buffalo, fly to Chicago O'Hare  •  7 h 16 min

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

$176 - $516

Train, train to Buffalo, fly to Chicago Midway  •  7 h 4 min

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

$186 - $545

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 Amtrak Wolverine

$89 - $249

Bus Greyhound USA  •  13 h 11 min

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

$73 - $196

Train  •  15 h 16 min

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

$102 - $299

Drive  •  8 h 23 min

  1. Drive from Oakville to Chicago 498.7 miles

$65 - $100

Questions & Answers

The cheapest way to get from Oakville to Chicago is to drive which costs $85 - $130 and takes 8 h 23 min.

More details

The quickest way to get from Oakville to Chicago is to train and fly which costs $160 - $550 and takes 5 h 2 min.

More details

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

Get driving directions

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

More details

No, there is no direct bus from Oakville to Chicago. However, there are services departing from Oakville, ON and arriving at Chicago - Amtrak via Toronto, ON. The journey, including transfers, takes approximately 13 h 15 min.

More details

No, there is no direct train from Oakville to Chicago station. However, there are services departing from Oakville and arriving at Chicago Union Station Amtrak via Buffalo Depew Station Amtrak. The journey, including transfers, takes approximately 15 h 16 min.

More details

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

Delta, Air Canada and Southwest 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
Air Canada
Website
aircanada.com
Flights from Toronto to Chicago O'Hare
Ave. Duration
1 h 48 min
When
Every day
Estimated price
$130 - $700
Flights from Buffalo to Chicago O'Hare
Ave. Duration
1 h 46 min
When
Every day
Estimated price
$140 - $750
United Airlines
Website
united.com
Flights from Toronto to Chicago O'Hare
Ave. Duration
1 h 50 min
When
Every day
Estimated price
$140 - $700
Flights from Buffalo to Chicago O'Hare
Ave. Duration
1 h 46 min
When
Every day
Estimated price
$140 - $750
Flights from Buffalo to Chicago O'Hare via Washington Dulles
Ave. Duration
4 h 10 min
When
Every day
Estimated price
$140 - $750
Delta
Website
delta.com
Flights from Toronto to Chicago O'Hare via Detroit
Ave. Duration
3 h 29 min
When
Every day
Estimated price
$170 - $1,000
Flights from Toronto to Chicago Midway via Detroit
Ave. Duration
3 h 41 min
When
Every day
Estimated price
$110 - $900
Flights from Toronto to Chicago Midway via Minneapolis
Ave. Duration
5 h 21 min
When
Every day
Estimated price
$160 - $1,100
Flights from Toronto to Chicago Midway via Atlanta
Ave. Duration
5 h 42 min
When
Every day
Estimated price
$180 - $1,200
Flights from Buffalo to Chicago O'Hare via Detroit
Ave. Duration
3 h 41 min
When
Every day
Estimated price
$130 - $800
Flights from Buffalo to Chicago Midway via Detroit
Ave. Duration
3 h 36 min
When
Every day
Estimated price
$130 - $800
American Airlines
Website
aa.com
Flights from Toronto to Chicago O'Hare
Ave. Duration
1 h 59 min
When
Every day
Estimated price
$130 - $800
Flights from Buffalo to Chicago O'Hare
Ave. Duration
1 h 54 min
When
Every day
Estimated price
$120 - $650
Southwest Airlines
Website
southwest.com
Flights from Buffalo to Chicago Midway
Ave. Duration
1 h 38 min
When
Every day
Estimated price
$160 - $750
Porter Airlines
Website
flyporter.com
Flights from Toronto Island 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 - $30
Economy Plus
$35 - $55
Business
$30 - $45
Business Plus/Sleeper
$55 - $80
Train from Oakville to Niagara Falls Station
Ave. Duration
1 h 50 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 Niagara Falls Station to Buffalo
Ave. Duration
38 min
Frequency
Every 3 hours
Estimated price
$20 - $55
Website
viarail.ca
Escape
$20 - $29
Economy
$23 - $35
Economy Plus
$40 - $55
Business
$30 - $45
Business Plus/Sleeper
$60 - $85
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
3 h 45 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
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 Niagara Falls Amtrak to Buffalo Exchange Street Amtrak
Ave. Duration
36 min
Frequency
4 times a day
Estimated price
$21 - $40
Website
amtrak.com
Coach Seat
$21 - $35
Flexi Coach Seat
$35 - $55
Business Coach Seat
$27 - $40
Room
$130 - $180
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

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
Greyhound Canada
Phone
+1 1-800-661-8747
Email
Canada.info@greyhound.ca
Website
greyhound.ca
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
$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.