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There are 11 ways to get from Toronto to Chicago (Station) by plane, shuttle, train, 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 Billy Bishop Toronto City to Chicago Midway

  1. Fly from Billy Bishop Toronto City (YTZ) to Chicago Midway (MDW)

Cheapest option

Bus

  1. Take the bus from Toronto, ON to Windsor, ON
  2. Take the bus from Detroit to Chicago

9 alternative options

Fly Toronto to Chicago O'Hare

  1. Fly from Toronto (YYZ) to Chicago O'Hare (ORD)

Fly Toronto to Chicago Midway

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

Shuttle to Buffalo, fly to Chicago Midway

  1. Take a shuttle bus from Toronto Airport to Buffalo Airport
  2. Fly from Buffalo (BUF) to Chicago Midway (MDW)

Shuttle to Buffalo, fly to Chicago O'Hare

  1. Take a shuttle bus from Toronto Airport to Buffalo Airport
  2. Fly from Buffalo (BUF) to Chicago O'Hare (ORD)

Fly Toronto to Milwaukee, train

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

Train via Detroit

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

Train, shuttle, bus

  1. Take the train from Toronto Union Station to London VIA
  2. Take a shuttle bus from London, ON - 105, Wharncliffe Road South, Manor Park to Detroit Airport
  3. Take the bus from Ann Arbor, MI to Chicago, IL

Train

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

Drive

  1. Drive from Toronto to Chicago (Station)

Questions & Answers

The cheapest way to get from Toronto to Chicago (Station) is to bus which costs $70 - $120 and takes 12h 3m.

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The quickest way to get from Toronto to Chicago (Station) is to fly which costs $150 - $470 and takes 4h 37m.

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No, there is no direct bus from Toronto to Chicago (Station). However, there are services departing from Toronto, ON and arriving at Chicago via Windsor Transit Terminal and Detroit. The journey, including transfers, takes approximately 12h 3m.

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No, there is no direct train from Toronto station to Chicago (Station) station. However, there are services departing from Toronto Union Station and arriving at Chicago Union Station via Buffalo Depew Station. The journey, including transfers, takes approximately 16h 9m.

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The distance between Toronto and Chicago (Station) is 439 miles. The road distance is 522.5 miles.

Get driving directions

The best way to get from Toronto to Chicago (Station) without a car is to bus which takes 12h 3m and costs $70 - $120.

More details

It takes approximately 4h 37m to get from Toronto to Chicago (Station), including transfers.

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Toronto to Chicago (Station) bus services, operated by Rider Express, depart from Toronto, ON station.

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Toronto to Chicago (Station) train services, operated by VIA Rail, depart from Toronto Union Station.

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The best way to get from Toronto to Chicago (Station) is to fly which takes 4h 37m and costs $150 - $470. Alternatively, you can train via Detroit, which costs $130 - $260 and takes 10h 36m, you could also bus, which costs $70 - $120 and takes 12h 3m.

Mode details

Map of how to get from Toronto to Chicago (Station).
Launch map view
  • Distance: 438.7 miles
  • Duration: 4h 37m

What companies run services between Toronto, ON, Canada and Chicago (Station), IL, USA?

Porter Airlines flies from Toronto to Chicago (Station) twice daily. Alternatively, you can take a train from Toronto to Chicago (Station) via Windsor and Detroit in around 10h 36m.

Airlines
Delta
Website
delta.com
Flights from Toronto to Chicago O'Hare via Detroit
Ave. Duration
3h 48m
When
Every day
Estimated price
$65 - $140
Flights from Toronto to Chicago Midway via Detroit
Ave. Duration
6h 27m
When
Every day
Estimated price
$100 - $200
Flights from Toronto to Chicago Midway via Atlanta
Ave. Duration
6h 38m
When
Every day
Estimated price
$160 - $310
Flights from Toronto to Chicago Midway via Minneapolis
Ave. Duration
7h 41m
When
Tuesday and Thursday
Estimated price
$140 - $240
Flights from Buffalo to Chicago Midway via Detroit
Ave. Duration
3h 44m
When
Every day
Estimated price
$90 - $180
Flights from Buffalo to Chicago O'Hare via Detroit
Ave. Duration
4h 5m
When
Every day
Estimated price
$60 - $120
Flights from Toronto to Milwaukee via Detroit
Ave. Duration
3h 40m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$85 - $170
United Airlines
Website
united.com
Flights from Toronto to Chicago O'Hare
Ave. Duration
1h 58m
When
Every day
Estimated price
$150 - $420
Flights from Buffalo to Chicago O'Hare
Ave. Duration
2h 2m
When
Every day
Estimated price
$95 - $340
Flights from Buffalo to Chicago O'Hare via Washington Dulles
Ave. Duration
4h 33m
When
Every day
Estimated price
$95 - $340
Flights from Toronto to Milwaukee
Ave. Duration
1h 35m
When
Every day
Estimated price
$140 - $550
Flights from Toronto to Milwaukee via Chicago O'Hare
Ave. Duration
3h 51m
When
Every day
Estimated price
$250 - $600
Air Canada
Website
aircanada.com
Flights from Toronto to Chicago O'Hare
Ave. Duration
1h 53m
When
Every day
Estimated price
$130 - $430
Flights from Buffalo to Chicago O'Hare
Ave. Duration
2h 2m
When
Every day
Estimated price
$95 - $340
Flights from Toronto to Milwaukee
Ave. Duration
1h 35m
When
Every day
Estimated price
$140 - $550
Flights from Toronto to Milwaukee via Chicago O'Hare
Ave. Duration
3h 47m
When
Every day
Estimated price
$150 - $550
Southwest Airlines
Website
southwest.com
Flights from Toronto to Chicago Midway via Pittsburgh
Ave. Duration
3h 45m
When
Saturday and Sunday
Estimated price
$100 - $390
Flights from Toronto to Chicago Midway via Columbus
Ave. Duration
4h
When
Saturday
Estimated price
$190 - $700
Flights from Toronto to Chicago Midway via Detroit
Ave. Duration
4h 5m
When
Monday to Friday
Estimated price
$95 - $360
Flights from Toronto to Chicago Midway via Cleveland
Ave. Duration
4h 20m
When
Saturday
Estimated price
$95 - $370
Flights from Buffalo to Chicago Midway
Ave. Duration
1h 53m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$170 - $260
Flights from Buffalo to Chicago Midway via Baltimore
Ave. Duration
4h 25m
When
Monday to Friday
Estimated price
$170 - $260
Flights from Buffalo to Chicago O'Hare via Baltimore
Ave. Duration
4h 30m
When
Monday to Friday
Estimated price
$150 - $470
American Airlines
Website
aa.com
Flights from Toronto to Chicago O'Hare
Ave. Duration
2h 6m
When
Every day
Estimated price
$180 - $550
Flights from Buffalo to Chicago O'Hare
Ave. Duration
1h 57m
When
Every day
Estimated price
$95 - $420
Flights from Buffalo to Chicago O'Hare via Philadelphia
Ave. Duration
4h 44m
When
Sunday
Estimated price
$95 - $420
Porter Airlines
Website
flyporter.com
Flights from Billy Bishop Toronto City to Chicago Midway
Ave. Duration
1h 50m
When
Every day
Estimated price
$120 - $350
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
+1 800-872-7245
Website
amtrak.com
Train from Milwaukee to Chicago Union Station
Ave. Duration
1h 29m
Frequency
Every 4 hours
Estimated price
$27 - $40
Schedules at
amtrak.com
Book at
amtrak.com
Coach Seat
$27 - $40
Premium
$180 - $260
Flexi Coach Seat
$40 - $60
Business Seat
$35 - $55
Train from Detroit to Chicago Union Station
Ave. Duration
5h 6m
Frequency
3 times a day
Estimated price
$40 - $60
Schedules at
amtrak.com
Book at
amtrak.com
Coach Seat
$40 - $60
Premium
$210 - $300
Flexi Coach Seat
$75 - $110
Business Seat
$75 - $110
Train from Buffalo Depew Station to Chicago Union Station
Ave. Duration
10h 30m
Frequency
4 times a day
Estimated price
$60 - $90
Schedules at
amtrak.com
Book at
amtrak.com
Coach Seat
$60 - $90
Premium
$250 - $350
Flexi Coach Seat
$120 - $180
Business Seat
$120 - $180
VIA Rail
Phone
+1 1 888 842-7245
Website
viarail.ca
Train from Toronto Union Station to Windsor
Ave. Duration
4h 18m
Frequency
4 times a day
Estimated price
$65 - $140
Website
VIA Rail
Escape
$40 - $55
Business
$90 - $110
Economy
$65 - $75
EconomyPlus
$100 - $140
Train from Toronto Union Station to Buffalo
Ave. Duration
4h 39m
Frequency
Once daily
Estimated price
$45 - $85
Website
VIA Rail
Escape
$25 - $40
Business
$70 - $85
Economy
$46 - $49
EconomyPlus
$60 - $85
GO Transit
Phone
+1 888-438-6646
Website
gotransit.com
Train from Toronto Union Station to London VIA
Ave. Duration
3h 58m
Frequency
5 times a week
Estimated price
$19 - $28
Website
GO Transit
Bus operators
Niagara Airbus
Rider Express
Phone
1-833-583-3636
Email
contact@riderexpress.ca
Website
riderexpress.ca
Bus from Toronto, ON to Windsor, ON
Ave. Duration
5h
Frequency
4 times a week
Estimated price
$35 - $70
Schedules at
riderexpress.ca
Book at
riderexpress.betterez.com
Adult
$35 - $55
Flixbus USA
Phone
(855) 626-8585
Website
flixbus.com
Bus from Detroit to Chicago
Ave. Duration
5h 10m
Frequency
5 times a week
Estimated price
$15 - $21
Schedules at
flixbus.com
Robert Q Airbus
Phone
(519) 679-2707
Email
courier@robertq.com
Website
robertq.com
Shuttle from London, ON - 105, Wharncliffe Road South, Manor Park to Detroit Airport
Ave. Duration
3h 30m
Frequency
On demand
Estimated price
$66
Schedules at
reservation.robertq.com
OurBus
Phone
+1 844-800-6828
Email
pr@ourbus.com
Website
ourbus.com
Bus from Ann Arbor, MI to Chicago, IL
Ave. Duration
3h 25m
Frequency
Once a week
Estimated price
$26 - $35
Book at
ourbus.com

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

The quickest flight from Billy Bishop Toronto City Airport to Chicago Midway Airport is the direct flight which takes 1h 50m.

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Toronto to Chicago (Station) bus services, operated by Flixbus USA, arrive at Chicago station.

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Chicago (Station) is 1h behind Toronto. It is currently 2:22 PM in Toronto and 1:22 PM in Chicago (Station).

Toronto to Chicago (Station) train services, operated by Amtrak, arrive at Chicago Union Station.

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Yes, the driving distance between Toronto to Chicago (Station) is 523 miles. It takes approximately 8h 47m to drive from Toronto to Chicago (Station).

Get driving directions

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

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Book your Toronto to Chicago (Station) train tickets online with Omio.

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There are 319+ hotels available in Chicago (Station). Prices start at $100 USD per night.

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The best way to get from Toronto to Billy Bishop Toronto City Airport is to car ferry which takes 2 min and costs $0 - $14.

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