There are 10 ways to get from Alliston to Chicago by train, plane, train (Amtrak), bus, car, or shuttle
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Train to Toronto Pearson International Airport, fly to Chicago O'Hare International Airport
best- Take the train from Bradford GO to Toronto Union Stationtrain
- Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane YYZ - ORD
8h 19m$194–491Train to Toronto Pearson International Airport, fly to Chicago Midway International Airport
cheapest- Take the train from Bradford GO to Toronto Union Stationtrain
- Fly from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW)plane YYZ - MDW
9h 48m$69–371Train via Detroit
- Take the train from Bradford GO to Toronto Union Stationtrain Br
- Take the train from Toronto Union Station to Windsortrain
- Take the train from Detroit to Chicago Union Stationtrain
14h 41m$88–209Train, bus
- Take the train from Bradford GO to Toronto Union Stationtrain Br
- Take the bus from Toronto to Detroit Bus Stationbus
- Take the bus from Detroit Bus Station to Chicago Bus Stationbus
18h 3m$77–146Drive 502.6 mi
- Drive from Alliston to Chicagocar 502.6 mi
9h 37m$115–167Train to Toronto Island Airport, fly to Chicago Midway International Airport
- Take the train from Bradford GO to Toronto Union Stationtrain
- Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane YTZ - MDW
8h 12m$127–495Train to Toronto Island Airport, fly to Chicago O'Hare International Airport
- Take the train from Bradford GO to Toronto Union Stationtrain
- Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane YTZ - ORD
8h 22m$207–495Train, shuttle to Buffalo Niagara International Airport, fly to Chicago O'Hare International Airport
- Take the train from Bradford GO to Toronto Union Stationtrain
- Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airport
- Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane BUF - ORD
9h 54m$184–641Train, shuttle to Buffalo Niagara International Airport, fly to Chicago Midway International Airport
- Take the train from Bradford GO to Toronto Union Stationtrain
- Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airport
- Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane BUF - MDW
9h 48m$224–891Train
- Take the train from Bradford GO to Toronto Union Stationtrain Br
- Take the train from Toronto Union Station to Buffalotrain
- Take the train from Buffalo Depew Station to Chicago Union Stationtrain
19h 42m$90–296
Alliston to Chicago by bus, train, and car
Questions & Answers
The cheapest way to get from Alliston to Chicago is to train and bus which costs $75 - $150 and takes 18h 3m.
The fastest way to get from Alliston to Chicago is to train and fly which takes 8h 12m and costs $120 - $500.
The distance between Alliston and Chicago is 536 miles. The road distance is 505.5 miles.
The best way to get from Alliston to Chicago without a car is to train and bus which takes 18h 3m and costs $75 - $150.
It takes approximately 8h 19m to get from Alliston to Chicago, including transfers.
Chicago is 1h behind Alliston. It is currently 11:32 AM in Alliston and 10:32 AM in Chicago.
Yes, the driving distance between Alliston to Chicago is 506 miles. It takes approximately 9h 37m to drive from Alliston to Chicago.
There are 1251+ hotels available in Chicago.
What companies run services between Alliston, ON, Canada and Chicago, IL, USA?
You can take a bus from Wellington St at Centre St S to Chicago Union Station via Bradford GO Station, Bradford GO, Toronto Union Station, Windsor, and Detroit in around 14h 41m.
- Website
- aircanada.com
Flights from Toronto Pearson International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 5m
- When
- Every day
- Estimated price
- $35–230
Flights from Toronto Island Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 55m
- When
- Monday to Friday
- Estimated price
- $35–230
Flights from Toronto Island Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 4h 47m
- When
- Monday and Saturday
- Estimated price
- $55–290
Flights from Buffalo Niagara International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 7m
- When
- Every day
- Estimated price
- $80–500
- Website
- united.com
Flights from Toronto Pearson International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 5m
- When
- Every day
- Estimated price
- $35–230
Flights from Toronto Island Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 55m
- When
- Monday to Friday
- Estimated price
- $35–230
Flights from Toronto Island Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 4h 47m
- When
- Monday and Saturday
- Estimated price
- $55–290
Flights from Buffalo Niagara International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 7m
- When
- Every day
- Estimated price
- $80–500
- Website
- aa.com
Flights from Toronto Pearson International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 2m
- When
- Every day
- Estimated price
- $35–230
Flights from Buffalo Niagara International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 11m
- When
- Every day
- Estimated price
- $80–500
- Website
- southwest.com
Flights from Toronto Pearson International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 3h 30m
- When
- Tuesday and Wednesday
- Estimated price
- $55–350
Flights from Toronto Pearson International Airport to Chicago Midway International Airport via Cleveland
- Ave. Duration
- 4h 20m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $60–360
Flights from Toronto Pearson International Airport to Chicago Midway International Airport via Pittsburgh
- Ave. Duration
- 4h 30m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $65–390
Flights from Toronto Pearson International Airport to Chicago Midway International Airport via Reagan Washington
- Ave. Duration
- 4h 35m
- When
- Tuesday and Wednesday
- Estimated price
- $85–450
Flights from Buffalo Niagara International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h
- When
- Every day
- Estimated price
- $120–750
Flights from Buffalo Niagara International Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 43m
- When
- Monday to Thursday
- Estimated price
- $170–950
- Website
- flyporter.com
Flights from Toronto Pearson International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 2m
- When
- Every day
- Estimated price
- $35–230
Flights from Toronto Island Airport to Chicago Midway International Airport
- Ave. Duration
- 1h 50m
- When
- Every day
- Estimated price
- $110–410
- Website
- delta.com
Flights from Toronto Pearson International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 4h 39m
- When
- Every day
- Estimated price
- $55–350
Flights from Buffalo Niagara International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 3h 50m
- When
- Every day
- Estimated price
- $80–500
Flights from Buffalo Niagara International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 3h 49m
- When
- Every day
- Estimated price
- $120–750
- Phone
- +1 888-438-6646
- Website
- gotransit.com
Train from Bradford GO to Toronto Union Station
- Ave. Duration
- 1h 17m
- Frequency
- Every 3 hours
- Estimated price
- $9–12
- Website
- https://www.gotransit.com/
- Website
- https://www.gotransit.com/en/see-schedules
- Passenger
- $9–12
- Phone
- +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
- $35–100
- Website
- https://www.viarail.ca/en
- Economy Adult - same day booking
- $40–100
- Economy Adult - Advanced Booking
- $40–80
- Economy Escape Advanced Booking - Adult
- $35–55
Train from Toronto Union Station to Buffalo
- Ave. Duration
- 4h 6m
- Frequency
- Once daily
- Estimated price
- $23–90
- Website
- https://www.viarail.ca/en
- Economy Adult - same day booking
- $26–90
- Economy Adult - Advanced Booking
- $26–70
- Economy Escape Advanced Booking - Adult
- $23–40
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Detroit to Chicago Union Station
- Ave. Duration
- 5h 6m
- Frequency
- 3 times a day
- Estimated price
- $40–90
- Website
- https://www.amtrak.com/home.html
Train from Buffalo Depew Station to Chicago Union Station
- Ave. Duration
- 10h 33m
- Frequency
- Twice daily
- Estimated price
- $55–190
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Toronto to Detroit Bus Station
- Ave. Duration
- 6h 55m
- Frequency
- 4 times a day
- Estimated price
- $35–60
- Schedules at
- flixbus.com
Bus from Detroit Bus Station to Chicago Bus Station
- Ave. Duration
- 7h 50m
- Frequency
- Twice daily
- Estimated price
- $35–70
- Schedules at
- flixbus.com
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Detroit Bus Station to Chicago Bus Station
- Ave. Duration
- 6h 5m
- Frequency
- 3 times a day
- Estimated price
- $30–60
- Website
- https://www.greyhound.com/
- Phone
- 905-374-8111
- airsales@niagaraairbus.com
- Website
- niagaraairbus.com
Shuttle from Pearson International Airport Terminal 1 to Buffalo Airport
- Ave. Duration
- 2h
- Frequency
- On demand
- Estimated price
- $90–120
- Website
- https://www.niagaraairbus.com
- Schedules at
- https://www.niagaraairbus.com
- Book at
- https://www.niagaraairbus.com
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