There are 9 ways to get from Chicago to Midland by plane, bus, train, taxi, bus (Greyhound, Flixbus), 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.
Fly Chicago O'Hare International Airport to Toronto Pearson International Airport, bus
best- Fly from Chicago O'Hare International Airport (ORD) to Toronto Pearson International Airport (YYZ)plane ORD - YYZ
- Take the bus from Toronto Pearson Airport to Waubaushenebus
7h 33m$119–437Train, taxi
- Take the train from Chicago Union Station to Detroittrain
- Take the train from Windsor to Toronto Union Stationtrain
- Take the train from Union Station GO to Allandale Waterfront GOtrain Br
- Take the taxi from Allandale Waterfront GO to Midlandtaxi
14h 20m$430–803Bus
- Take the bus from Chicago Bus Station to Detroit Bus Stationbus
- Take the bus from Detroit Bus Station to Toronto Pearson Airportbus
- Take the bus from Toronto Pearson Airport to Port Severnbus
16h 42m$197–299Drive 878.6 km
- Drive from Chicago to Midlandcar 878.6 km
10h 43m$159–229Fly Chicago O'Hare International Airport to Buffalo Niagara International Airport, bus
- Fly from Chicago O'Hare International Airport (ORD) to Buffalo Niagara International Airport (BUF)plane ORD - BUF
- Take the bus from Buffalo Niagara International Airport to Toronto Pearson Airportbus
- Take the bus from Toronto Pearson Airport to Waubaushenebus
11h 44m$330–547Fly Chicago O'Hare International Airport to Toronto Island Airport, train, bus
- Fly from Chicago O'Hare International Airport (ORD) to Toronto Island Airport (YTZ)plane ORD - YTZ
- Take the train from Union Station GO to Allandale Waterfront GOtrain
- Take the bus from Barrie, Georgian College to Huronia Mallbus
10h 15m$312–1,866Fly Chicago Midway International Airport to Buffalo Niagara International Airport, bus
- Fly from Chicago Midway International Airport (MDW) to Buffalo Niagara International Airport (BUF)plane MDW - BUF
- Take the bus from Buffalo Niagara International Airport to Toronto Pearson Airportbus
- Take the bus from Toronto Pearson Airport to Waubaushenebus
11h 26m$340–567Bus, drive
- Take the bus from Chicago Union Station to Detroitbus
- Take the bus from Detroit Bus Station to Scarborough Centrebus
- Drive from Seneca College Stop # 1706 to Midlandcar
18h 28mTrain, bus
- Take the train from Chicago Union Station to Buffalo Depew Stationtrain
- Take the train from Buffalo to Toronto Union Stationtrain
- Take the bus from Toronto to Waubaushenebus
19h 38m$511–951
Chicago O'Hare International Airport (ORD) to Toronto Pearson International Airport (YYZ) flights
Comparing Your Travel Options
The cheapest way to get from Chicago to Midland is to drive which costs $150 - $230 and takes 10h 43m.
The fastest way to get from Chicago to Midland is to fly and bus which takes 7h 33m and costs $110 - $440.
No, there is no direct bus from Chicago station to Midland. However, there are services departing from Chicago Bus Station and arriving at Port Severn via Detroit Bus Station and Toronto Pearson Airport. The journey, including transfers, takes approximately 16h 42m.
The distance between Chicago and Midland is 889 km. The road distance is 878.6 km.
The best way to get from Chicago to Midland without a car is to bus which takes 16h 42m and costs $190 - $300.
It takes approximately 7h 33m to get from Chicago to Midland, including transfers.
Chicago to Midland bus services, operated by Greyhound USA, depart from Chicago Bus Station.
Chicago to Midland bus services, operated by Greyhound USA, arrive at Detroit Bus Station.
Midland is 1h ahead of Chicago. It is currently 10:13 PM in Chicago and 11:13 PM in Midland.
Yes, the driving distance between Chicago to Midland is 879 km. It takes approximately 10h 43m to drive from Chicago to Midland.
What companies run services between Chicago, IL, USA and Midland, ON, Canada?
You can take a bus from Chicago Bus Station to Midland via Detroit Bus Station, Toronto Pearson Airport, and Port Severn in around 16h 42m.
- Website
- aircanada.com
Flights from Chicago O'Hare International Airport to Toronto Pearson International Airport
- Ave. Duration
- 1h 46m
- When
- Every day
- Estimated price
- $55–350
Flights from Chicago O'Hare International Airport to Buffalo Niagara International Airport
- Ave. Duration
- 1h 47m
- When
- Every day
- Estimated price
- $100–650
Flights from Chicago O'Hare International Airport to Toronto Island Airport
- Ave. Duration
- 1h 47m
- When
- Every day
- Estimated price
- $60–370
- Website
- united.com
Flights from Chicago O'Hare International Airport to Toronto Pearson International Airport
- Ave. Duration
- 1h 46m
- When
- Every day
- Estimated price
- $55–350
Flights from Chicago O'Hare International Airport to Buffalo Niagara International Airport
- Ave. Duration
- 1h 47m
- When
- Every day
- Estimated price
- $100–650
Flights from Chicago O'Hare International Airport to Toronto Island Airport
- Ave. Duration
- 1h 47m
- When
- Every day
- Estimated price
- $60–370
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Toronto Pearson International Airport
- Ave. Duration
- 1h 52m
- When
- Every day
- Estimated price
- $55–350
Flights from Chicago O'Hare International Airport to Buffalo Niagara International Airport
- Ave. Duration
- 1h 44m
- When
- Every day
- Estimated price
- $100–650
- Website
- flyporter.com
Flights from Chicago O'Hare International Airport to Toronto Pearson International Airport
- Ave. Duration
- 1h 52m
- When
- Every day
- Estimated price
- $55–350
Flights from Chicago O'Hare International Airport to Toronto Island Airport
- Ave. Duration
- 1h 45m
- When
- Every day
- Estimated price
- $240–1,100
- Website
- southwest.com
Flights from Chicago Midway International Airport to Buffalo Niagara International Airport
- Ave. Duration
- 1h 34m
- When
- Every day
- Estimated price
- $170–1,100
- Website
- delta.com
Flights from Chicago O'Hare International Airport to Buffalo Niagara International Airport via Detroit
- Ave. Duration
- 3h 36m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $100–650
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Detroit
- Ave. Duration
- 5h 20m
- Frequency
- 3 times a day
- Estimated price
- $210–340
- Website
- Amtrak
Train from Chicago Union Station to Buffalo Depew Station
- Ave. Duration
- 10h 23m
- Frequency
- Twice daily
- Estimated price
- $400–650
- Website
- Amtrak
- Phone
- +1 888 842-7245
- Website
- VIA Rail
Train from Windsor to Toronto Union Station
- Ave. Duration
- 4h 10m
- Frequency
- 4 times a day
- Estimated price
- $80–300
- Website
- VIA Rail
- Escape
- $80–210
- Business
- $130–280
- Business Plus
- $140–300
- Economy
- $90–220
- Economy Plus
- $100–230
Train from Buffalo to Toronto Union Station
- Ave. Duration
- 4h 24m
- Frequency
- Once daily
- Estimated price
- $40–240
- Website
- VIA Rail
- Escape
- $40–130
- Business
- $85–230
- Business Plus
- $100–240
- Economy
- $45–140
- Economy Plus
- $50–150
- Phone
- +1 888 438 6646
- Website
- GO Transit
Train from Union Station GO to Allandale Waterfront GO
- Ave. Duration
- 1h 48m
- Frequency
- Every 4 hours
- Estimated price
- $12–16
- Website
- GO Transit
Train from Union Station GO to Allandale Waterfront GO
- Ave. Duration
- 1h 48m
- Frequency
- Every 4 hours
- Estimated price
- $12–16
- Website
- GO Transit
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Toronto Pearson Airport to Waubaushene
- Ave. Duration
- 1h 55m
- Frequency
- 5 times a week
- Estimated price
- $20–30
- Schedules at
- Flixbus USA
Bus from Chicago Bus Station to Detroit Bus Station
- Ave. Duration
- 7h 25m
- Frequency
- Twice daily
- Estimated price
- $65–100
- Schedules at
- Flixbus USA
Bus from Detroit Bus Station to Toronto Pearson Airport
- Ave. Duration
- 6h 15m
- Frequency
- Twice daily
- Estimated price
- $50–80
- Schedules at
- Flixbus USA
Bus from Toronto Pearson Airport to Port Severn
- Ave. Duration
- 2h
- Frequency
- 5 times a week
- Estimated price
- $21–35
- Schedules at
- Flixbus USA
Bus from Buffalo Niagara International Airport to Toronto Pearson Airport
- Ave. Duration
- 4h 10m
- Frequency
- 5 times a week
- Estimated price
- $26–40
- Schedules at
- Flixbus USA
Bus from Toronto Pearson Airport to Waubaushene
- Ave. Duration
- 1h 55m
- Frequency
- 5 times a week
- Estimated price
- $20–30
- Schedules at
- Flixbus USA
Bus from Buffalo Niagara International Airport to Toronto Pearson Airport
- Ave. Duration
- 4h 10m
- Frequency
- 5 times a week
- Estimated price
- $26–40
- Schedules at
- Flixbus USA
Bus from Toronto Pearson Airport to Waubaushene
- Ave. Duration
- 1h 55m
- Frequency
- 5 times a week
- Estimated price
- $20–30
- Schedules at
- Flixbus USA
Bus from Detroit Bus Station to Scarborough Centre
- Ave. Duration
- 7h 5m
- Frequency
- 4 times a day
- Estimated price
- $60–90
- Schedules at
- Flixbus USA
Bus from Toronto to Waubaushene
- Ave. Duration
- 2h 35m
- Frequency
- 5 times a week
- Estimated price
- $23–35
- Schedules at
- Flixbus USA
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Chicago Bus Station to Detroit Bus Station
- Ave. Duration
- 6h 5m
- Frequency
- 3 times a day
- Estimated price
- $70–110
- Website
- Greyhound
- Phone
- +1 800 263 3199
- [email protected]
- Website
- Simcoe County Transit
Bus from Barrie, Georgian College to Huronia Mall
- Ave. Duration
- 55 min
- Frequency
- Every 3 hours
- Estimated price
- $4–7
- Website
- Simcoe County Transit
- Passenger
- $4–7
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Bus from Chicago Union Station to Detroit
- Ave. Duration
- 5h 20m
- Frequency
- Twice a week
- Website
- Amtrak
- Ave. Duration
- 47 min
- Estimated price
- $120–150
Barrie Taxi
- Phone
- +1 705 721 7777
- Website
- barrietaxi.com
Deluxe Taxi
- Phone
- +1 705 728 4444
- Website
- deluxtaxi.ca
Innisfil Taxi
- Phone
- +1 705 431 1114
- Website
- innisfiltaxi.com
Want to know more about travelling around Canada
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Booking & Getting There
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