There are 9 ways to get from Oakville to Milwaukee by train (Amtrak), bus (Flixbus), car, plane, train, or bus
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Train via Detroit
best- Take the train from Oakville to Windsortrain
- Take the train from Detroit to Chicago Union Stationtrain
- Take the train from Chicago Union Station to Milwaukeetrain
12h 42m$250–516Fly Toronto Pearson International Airport to Chicago O'Hare International Airport, bus
cheapest- Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane YYZ - ORD
- Take the bus from Chicago to Milwaukee Intermodal Stationbus
7h 56m$61–283Bus (Flixbus)
- Take the bus from Mississauga to Detroit Bus Stationbus FlixBus N2706
- Take the bus from Detroit Bus Station to Milwaukee Intermodal Stationbus FlixBus 2550
16h 41m$99–150Drive 575.5 mi
- Drive from Oakville to Milwaukeecar 575.5 mi
9h 54m$119–171Fly Toronto Pearson International Airport to General Mitchell International Airport
- Fly from Toronto Pearson International Airport (YYZ) to General Mitchell International Airport (MKE)plane YYZ - MKE
7h 49m$83–479Train
- Take the train from Oakville to Buffalotrain
- Take the train from Buffalo Depew Station to Chicago Union Stationtrain
- Take the train from Chicago Union Station to Milwaukeetrain
17h 55m$350–688Fly Toronto Island Airport to General Mitchell International Airport
- Fly from Toronto Island Airport (YTZ) to General Mitchell International Airport (MKE)plane YTZ - MKE
7h 40m$94–523Train to Detroit, fly to General Mitchell International Airport
- Take the train from Oakville to Windsortrain
- Fly from Detroit (DTW) to General Mitchell International Airport (MKE)plane DTW - MKE
8h 18m$1,010–1,256Fly Toronto Island Airport to Chicago O'Hare International Airport, bus
- Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane YTZ - ORD
- Take the bus from Chicago to Milwaukee Intermodal Stationbus
7h 37m$222–1,347
Oakville to Milwaukee by train and car
Comparing Your Travel Options
The cheapest way to get from Oakville to Milwaukee is to bus which costs $95 - $150 and takes 16h 41m.
The fastest way to get from Oakville to Milwaukee is to fly and bus which takes 7h 37m and costs $220 - $1,400.
No, there is no direct bus from Oakville to Milwaukee station. However, there are services departing from Oakville GO Bus and arriving at Milwaukee Intermodal Station via Mississauga and Detroit Bus Station. The journey, including transfers, takes approximately 16h 41m.
No, there is no direct train from Oakville to Milwaukee. However, there are services departing from Oakville and arriving at Milwaukee via Detroit and Chicago Union Station. The journey, including transfers, takes approximately 12h 42m.
The distance between Oakville and Milwaukee is 576 miles. The road distance is 578.8 miles.
The best way to get from Oakville to Milwaukee without a car is to bus which takes 16h 41m and costs $95 - $150.
It takes approximately 12h 42m to get from Oakville to Milwaukee, including transfers.
Oakville to Milwaukee bus services, operated by Flixbus USA, depart from Mississauga station.
Oakville to Milwaukee train services, operated by VIA Rail, depart from Oakville station.
The best way to get from Oakville to Milwaukee is to train via Detroit which takes 12h 42m and costs $250 - $550. Alternatively, you can bus, which costs $95 - $150 and takes 16h 41m, you could also fly, which costs $80 - $480 and takes 7h 49m.
What companies run services between Oakville, ON, Canada and Milwaukee, WI, USA?
You can take a train from Oakville to Milwaukee via Windsor, Detroit, and Chicago Union Station in around 12h 42m. Alternatively, you can take a bus from Oakville GO Bus to Milwaukee Intermodal Station via Square One, Mississauga, and Detroit Bus Station in around 16h 41m.
- Website
- united.com
Flights from Toronto Pearson International Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 4h 53m
- When
- Every day
- Estimated price
- $80–480
Flights from Toronto Pearson International Airport to General Mitchell International Airport via Newark
- Ave. Duration
- 6h
- When
- Wednesday, Thursday, Monday, Tuesday, Friday, and Sunday
- Estimated price
- $120–650
Flights from Toronto Island Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 5h
- When
- Every day
- Estimated price
- $85–1,100
Flights from Toronto Pearson International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 8m
- When
- Every day
- Estimated price
- $40–250
Flights from Toronto Island Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 15m
- When
- Every day
- Estimated price
- $40–260
- Website
- aa.com
Flights from Toronto Pearson International Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 5h 32m
- When
- Every day
- Estimated price
- $80–480
Flights from Toronto Pearson International Airport to General Mitchell International Airport via Philadelphia
- Ave. Duration
- 5h 26m
- When
- Every day
- Estimated price
- $120–600
Flights from Toronto Pearson International Airport to General Mitchell International Airport via Reagan Washington
- Ave. Duration
- 7h 41m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $110–600
Flights from Toronto Island Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 4h 27m
- When
- Every day
- Estimated price
- $260–1,100
Flights from Toronto Pearson International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 23m
- When
- Every day
- Estimated price
- $40–250
- Website
- aircanada.com
Flights from Toronto Pearson International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 8m
- When
- Every day
- Estimated price
- $40–250
Flights from Toronto Island Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 15m
- When
- Every day
- Estimated price
- $40–260
- Website
- delta.com
Flights from Toronto Pearson International Airport to General Mitchell International Airport via Detroit
- Ave. Duration
- 4h 18m
- When
- Every day
- Estimated price
- $75–470
Flights from Toronto Pearson International Airport to General Mitchell International Airport via Minneapolis
- Ave. Duration
- 5h 42m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $110–600
Flights from Toronto Island Airport to General Mitchell International Airport via New York La Guardia
- Ave. Duration
- 6h 5m
- When
- Monday to Friday
- Estimated price
- $130–650
Flights from Toronto Island Airport to General Mitchell International Airport via Boston
- Ave. Duration
- 6h 13m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $140–700
Flights from Detroit to General Mitchell International Airport
- Ave. Duration
- 1h 22m
- When
- Every day
- Estimated price
- $95–700
- Website
- flyporter.com
Flights from Toronto Pearson International Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 5h 16m
- When
- Every day
- Estimated price
- $80–480
Flights from Toronto Island Airport to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 5h 57m
- When
- Every day
- Estimated price
- $260–1,100
Flights from Toronto Pearson International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 23m
- When
- Every day
- Estimated price
- $40–250
Flights from Toronto Island Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 5m
- When
- Every day
- Estimated price
- $170–800
- Website
- southwest.com
Flights from Detroit to General Mitchell International Airport via Chicago Midway
- Ave. Duration
- 3h 32m
- When
- Every day
- Estimated price
- $100–700
- Phone
- +1 888 842-7245
- Website
- VIA Rail
Train from Oakville to Windsor
- Ave. Duration
- 3h 53m
- Frequency
- 4 times a day
- Estimated price
- $50–200
- Website
- VIA Rail
- Escape
- $50–140
- Business
- $85–190
- Business Plus
- $95–200
- Economy
- $60–140
- Economy Plus
- $65–150
Train from Oakville to Buffalo
- Ave. Duration
- 3h 53m
- Frequency
- Once daily
- Estimated price
- $25–170
- Website
- VIA Rail
- Escape
- $25–80
- Business
- $55–160
- Business Plus
- $65–170
- Economy
- $28–85
- Economy Plus
- $30–95
Train from Oakville to Windsor
- Ave. Duration
- 3h 53m
- Frequency
- 4 times a day
- Estimated price
- $50–200
- Website
- VIA Rail
- Escape
- $50–140
- Business
- $85–190
- Business Plus
- $95–200
- Economy
- $60–140
- Economy Plus
- $65–150
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Detroit to Chicago Union Station
- Ave. Duration
- 5h 6m
- Frequency
- 3 times a day
- Estimated price
- $150–240
- Website
- Amtrak
Train from Chicago Union Station to Milwaukee
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $45–75
- Website
- Amtrak
Train from Buffalo Depew Station to Chicago Union Station
- Ave. Duration
- 10h 33m
- Frequency
- Twice daily
- Estimated price
- $280–450
- Website
- Amtrak
Train from Chicago Union Station to Milwaukee
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $45–75
- Website
- Amtrak
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Mississauga to Detroit Bus Station
- Ave. Duration
- 6h 5m
- Frequency
- 5 times a week
- Estimated price
- $35–55
- Schedules at
- Flixbus USA
Bus from Detroit Bus Station to Milwaukee Intermodal Station
- Ave. Duration
- 7h 40m
- Frequency
- 4 times a week
- Estimated price
- $60–90
- Schedules at
- Flixbus USA
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Chicago to Milwaukee Intermodal Station
- Ave. Duration
- 1h 20m
- Frequency
- Once daily
- Estimated price
- $14–22
- Website
- Greyhound
Bus from Chicago to Milwaukee Intermodal Station
- Ave. Duration
- 1h 20m
- Frequency
- Once daily
- Estimated price
- $14–22
- Website
- Greyhound
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Booking & Getting There
Oakville to Milwaukee bus services, operated by Flixbus USA, arrive at Detroit Bus Station.
Milwaukee is 1h behind Oakville. It is currently 7:58 PM in Oakville and 6:58 PM in Milwaukee.
Oakville to Milwaukee train services, operated by VIA Rail, arrive at Windsor station.
Yes, the driving distance between Oakville to Milwaukee is 579 miles. It takes approximately 9h 54m to drive from Oakville to Milwaukee.
Book your Oakville to Milwaukee train tickets online with Omio.
There are 322+ hotels available in Milwaukee.










