There are 9 ways to get from Ann Arbor to Winnetka by train (Amtrak), bus (Greyhound, Flixbus), car, plane, bus (Amtrak), bus, or train
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Train (Amtrak)
best- Take the train from Ann Arbor Amtrak Station to Chicago Union Stationtrain Wolverine
5h 31m$87–167Bus
cheapest- Take the bus from Ann Arbor to Chicago Bus Stationbus Greyhound US0160
6h 46m$46–81Drive 258.2 mi
- Drive from Ann Arbor to Winnetkacar 258.2 mi
4h 29m$48–69Drive to Capital Region International Airport, fly to Chicago O'Hare International Airport
- Drive from Ann Arbor to Lansing-Airport-LANcar
- Fly from Capital Region International Airport (LAN) to Chicago O'Hare International Airport (ORD)plane LAN - ORD
4h 22m$59–319Bus via Rogers & Paulina (Amtrak)
- Take the bus from Ann Arbor Amtrak Station to Chicago Union Stationbus Amtrak Thruway Connecting Service
6h 47m$91–125Bus to Detroit, fly to Chicago Midway International Airport, train
- Take the bus from Ann Arbor- Blake Transit Ctr., MI to Detroit Metro Airportbus
- Fly from Detroit (DTW) to Chicago Midway International Airport (MDW)plane DTW - MDW
- Take the train from Chicago OTC to Winnetkatrain
4h 56m$143–487Bus to Detroit, fly to Chicago O'Hare International Airport
- Take the bus from Ann Arbor- Blake Transit Ctr., MI to Detroit Metro Airportbus
- Fly from Detroit (DTW) to Chicago O'Hare International Airport (ORD)plane DTW - ORD
5h 9m$163–678Bus to Detroit, fly to South Bend, train
- Take the bus from Ann Arbor- Blake Transit Ctr., MI to Detroit Metro Airportbus
- Fly from Detroit (DTW) to South Bend (SBN)plane DTW - SBN
- Take the train from South Bend Airport to Millennium Stationtrain
7h 8m$97–590Bus to Detroit, fly to General Mitchell International Airport, train
- Take the bus from Ann Arbor- Blake Transit Ctr., MI to Detroit Metro Airportbus
- Fly from Detroit (DTW) to General Mitchell International Airport (MKE)plane DTW - MKE
- Take the train from Milwaukee to Glenview Amtrak Stationtrain
6h 53m$632–1,079
Ann Arbor to Winnetka by train, foot, and bus (Amtrak)
Questions & Answers
The cheapest way to get from Ann Arbor to Winnetka is to bus which costs $45 - $85 and takes 6h 46m.
The fastest way to get from Ann Arbor to Winnetka is to drive and fly which takes 4h 22m and costs $55 - $320.
No, there is no direct bus from Ann Arbor to Winnetka. However, there are services departing from Ann Arbor and arriving at Washington & Canal via Desplaines & Harrison Terminal. The journey, including transfers, takes approximately 6h 46m.
No, there is no direct train from Ann Arbor station to Winnetka. However, there are services departing from Ann Arbor Amtrak Station and arriving at Winnetka via Chicago OTC. The journey, including transfers, takes approximately 5h 31m.
The distance between Ann Arbor and Winnetka is 261 miles. The road distance is 259.7 miles.
The best way to get from Ann Arbor to Winnetka without a car is to train which takes 5h 31m and costs $85 - $170.
It takes approximately 5h 31m to get from Ann Arbor to Winnetka, including transfers.
Ann Arbor to Winnetka bus services, operated by Greyhound USA, depart from Ann Arbor station.
Ann Arbor to Winnetka train services, operated by Amtrak, depart from Ann Arbor Amtrak Station.
The best way to get from Ann Arbor to Winnetka is to train which takes 5h 31m and costs $85 - $170. Alternatively, you can bus, which costs $45 - $85 and takes 6h 46m.
What companies run services between Ann Arbor, MI, USA and Winnetka, IL, USA?
Amtrak operates a train from Ann Arbor Amtrak Station to Chicago Union Station 3 times a day. Tickets cost $75–160 and the journey takes 4h 18m. Alternatively, Greyhound USA operates a bus from Ann Arbor to Chicago Bus Station 3 times a day. Tickets cost $35–75 and the journey takes 5h. Flixbus USA also services this route 5 times a week.
- Website
- delta.com
Flights from Capital Region International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 3h 19m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $50–310
Flights from Detroit to Chicago Midway International Airport
- Ave. Duration
- 1h 19m
- When
- Every day
- Estimated price
- $50–330
Flights from Detroit to Chicago O'Hare International Airport
- Ave. Duration
- 1h 29m
- When
- Every day
- Estimated price
- $40–280
Flights from Detroit to South Bend
- Ave. Duration
- 1h 5m
- When
- Every day
- Estimated price
- $70–550
Flights from Detroit to General Mitchell International Airport
- Ave. Duration
- 1h 17m
- When
- Every day
- Estimated price
- $70–490
- Website
- aa.com
Flights from Capital Region International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 19m
- When
- Every day
- Estimated price
- $40–290
Flights from Detroit to Chicago O'Hare International Airport
- Ave. Duration
- 1h 42m
- When
- Every day
- Estimated price
- $40–280
Flights from Detroit to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 3h 23m
- When
- Every day
- Estimated price
- $80–550
- Website
- southwest.com
Flights from Detroit to Chicago Midway International Airport
- Ave. Duration
- 1h 11m
- When
- Every day
- Estimated price
- $50–330
Flights from Detroit to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 3h 5m
- When
- Monday, Thursday, and Friday
- Estimated price
- $80–550
- Website
- united.com
Flights from Capital Region International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 20m
- When
- Every day
- Estimated price
- $40–290
Flights from Detroit to Chicago O'Hare International Airport
- Ave. Duration
- 1h 31m
- When
- Every day
- Estimated price
- $40–280
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Ann Arbor Amtrak Station to Chicago Union Station
- Ave. Duration
- 4h 18m
- Frequency
- 3 times a day
- Estimated price
- $75–160
- Website
- https://www.amtrak.com/home.html
Train from Milwaukee to Glenview Amtrak Station
- Ave. Duration
- 1h
- Frequency
- Every 4 hours
- Estimated price
- $22–45
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 312-696-3872
- Website
- metra.com
Train from Chicago OTC to Winnetka
- Ave. Duration
- 38 min
- Frequency
- Hourly
- Estimated price
- $4–5
- Website
- https://metra.com
- Adult
- $4–5
- Phone
- +1 219-926-5744
- Website
- mysouthshoreline.com
Train from South Bend Airport to Millennium Station
- Ave. Duration
- 2h 4m
- Frequency
- Every 2 hours
- Estimated price
- $13–15
- Schedules at
- mysouthshoreline.com
- Adults 14-64
- $13–15
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- greyhound.com
Bus from Ann Arbor to Chicago Bus Station
- Ave. Duration
- 5h
- Frequency
- 3 times a day
- Estimated price
- $35–75
- Website
- https://www.greyhound.com/
- Phone
- +1 (855) 626-8585
- Website
- https://www.flixbus.com
Bus from Ann Arbor to Chicago Bus Station
- Ave. Duration
- 3h 55m
- Frequency
- 5 times a week
- Estimated price
- $35–65
- Schedules at
- flixbus.com
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Bus from Ann Arbor Amtrak Station to Chicago Union Station
- Ave. Duration
- 4h 39m
- Frequency
- Once a week
- Estimated price
- $85–120
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 517-333-0400
- [email protected]
- Website
- michiganflyer.com
Bus from Ann Arbor- Blake Transit Ctr., MI to Detroit Metro Airport
- Ave. Duration
- 40 min
- Frequency
- Hourly
- Estimated price
- $7–15
- Website
- https://www.michiganflyer.com/
- Child 2-16
- $7–9
- Adult
- $10–15
Bus from Ann Arbor- Blake Transit Ctr., MI to Detroit Metro Airport
- Ave. Duration
- 40 min
- Frequency
- Hourly
- Estimated price
- $7–15
- Website
- https://www.michiganflyer.com/
- Child 2-16
- $7–9
- Adult
- $10–15
Bus from Ann Arbor- Blake Transit Ctr., MI to Detroit Metro Airport
- Ave. Duration
- 40 min
- Frequency
- Hourly
- Estimated price
- $7–15
- Website
- https://www.michiganflyer.com/
- Child 2-16
- $7–9
- Adult
- $10–15
Bus from Ann Arbor- Blake Transit Ctr., MI to Detroit Metro Airport
- Ave. Duration
- 40 min
- Frequency
- Hourly
- Estimated price
- $7–15
- Website
- https://www.michiganflyer.com/
- Child 2-16
- $7–9
- Adult
- $10–15
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More Questions & Answers
Ann Arbor to Winnetka bus services, operated by Greyhound USA, arrive at Chicago Bus Station.
Winnetka is 1h behind Ann Arbor. It is currently 11:44 AM in Ann Arbor and 10:44 AM in Winnetka.
Ann Arbor to Winnetka train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Ann Arbor to Winnetka is 260 miles. It takes approximately 4h 29m to drive from Ann Arbor to Winnetka.
There are 176+ hotels available in Winnetka.








