There are 8 ways to get from Ann Arbor to Winnetka by train (Amtrak), bus (Greyhound, Flixbus), car, bus, plane, 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 StationWolverine
5h 25m$47–132Bus
cheapest- Take the bus from Ann Arbor to Chicago Bus StationGreyhound US0160
7h 30m$39–88Drive 258.1 mi
- Drive from Ann Arbor to Winnetka258.1 mi
4h 26m$48–68Bus to Detroit, fly to Chicago Midway International Airport, train
- Take the bus from Ann Arbor- Blake Transit Ctr., MI to Detroit Metro Airport
- Fly from Detroit (DTW) to Chicago Midway International Airport (MDW)DTW - MDW
- Take the train from Chicago OTC to Winnetka
4h 57m$56–358Drive to Capital Region International Airport, fly to Chicago O'Hare International Airport
- Drive from Ann Arbor to Capital Region International Airport (LAN)
- Fly from Capital Region International Airport (LAN) to Chicago O'Hare International Airport (ORD)LAN - ORD
4h 31m$55–343Bus to Detroit, fly to Chicago O'Hare International Airport
- Take the bus from Ann Arbor- Blake Transit Ctr., MI to Detroit Metro Airport
- Fly from Detroit (DTW) to Chicago O'Hare International Airport (ORD)DTW - ORD
5h 12m$119–372Bus to Detroit, fly to South Bend, train
- Take the bus from Ann Arbor- Blake Transit Ctr., MI to Detroit Metro Airport
- Fly from Detroit (DTW) to South Bend (SBN)DTW - SBN
- Take the train from South Bend Airport to Millennium Station
7h 9m$70–391Bus to Detroit, fly to General Mitchell International Airport, train
- Take the bus from Ann Arbor- Blake Transit Ctr., MI to Detroit Metro Airport
- Fly from Detroit (DTW) to General Mitchell International Airport (MKE)DTW - MKE
- Take the train from Milwaukee to Glenview Amtrak Station
6h 52m$221–685
Ann Arbor to Winnetka by train and foot (Amtrak)
Questions & Answers
The cheapest way to get from Ann Arbor to Winnetka is to bus which costs $35 - $90 and takes 7h 30m.
The fastest way to get from Ann Arbor to Winnetka is to drive which takes 4h 26m and costs $45 - $70.
No, there is no direct bus from Ann Arbor to Winnetka. However, there are services departing from Ann Arbor and arriving at Green Bay Rd & Pine St via Jefferson & Harrison, Michigan & Hubbard and Howard CTA Station. The journey, including transfers, takes approximately 7h 30m.
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 25m.
The distance between Ann Arbor and Winnetka is 261 miles. The road distance is 259.6 miles.
The best way to get from Ann Arbor to Winnetka without a car is to train which takes 5h 25m and costs $45 - $140.
It takes approximately 5h 25m 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 25m and costs $45 - $140. Alternatively, you can bus, which costs $35 - $90 and takes 7h 30m.
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 $45–130 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 $30–60 and the journey takes 5h 5m. Flixbus USA also services this route 5 times a week.
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- Website
- delta.com
Flights from Detroit to Chicago Midway International Airport
- Ave. Duration
- 1h 20m
- When
- Every day
- Estimated price
- $45–330
Flights from Capital Region International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 3h 36m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $50–340
Flights from Detroit to Chicago O'Hare International Airport
- Ave. Duration
- 1h 34m
- When
- Every day
- Estimated price
- $30–230
Flights from Detroit to South Bend
- Ave. Duration
- 1h 10m
- When
- Every day
- Estimated price
- $45–350
Flights from Detroit to General Mitchell International Airport
- Ave. Duration
- 1h 20m
- When
- Every day
- Estimated price
- $75–550
- Website
- aa.com
Flights from Capital Region International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 20m
- When
- Every day
- Estimated price
- $40–320
Flights from Detroit to Chicago O'Hare International Airport
- Ave. Duration
- 1h 32m
- When
- Every day
- Estimated price
- $30–230
Flights from Detroit to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 3h 22m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $85–550
- Website
- southwest.com
Flights from Detroit to Chicago Midway International Airport
- Ave. Duration
- 1h 13m
- When
- Every day
- Estimated price
- $45–330
- Website
- united.com
Flights from Detroit to Chicago O'Hare International Airport
- Ave. Duration
- 1h 32m
- When
- Every day
- Estimated price
- $30–230
Flights from Detroit to General Mitchell International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 3h 22m
- When
- Every day
- Estimated price
- $85–550
- Website
- spirit.com
Flights from Detroit to General Mitchell International Airport
- Ave. Duration
- 1h 14m
- When
- Monday and Friday
- Estimated price
- $190–550
Rome2Rio's guide to Amtrak
Contact 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
- $45–130
- Website
- https://www.amtrak.com/home.html
Train from Milwaukee to Glenview Amtrak Station
- Ave. Duration
- 1h
- Frequency
- Every 4 hours
- Estimated price
- $21–35
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 312-322-6777
- Website
- metra.com
Train from Chicago OTC to Winnetka
- Ave. Duration
- 38 min
- Frequency
- Hourly
- Estimated price
- $2–6
- Website
- https://metra.com
- 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 Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Ann Arbor to Chicago Bus Station
- Ave. Duration
- 5h 5m
- Frequency
- 3 times a day
- Estimated price
- $30–60
- Website
- https://www.greyhound.com/
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Ann Arbor to Chicago Bus Station
- Ave. Duration
- 4h 10m
- Frequency
- 5 times a week
- Estimated price
- $30–85
- Schedules at
- flixbus.com
- Phone
- +1 517-333-0400
- info@michiganflyer.com
- 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
- Michigan Flyer
- Child 2-16
- $7–9
- Adult
- $10–15
Want to know more about travelling around United States
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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 11:49 PM in Ann Arbor and 10:49 PM 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 26m to drive from Ann Arbor to Winnetka.
There are 218+ hotels available in Winnetka.









