There are 9 ways to get from Ann Arbor to Winnetka by train (Amtrak), bus (Flixbus), car, bus, plane, train, or bus (Greyhound)
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 (Flixbus)
cheapest- Take the bus from Ann Arbor to ChicagoFlixBus 2550
7h 17m$34–94Drive 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$56–358Bus via Battle Creek (Greyhound)
- Take the bus from Ann Arbor to Battle Creek Bus StopGreyhound US0160
- Take the bus from Battle Creek Bus Stop to Chicago Bus StationGreyhound US0160
8h 5m$62–110Drive 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 $30 - $95 and takes 7h 17m.
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 95th Red Line Station, State & Van Buren and Howard CTA Station. The journey, including transfers, takes approximately 7h 17m.
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 Flixbus 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 $30 - $95 and takes 7h 17m.
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, Flixbus USA operates a bus from Ann Arbor to Chicago 3 times a week. Tickets cost $28–90 and the journey takes 4h 10m.
Transport is disrupted due to the Russia-Ukraine war. Read more
- 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
- southwest.com
Flights from Detroit to Chicago Midway International Airport
- Ave. Duration
- 1h 13m
- When
- Every day
- Estimated price
- $45–330
- 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
- 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
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Ann Arbor to Chicago
- Ave. Duration
- 4h 10m
- Frequency
- 3 times a week
- Estimated price
- $28–90
- Schedules at
- flixbus.com
- Adult
- $28–90
- 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
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Ann Arbor to Battle Creek Bus Stop
- Ave. Duration
- 2h 5m
- Frequency
- 5 times a week
- Estimated price
- $27–60
- Website
- https://www.greyhound.com/
Bus from Battle Creek Bus Stop to Chicago Bus Station
- Ave. Duration
- 3h 50m
- Frequency
- 5 times a week
- Estimated price
- $29–45
- Website
- https://www.greyhound.com/
Want to know more about travelling around United States
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
Related travel guides
Travelling to the US: What do I need to know?
Read the travel guide
Why you should take the train in the US
Read the travel guide
Need to know: Greyhound
Read the travel guide
More Questions & Answers
Ann Arbor to Winnetka bus services, operated by Flixbus USA, arrive at Chicago station.
Winnetka is 1h behind Ann Arbor. It is currently 10:03 PM in Ann Arbor and 9:03 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.









